Mike’s Top Ten of 1999

In my mind, 1999 is one of the golden years of cinema. There are so many amazing movies that came out this year. And while it’s probably not all-time historically one of cinema’s absolute best years (though time is really the only judge of that), it’s the fact that it’s bolstered by a lot of movies from my childhood that makes me consider it as such.

This is also one of those years where I feel like most of us have at least 3-5 movies exactly the same on all of our top ten lists. Though I will also say, the other 3-5 are ones that feel hyper-specific to me and me alone. I doubt anyone but me would have this particular list as my top ten. Especially since you could go like 30 deep this year and get an amazing list out of it.

This is also one of the landmark years for a lot of reasons, most notably because the action genre was completely revolutionized this year and special effects took a giant leap forward. We also got a groundbreaking horror film, Star Wars came back, and, if you’re my age, there’s like 20 movies this year that you specifically remember from growing up that, in some way, had huge impacts on your life. It’s a really great way to end a decade/millennium.

Mike’s Top Ten of 1999

American Beauty

Any Given Sunday

Being John Malkovich

Bringing Out the Dead

Fight Club


The Matrix


Three Kings

11-20: Analyze This, Blue Streak, Bowfinger, Dogma, Election, For Love of the Game, The Insider, The Mummy, Office Space, The Talented Mr. Ripley

Tier two: American Pie, Audition, Beyond the Mat, Bicentennial Man, The Big Kahuna, The Blair Witch Project, Boys Don’t Cry, Deep Blue Sea, Fantasia 2000, Girl Interrupted, The Green Mile, The Hurricane, Life, The Limey, The Sixth Sense, South Park: Bigger Longer & Uncut, Star Wars Episode I: The Phantom Menace, Tarzan, Toy Story 2, The World Is Not Enough

Tier three: Angela’s Ashes, Arlington Road, Austin Powers: The Spy Who Shagged Me, Big Daddy, The Cider House Rules, Cradle Will Rock, Entrapment, Eyes Wide Shut, Galaxy Quest, Ghost Dog: The Way of the Samurai, Go, The Iron Giant, Mystery Men, October Sky, Sleepy Hollow, The Straight Story, Summer of Sam, Sweet and Lowdown, The Thirteenth Floor, The Thomas Crown Affair

Tier four: 10 Things I Hate About You, Anna and the King, Blast from the Past, The Boondock Saints, Chill Factor, Dick, Lost & Found, A Midsummer Night’s Dream, Music of the Heart, Never Been Kissed, The Ninth Gate, Play It to the Bone, Pokemon: The First Movie, Pushing Tin, She’s All That, Titus, Topsy-Turvy, Tumbleweeds, Varsity Blues, Wild Wild West

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1. The Matrix

“Do not try and bend the spoon. That’s impossible. Instead… only try to realize the truth.”
“What truth?”
“There is no spoon.”

It’s gotta be. There were periods where this wouldn’t have necessarily been my #1, just because #2 and #3 were also very big films in my life, but honestly, this has consistently always been there and I gain more appreciation for it as time goes on.

This movie really was a game changer for cinema. This movie was so good and was such lightning in a bottle that not even the directors could replicate it with two sequels. This movie is a perfect entity. Honestly if you watch it and pretend they never followed it up, you could do that.

I don’t know what there is to say about this movie. We all have this on our top ten. A lot of us have it at #1. No one’s gonna argue it at #1. The only question is where on the list you have it. I’ve seen this movie so many times that I watch it for little tics and pauses and random things that happen.

I also, no joke, think about this line and quote it at least once a week:

You can’t tell the story of the 90s in film without this movie. This is one of the five or ten most important films of the decade. And it’s also a perfect movie to boot. You rarely get that combination.

2. Fight Club

“You met me at a very strange time in my life.”

This was such a huge movie for me. I got so into this movie for a few years. And I was 11 when it came out. I’m not even sure I fully comprehended what it was that I liked about it, but I knew that I just loved it and watched it a bunch. Of course, now it’s one of those movies that I sort of put aside for a while as one of my “early days” movies that I didn’t want to hold me back from maturing as a movie watcher. But still, there’s no denying how integral this movie was to my filmgoing life.

David Fincher again, taking what’s not really a great book and turning it into a fantastic movie. Edward Norton and Brad Pitt star, and basically everyone knows the plot of this movie. You don’t really get into movies and make your way here without having seen this. It’s also the kind of movie that’s really difficult to try to explain without getting too deep into the plot. I could make a joke about the first two rules and yada yada yada, but I won’t. I’ll just say — chances are you know what this is about.

I’m really kind of amazed this movie holds together the way it does. It’s also a clear step forward for Fincher as a filmmaker, though I think it did get him into a few habits that manifested more in Panic Room, which lessens that as a movie for me. But even so, some of the things he does in this are absolutely tremendous, and he gets an absolutely committed performance from Edward Norton that sells the whole thing spectacularly.

Honestly, if you asked me to list the ten or twenty most important films of my middle school and high school, this would 100% be on that list and probably be in the top five.

3. Three Kings

Sit down. What do you see here?”
“Bunkers, sir.”
“What’s in them?”
“Stuff they stole from Kuwait.”
“Bullshit. I’m talking about millions in Kuwaiti bullion.”
“You mean them little cubes you put in hot water to make soup?”
“No, not the little cubes you put in hot water to make soup.”

I’m surprised I loved this movie as immediately as I did. I feel like I saw this almost as soon as it came out, and I absolutely loved it from the start. Which… it’s not because it’s great, it’s because I was so young. But I guess good movies do that. Sometimes you can like something even before you understand it.

This movie is one of David O. Russell’s masterpieces, and made me a fan of his for life. It’s just a wonderful piece of work. The plot revolves around three soldiers who find a hidden map while searching a guy and realize it leads to all the Kuwaiti gold that Saddam Hussein stole when they invaded. And this is all right at the end of the Gulf War, so the three of them, under little supervision, go out to find and take the gold back. It’s so good.

It’s perfectly written, and it’s just one of those movies you can go back and watch at any time and love. I watched this again recently and had that reminder of, “Oh yeah, this movie actually is perfect.” This is one of those — I would feel comfortable showing this to anyone because I would be confident they were going to love it.

4. American Beauty

“It’s a great thing when you realize you still have the ability to surprise yourself. Makes you wonder what else you can do that you’ve forgotten about.”

This movie blew my mind when I was a kid. Granted, maybe I shouldn’t have been watching it at age 11, but I did. And it really did a number on me. I never quite pinpointed it to specific things, but this feels like one of those movies that was instrumental in me deciding I wanted to be a writer. There was something absolutely wonderful about how this film was written, directed and acted. I remember — and this is before I got into the Oscars themselves — rooting really hard for this to win Best Picture that year. I was so into this movie.

It’s about Kevin Spacey as a guy who has a midlife crisis. He just hates his life and can’t stand the monotony of it all. And then one day, while watching his daughter’s hot friend perform a cheerleading routine, has an epiphany. And suddenly he just starts to behave differently, which causes upheaval around everyone around him and eventually leads to (don’t worry, it’s part of the opening voiceover, so you know going in) his death. It’s… it’s really good. Spacey rightly won an Oscar for his performance. Annette Bening should have also won. And Chris Cooper should have been nominated. (And maybe even Allison Janney, for that matter.) It’s just a wonderful movie that still holds up for me. I know it might feel cheesy to some, but I think this is one of those movies that created its own cliche.

I really just adore this movie, and while I’m not really sure where this is gonna end up after more time passes, I can definitely say that this is one of my absolute favorite movies of the decade.

5. Bringing Out the Dead

You said if I came in late for another shift, you’d fire me.”
“I’ll fire you tomorrow.”

This is the best of the forgotten/overlooked Scorsese movies. King of Comedy is like, the celebrity overlooked movie. But this is the real overlooked movie of his. I grew up loving this movie and watching it all the time, and yet still I find people who know nothing about that or go, “Is that the one with the ambulances?”, and that’s all they know.

It’s a movie about ambulance drivers, based on a novel by a writer who actually worked as a paramedic for some time. It’s Scorsese’s fourth collaboration with Paul Schrader (after Taxi Driver, Raging Bull and Last Temptation of Christ). Nicolas Cage stars as a paramedic, burned out by the job and haunted by the people he was unable to save (which has been everyone over the past couple of months). That’s really all you need to know. It’s mostly a lot of him and his fellow paramedics going on the job, night to night, with some people/patients recurring and other random, crazy events. John Goodman, Tom Sizemore and Ving Rhames play the other paramedics. Rhames gives an amazing performance, with his best scene happening in a club as a teen overdoses. Goodman is just quietly great, and Sizemore plays a complete psycho, which… yeah. Cliff Curtis is also in this and is fantastic as well.

I really love this movie. If I’m being honest, I’d probably watch this over Taxi Driver, if you gave me the option. Not that I think it’s a better movie by any stretch, I just would watch it first. This is one of those movies that’s comfort for me. I can just put it on and enjoy it any time of day. Pound for pound, it might be Scorsese’s most underrated movie. Because some of the underseen ones… I get that not everyone would enjoy them. This one feels like one everyone would like, which is why it’s so strange to me that it’s not widely known as most of the others.

6. Payback

“Not many people know what their life’s worth is. I do. Seventy grand. That’s what they took from me. And that’s what I was going to get back.”

I saw this movie in theaters, and must have seen it a couple dozen times. I love it so much. I know a few years after it came out, they released a director’s cut that’s closer to what Brian Helgeland wanted. But honestly, I prefer this version. The third act is flawed, but I love the rest of it so much that I don’t even care.

It’s a remake of Point Blank, but looser. Simple premise: man was duped out of $70,000 by his wife and former criminal partner, shot and left for dead. And now he’s back, and he wants his money. So he basically goes on a spree, messing people up for his money. The beauty of the movie is that he keeps working his way up the criminal chain to get his money, and each time they keep being dumbfounded at the idea that all he wants is the $70,000 and nothing more. Like, “You’re gonna get yourself killed for that little money?” It’s awesome.

Mel Gibson stars, Gregg Henry plays the partner (in one of his best film roles, marking him as a thoroughly underrated character actor). Maria Bello plays a hooker Gibson’s character used to drive for. Deborah Kara Unger plays Gibson’s wife. Lucy Liu plays a hooker, in her first semi-major film role. David Paymer is in this, and then there’s James Coburn and Kris Kristofferson in fun cameos. It wasn’t Kristofferson originally, but they brought him in during reshoots. As I said, the third act is flawed and rushes a conclusion together. But honestly, I don’t care. I love this movie. It’s so much fun. I can always put this on and have a good time.

7. Being John Malkovich

“There’s a tiny door in my office, Maxine. It’s a portal and it takes you inside John Malkovich. You see the world through John Malkovich’s eyes… and then after about 15 minutes, you’re spit out… into a ditch on the side of the New Jersey Turnpike.”
“Sounds great! Who the fuck is John Malkovich?”

This is the movie that gave us Charlie Kaufman. And for that we all should be grateful.

It’s one of the most insane premises you’ll ever hear: a man finds a mysterious door in an office building that leads to a portal inside John Malkovich’s head. The fact that Malkovich was cool with it and even agreed to appear in the movie is also quite awesome. John Cusack stars, with Cameron Diaz, Catherine Keener, Orson Bean, and of course, Malkovich. It’s just great. I think Charlie Kaufman has outdone himself with his later work, but man, what a hell of a first movie. Also directed by Spike Jonze, who at the time of this posting has directed four movies and all of them are perfect.

8. Man on the Moon

“Andy, you have to look inside and ask this question: who are you trying to entertain – the audience or yourself?”

So fun story: this was not originally in the top ten for this year. I’ve always loved this movie, but when I made up the initial list, I had it in the 11-20, as an unofficial #11 of sorts. And then, randomly, last Thanksgiving, I was up late one night and happened to switch over to this movie as it was playing, and it reminded me just how much of a masterpiece it is.

It’s a biopic of Andy Kaufman starring Jim Carrey. In a way, this is Jim Carrey’s greatest performance. But also, in getting that… we also got… well, a good companion piece to the movie is the documentary Jim & Andy. It was widely known what happened on the set of this movie, but the documentary actually brings it all out there and has everyone talk about it publicly. Doesn’t add or take away from the work itself, but it does give you something really interesting to watch alongside it.

Anyway, Carrey is electric as Andy Kaufman, and it’s Milos Forman following up The People vs. Larry Flynt with another incredible biopic (written again by the offbeat biopic masters, Scott Alexander and Larry Karaszewski). Andy Kaufman was truly a one-of-a-kind person, and this is the biopic he deserves. And it’s one of those where, even I forgot how amazing it was for all these years. I’m so glad I ended up watching it again so I could have it on this list where it properly belongs.

9. Any Given Sunday

“On any given Sunday you’re gonna win or you’re gonna lose. The point is – can you win or lose like a man?”

Most people wouldn’t say this is a good movie. A lot of people openly dislike this movie. I’ve always loved this movie because it’s one of those I grew up with and watched a bunch when I was in middle school. So here we are.

It’s Oliver Stone’s football movie, which, in case you weren’t sure about the metaphor of football being war, don’t worry, the movie will tell you. I tend to ignore all that stuff and just focus on what’s in front of me. It’s about a once-great franchise struggling to make the playoffs. And the main players are Cameron Diaz as the team owner, Al Pacino as the coach, Dennis Quaid is the aging QB and Jamie Foxx is the up-and-coming, Michael Vick-like QB who takes over for Quaid when he gets injured. Theres also James Woods, LL Cool J, Ann-Margret, Lawrence Taylor, Aaron eckart, Matthew Modine, John C. McGinly, Jim Brown, and Charlton Heston as the commissioner.

The NFL wouldn’t go anywhere near the movie, so all the teams are fictional (the Miami Sharks is the name of the team they’re all on), and Stone amalgamated like three scripts to form what the final product. So I get that it’s a flawed movie. But also, I love it.

10. Magnolia

This is Paul Thomas Anderson’s most indulgent film. That’s not to say it’s not great. But it’s definitely the one that most feels like “director porn.” You know what I mean? It’s definitely the one of his that feels like it’s gonna have the most detractors just because it’s the one that feels most like an up and coming filmmaker giving in to all the early instincts that you think about when you’re first writing stuff. Still, though… it’s amazing.

It’s a huge ensemble movie, about all of life’s little coincidences, featuring like a dozen main characters whose lives are all intertwined in some way. It’s impossible to discuss a plot, but it’s full of great actors and great performances. The most notable is Tom Cruise, who plays a motivational speaker who gives speeches about picking up women but has a secret past he doesn’t talk about. Then there’s Jason Robards as a dying man being cared for by Philip Seymour Hoffman, and Julianne Moore, his daughter, who is secretly addicted to prescription pills. Then there’s John C. Reilly as a nice cop who starts romancing Melora Walters. Then there’s Philip Baker Hall as a dying game show host, William H. Macy as a former child whiz kid. And somehow it’s all set around Aimee Mann music, complete with a music video in the center of the film in which all the characters sing along to one of her songs.

It’s a fantastic movie. I feel like it’s the one of his (save his first one) that I’d want to go back and watch the least, but it really is a tremendous movie. And the performances are really spectacular. Anderson always gets great performances, but this one is really an actor’s paradise, with a lot of them seemingly playing against type in a lot of ways, which makes the results all the more special.

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Analyze This — One of the great comedy premises of all time. And I’m not even talking about the plot so much as I’m talking about the idea to put De Niro in this role. De Niro plays a mob boss who starts getting panic attacks and has to see a psychiatrist. But of course he’s worried about his image and what it would do if people find out he’s doing so. But really the film is about the relationship he has with his psychiatrist, played by Billy Crystal. The pairing of the two of them is wonderful, and leads to a lot of laughs. They make this movie special, and it’s one of the great comedies of the 90s.

Blue Streak — Martin Lawrence. I watched this movie a ton when I was a teenager. He plays a criminal who stole a bunch of diamonds, but then gets caught before he can escape. So he duct tapes them inside the vent of the building and surrenders. A ew years later, he’s out and goes back to the building to get the diamonds. Only… the building is now a police station. So now he’s gotta pretend to be a cop long enough to get up in the vent and get the diamonds. Of course, the joke is that he actually has to do real cop stuff, encounters some of his old friends, and actually gets kinda good at the whole cop thing. It’s great. I love this movie.

Bowfinger — The last of the good Eddie Murphy movies. After this it’s all Pluto Nash and family stuff and watered down versions of his best stuff. (Yes, Dreamgirls is good. But he’s good in it more so than it’s his movie.) Steve Martin wrote it, and it’s just hilarious. He plays a movie producer desperate for a hit who wants to hire Murphy (playing a huge movie star) to be in it. But the Murphy character’s head is too big and is too deep into scientology (it’s not… but it is) to do it. So Martin decides to shoot the movie around him without him knowing. And then, for the actual scenes, he gets his nerdy brother to pretend to be him. It’s so good. Heather Graham plays the script girl who slowly sleeps her way up to being the lead of the movie… it’s amazing. Everyone should see this movie.

Dogma — Kevin Smith’s ode to his Catholic upbringing. It’s so great. Pound for pound, this might be his best movie. It’s about a pair of angels who were banished from heaven who discover a loophole that will allow them to get back in. Only, if they do, it will negate all of existence, so the last descendant of Jesus (who now works at an abortion clinic) goes on a journey to stop them. It’s great. Damon and Affleck play the angels, Alan Rickman is the messenger of God, Jay and Silent Bob are prophets, Chris Rock is the 13th apostle, Salma Hayek is a muse… George Carlin is a cardinal! It’s great. I love this movie.

Election — The movie that broke Alexander Payne. And Reese Witherspoon, for that matter. It still holds up. Matthew Broderick plays a high school teacher in the middle of a class election. Reese Witherspoon is the overachieving valedictorian who of course is going to win. But Broderick can’t stand her, so he works behind the scenes to get a popular jock to run against her. It’s so good. Every Alexander Payne movie is worthwhile. This is one of the best of them.

For Love of the Game — This is one of those movies with an incredible premise that I almost wish were slightly better, just so it could be a classic. Because it doesn’t really use the premise in the best way, but it’s still a good movie. It just… okay, so it stars Kevin Costner as a pitcher on his last legs playing a meaningless game at the end of the season. He’s played his entire career for the same team, but now the new owner is about to get rid of him next year. And the movie takes place over the course of the day/game, as he starts pitching what could be a perfect game. And in the middle of it, he thinks back to his relationship with the love of his life, and we see flashbacks in between batters he faces. Sam Raimi directed this, and it’s a hell of a movie. I like sentimental movies, but even I’d admit that it might be a bit too sentimental at times. I feel like, were it just slightly different tonally, this would be ranked among the all time best sports movies. I’m not even sure it’s in the top ten baseball movies. Though baseball movies are generally strong. Still, I love this, though I get that this might appeal to me more than it might other people. Still, Costner doesn’t just pick any sports movie. Generally they have the goods. And this has the goods.

The Insider — Michael Mann drama about Russell Crowe as a tobacco company executive who decides to whistleblow about the fact that his company (and all the tobacco companies) knew the product was harmful yet decided to sell it anyway. And the film details both his decision to do this as well as the repercussions of it and CBS’s decision to air it, and the legal battling that ensues. Great performances all around. It’s a riveting film that rightly was nominated for Best Picture. It barely missed the top ten, but this is a year with so much great stuff that came out. So something had to get squeezed. But trust me, this would be a top ten movie in another year.

The Mummy — Brendan Fraser, baby. This is a fun action-adventure remake of the 1932 horror movie, and man, does it hold up. A bunch of archaeologists find a hidden chest that happens to contain the vengeful spirit of a dead Egyptian High Priest. He gets out and starts praying on all those responsible and raising armies of the dead. As you do. And it’s up to Brendan Fraser and Rachel Weisz to stop him. I honestly don’t know what to do with someone who hasn’t seen this movie. Do you not like to have fun?

Office Space — What a classic. Everyone my age remembers this movie. One of the cult films of the 90s. No one saw this in theaters, but we all owned the DVD. Mike Judge, baby. The classic movie about how shitty it is to work a dead end corporate job. A must see for everyone. I honestly struggled to figure out what gif to put here, since there are so many options. Do I go Lumberg, do I go Milton, do I go them smashing the printer? There are so many options. So I’ll just go with this, since I quote this one at least once a month:

office space GIF by hero0fwar

The Talented Mr. Ripley — This movie is so good. I forget how good this is until I watch it again. This is Anthony Minghella’s followup to The English Patient. Based on the Patricia Highsmith Ripley novels. And it’s great. Matt Damon plays Ripley, and it’s about him being sent to Italy to get Jude Law, a rich playboy galavanting around Europe. And… really it’s best if that’s all you know. Because it’s really good. Damon’s great. Law is fantastic. Philip Seymour Hoffman is very good. Cate Blanchett is good. This is one of the more underrated movies of the 90s

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Tier two:

  • American Pie
  • Audition
  • Beyond the Mat
  • The Big Kahuna
  • The Blair Witch Project
  • Boys Don’t Cry
  • Deep Blue Sea
  • Fantasia 2000
  • Girl, Interrupted
  • The Green Mile
  • The Hurricane
  • Life
  • The Limey
  • The Sixth Sense
  • South Park: Bigger Longer & Uncut
  • Star Wars Episode I: The Phantom Menace
  • Sweet and Lowdown
  • Tarzan
  • Toy Story 2
  • The World Is Not Enough

Star Wars Episode I: The Phantom Menace was, at the time, the biggest movie in the world. After sixteen years, we got more Star Wars. I had barely even seen the originals when this came out and even I saw how huge a deal it was. And… when I was 11, I enjoyed the movie. Even now, I’ve got a certain attachment to it. It’s still got one of the greatest pieces of score in film history:

The Limey is one of the most underrated Steven Soderbergh movies. He made it between Out of Sight and Traffic/Erin Brockovich, and it just kind of got lost. Terrence Stamp plays a British man who comes to Los Angeles to find the person he thinks is responsible for killing his daughter. It’s short, it’s indie, it’s told out of order, and it’s awesome. One of the most essential Steven Soderbergh movies, and one of the real gems of the 90s that is ridiculously underseen. Sweet and Lowdown is one of the Woody Allen movies I like. It’s in that moderate thumbs up section. It’s a fake biopic of a jazz guitarist played by Sean Penn. And he’s a son of a bitch but a great guitarist. And we follow him as he screws up his life and falls for Samantha Morton, a mute woman. Penn is good here and Morton is fantastic. They’re the highlights of this one. Boys Don’t Cry is based on the Brandon Teena story. A trans man moves to a new town and begins hanging out with some roughnecks, and falls for one of their sisters. Hilary Swank won her first Oscar for this performance, but to me its Chloe Sevigny who really steals the show.

Deep Blue Sea is one of the great shark attack movies of all time. It’s about a group of scientists in an underground lab, trying to find a cure for Alzheimer’s. And in doing so, they find a way to make sharks’ brains bigger, which really only makes it worse when they break loose and attack. So now you have sharks attacking these people who have to escape this lab, which is underwater, and not die. It’s great. And it features one of the great Samuel L. Jackson monologues of all time. The Sixth Sense was so fucking big in 1999. The worst part about it was, after the initial craze about this, it got relegated into a “spoiler” movie. Like The Crying Game was. And it took a couple of years for people to go back and realize… it’s actually quite good on its own terms. The twist is the twist, but everything around it is quite solid. It’s definitely the best writing M. Night Shyamalan’s ever done. Also, for those who’ve not watched it in a while and have figured it was a “one twist pony” kind of movie… give it a shot again. It’s more solid than you think. Audition is one of those movies — if you haven’t seen it and/or don’t know what it is (and I’m always surprised at how many people that is), just watch it. Trust me. It will be an experience you do not forget. Here’s all you need to know: a widower starts auditioning women to be his new wife. Start there and just watch it. It’s… something.

Fantasia 2000 is a very worthy sequel. I like that they did a sequel to this in particular, because it’s about music and animation and the blending of the two. I’m hoping they make another one in the next twenty years. Because these movies are fantastic. They do repeat Sorcerer’s Apprentice in this, which is to be expected. But everything else here is new, and follows the general structure of the original. The opening has Beethoven’s Fifth, set to abstract colors and images. Then there’s the flying whales one, the one with the toy soldier in the toy shop, the flamingos using yo-yos, Noah’s Ark with Donald Duck. The two best ones are the last one, which is the one about the forest spirits and the great fire, and Rhapsody in Blue, which features brilliantly hand-drawn images of New York City, inspired by Al Hirschfeld. That’s the best. That’s worth the price of this entire film on its own. The Blair Witch Project was a phenomenon. The first virally marketed horror movie, that dropped at the perfect time, just before the internet took off and ruined the novelty of these things. I’m sure, at the time, no one of a certain age really fell for the “this really happened” aspect. But I was 11. And I was willing to go along. It certainly made the viewing experience more fun. I still remember where I sat while watching this movie. It was a big deal in my film development. And, I doubt this movie remotely holds up. But it was such a cultural phenomenon in 1999 that cannot be overlooked. Girl, Interrupted is a story about girls in a psych ward. Winona Ryder plays a girl institutionalized after a suicide attempt and it’s about her experiences on the ward with the other girls. The movie’s best remembered by featuring the breakout performance by Angelina Jolie, who won an Oscar for it. She really does command the screen here, even if it still is Winona’s movie.

South Park: Bigger Longer & Uncut is the movie. Crazy they got a movie that came out during their third season and still managed to keep going for another twenty years. And they were still putting out episodes while making the movie. Which is insane. I remember seeing this — my sister was on a girl scout camping trip with my mother for the weekend. So my father and I went to the racetrack for the day with my neighbor and then that night, somehow I convinced him to take me to this. And it was like, a 10 or 11 o’clock showing, and it was me, an eleven-year-old, my father, and basically college kids watching this movie. I’ll never forget that. Anyway, this movie is a lot of fun. They’ve done longer episodes similar to this before, but nothing quite like this. I still remember large sections of this movie. And the songs — the songs are amazing. The opening Disney parody, “Mountain Town,” “Uncle Fucka,” “It’s Easy, Mmmkay,” “Blame Canada” (which was nominated for an Oscar!), the extended “Kyle’s Mom’s a Bitch,” “What Would Brian Boitano Do,” “Up There,” Satan’s “Ariel” song, and of course, my personal favorite, “La Resistance,” which is so perfectly Les Mis. I haven’t watched this movie in at least 15 years and I can still pretty much quote every lyric from all those songs. The Hurricane is a biopic of Rubin Carter. He was the subject of a Bob Dylan song in 1976 and a boxer who was thrown in jail for a triple murder, despite some questionable police tactics. The film talks about all of that, and has one of Denzel’s greatest performances. When ranking his best performances, this and Malcolm X almost always take the top two spots. He’s so good here.

The Big Kahuna is a movie I somehow stumbled upon on cable before I really got into movies and just watched it a lot. And I love this movie. It’s basically a play on film, reminiscent of Death of a Salesman. Kevin Spacey and Danny DeVito hang out in a hotel room with a younger client and discuss pitching their product to a big CEO. And it’s just them shooting the shit in a hotel room. It’s great. One of my favorite hidden gems. The Green Mile is Frank Darabont doing Stephen King again after Shawshank. Though while that one was a straight prison movie, this one has the fantastical element to it on top of that. Michael Clarke Duncan plays a man who is put on death row for murdering two young white girls. And the film is about the effect he has on everyone that’s in that wing of the prison, especially the guard in charge of the row, Tom Hanks. The cast here is nuts, David Morse, Bonnie Hunt, James Cromwell, Michael Jeter, Graham Greene, Sam Rockwell, Barry Pepper, Jeffrey DeMunn, Patricia Clarkson, Harry Dean Stanton and Gary Sinise. It’s a really solid movie. Doesn’t quite hold up like Shawshank does, but it’s still really good. Beyond the Mat is a wrestling documentary. And, while I always liked it because I was into wrestling big time when it came out (as all kids in the late 90s were), I think this one holds up because it’s the first (and maybe only) wrestling documentary that really gets into the people behind the scenes. Toy Story 2 is the sequel. I got into movies with this being proclaimed as the best one and all that. I never quite understood that. It was always my least favorite. That said… it’s Pixar and it’s great. It would be the Toy Story movie I put on last of the initial trilogy, but there’s just something so comforting about these toys.

Life is one of the great 90s comedies. Eddie Murphy and Martin Lawrence. They play two men who are framed for murder and end up in a southern prison with life sentences. And the film is about their time in prison. And it’s great. This movie still holds up. This is really the last of Eddie Murphy being great before family movies got to him. This and Bowfinger. I cannot recommend this movie highly enough. The World Is Not Enough is Pierce Brosnan’s third Bond movie. Probably the second best of his. Has Robert Carlyle as a cool villain, Sophie Marceau, the return of Robbie Coltrane, and Denise Richards as Dr. Christmas Jones. Also a fantastic sendoff for Desmond Llewelyn as Q. Definitely very solid, as Bond movies go. Tarzan is Disney. Technically post-Renaissance, because I think the power structure of the company changed and different people were involved. Still part of that run of great movies, though. It’s hard to care about Tarzan given how often we’ve seen it on screen, but they do a great job here of making it work. Plus, fantastic Phil Collins soundtrack on this one. American Pie is the quintessential teen sex comedy of the 90s. Super iconic, and it made stars of the cast, if only for a brief while for some of them. Famous for the pie fucking scene and for the immortal line “This one time, at band camp…”

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Tier three:

  • Angela’s Ashes
  • Arlington Road
  • Austin Powers: The Spy Who Shagged Me
  • Big Daddy
  • The Boondock Saints
  • The Cider House Rules
  • Cradle Will Rock
  • Entrapment
  • Eyes Wide Shut
  • Galaxy Quest
  • Ghost Dog: The Way of the Samurai
  • Go
  • The Iron Giant
  • Mystery Men
  • October Sky
  • Sleepy Hollow
  • The Straight Story
  • Summer of Sam
  • The Thirteenth Floor
  • The Thomas Crown Affair

The Straight Story is a David Lynch movie about a man who, after finding out his estranged brother is dying, hops on a tractor to drive cross country to see him. That’s it. That’s the movie. Stars Richard Farnsworth, a longtime stuntman who occasionally acted, finding himself nominated for two acting Oscars in his career (Supporting Actor for Comes a Horseman in 1978 and lead for this), and it might be the most straightforward movie Lynch has ever directed. It’s got a real sweetness to it. Eyes Wide Shut is Stanley Kubrick’s last movie. Tom Cruise, Nicole Kidman. Very weird, but very good. Austin Powers: The Spy Who Shagged Me is the sequel, and arguably funnier than the first one. I definitely watched this one more. It’s got Heather Graham instead of Elizabeth Hurley, and has Meyers playing a third character, Fat Bastard. Somehow that worked. I don’t understand it, but I just go with it. These movies somehow worked. And I think they still do. The Thomas Crown Affair is a really fun remake with Pierce Brosnan and Rene Russo. It’s no Steve McQueen and Faye Dunaway, but it has its place. It holds up. It’s a lot of fun. Go is one of those Tarantino-inspired movies of the 90s. It’s about a drug deal and its aftermath told from several different perspectives. It’s a lot of fun. Cradle Will Rock is written and directed by Tim Robbins. It’s about a play being put on in the 30s with very communist overtones and the pressure the troupe and actors face from the government to not put it on. Great cast here — Hank Azaria, Bob Balaban, Jack Black, Ruben Blades, Joan Cusack, John Cusack, Cary Elwes, Paul Giamatti, Philip Baker Hall, Bill Murray, Vanessa Redgrave, Susan Sarandon, John Turturro and Emily Watson.

The Thirteenth Floor is a movie I remember really enjoying when I was 11. I remember, we were all spending the night at one person’s house, and we went to Blockbuster earlier that night. And we rented The Matrix and this. And I remember watching this at like 3 in the morning and really enjoying it. It’s about a guy who has created an entire VR simulation of 30s Los Angeles. But he gets murdered, and all the evidence points to his protege, to the point where even he starts to think he may have done it. So now he has to figure out what happened to try to clear his name. I haven’t seen this in years, but I really liked it at the time. I really wanna go back and see this because I have a feeling this could jump way up on this list if I rewatched it properly. The Boondock Saints is one of those movies that was, for my generation, the hallmark movie for people whose movie opinions annoyed the shit out of you in high school. There were always those kids who constantly talked about what an amazing movie this was, and basically had seen nothing else and just annoyed the shit out of you when you were in that stage of starting to uncover all the really cool movies that are like, second tier movie buff movies. This was that movie for my middle school and early high school. Then it became Donnie Darko for high school, and then it became The Big Lebowski for college. Though by that point it was more, “Are you still only talking about that movie? There’s other stuff out there.” The others were like, “Of course that’s your one movie you reference.” Anyway, this is a Quentin knockoff that tells is action scenes in flashback. Basically it’s two Irish guys who start to kill mobsters as sort of avenging angels. It’s… it’s fine. It’s fun and it’s perfectly entertaining. That was partially why I always got annoyed with people, because they’re treating a perfectly fine movie as the greatest thing ever and you’re just like, “Can you watch more stuff so we can put this all in perspective?” Anyway, fuck those people. The movie’s fine.

The Iron Giant is Brad Bird’s first movie, and one that people swear by as a masterpiece. I’m not quite there, but I do enjoy it. Basically it’s E.T. but with a giant robot. A kid befriends the robot and hides him from the government, who wants to destroy it. It’s only 80 minutes, and it’s really solid. October Sky is a great family movie about a kid who decides he’s gonna build a rocket. And it’s one of those 1950s small town kind of movies (Sandlot, etc) that were commonplace in the 90s. And it’s mostly a father-son story. Chris Cooper plays the dad and he works in a coal mine and doesn’t see why his son is wasting his time with this science stuff. It’s very uplifting and one of those movies that will have you liking it by the end. Galaxy Quest is basically Three Amigos but with Star Trek. The cast of a Star Trek like show reunites at a Comic-Con and then are taken by a real alien species who saw their show and thinks they’re the only people who can help save them from an evil species. Tim Allen, Sigourney Weaver, Alan Rickman, Tony Shalhoub, Sam Rockwell — this is one of the great comedies of the 90s. Entrapment is… basically The Thomas Crown Affair? Catherine Zeta Jones works for an insurance company and Sean Connery is a thief. She convinces her company to track him down. She embeds herself with him (figuratively and literally), and both start stealing stuff together. And it’s twisty — who’s conning who — and it’s fun.

The Cider House Rules is, if I were ranking the top five “Harvey Weinstein Oscar bait movies of the 90s,” one of the movies I would put on that list. (The Piano is on there. Chocolat, though technically 2000, is on there. Shakespeare in Love probably has to be on there, even though to me it’s the movies that are more Oscar bait than good, and Shakespeare in Love I actually think is very good. The English Patient probably is on there too. Maybe Il Postino as five?) Stars Tobey Maguire as an orphan who grew up in an orphanage run by Michael Caine, a nice doctor who on the side is addicted to ether and performs abortions. He’s groomed to take over, but decides he’s gonna go out and see the world for a while. So he ends up on Charlize Theron’s family’s farm, picking apples. And the film follows his romance with Charlize while her husband (Paul Rudd) is off at war, and the black family who also works on the farm. It’s written by John Irving, who also wrote World According to Garp. It’s solid. It’s a very good movie. I always cringe a little when thinking about it because of the whole Oscar thing, but the movie itself is quite solid. Sleepy Hollow is Tim Burton doing Ichabod Crane. With Christopher Walken as the Headless Horseman. Aww yeah. It’s good. The set design is incredible and it feels like vintage Tim Burton. Not my favorite of his movies, but it’s definitely one of those… it’s really worth seeing. It’s top tier Burton. Ghost Dog: The Way of the Samurai is Jim Jarmusch making a modern day samurai movie with Forest Whitaker. Is that something you might be interested in? It’s basically Le Samourai meets The Professional. But it’s good.

Big Daddy is Adam Sandler doing a comedy mixed with dramatic moments. This is probably the one I saw the most of growing up. This and Happy Gilmore. He plays a guy who refuses to grow up who suddenly finds himself in the care of his roommate’s alleged son, who forces him to grow up. It’s cute. It’s the most adult Adam Sandler got before Paul Thomas Anderson got involved. Arlington Road is a really interesting movie that’s really quite solid. Jeff Bridges plays a professor who starts to think his nice neighbors are secretly terrorists. It’s… very much worth seeing. Definitely 90s, but done in the vein of those 70s paranoia thrillers, and I love that about it. Honestly anything with that Rear Window type plot that manages to stick the landing is all right by me. Definitely recommend this one. Summer of Sam is Spike Lee’s movie about the Son of Sam. Mostly it’s about the craziness that surrounded that summer, with his usual cast of people in Brooklyn. The cast is nuts, and it mostly is interesting. Though it’ll never go down as one of the “great” Spike Lee films. Angela’s Ashes is one of the great memoirs of all time. Frank McCort. I’d say read the book before you do anything else. But the movie is also quite solid. It’s not the book, and can never approach the book, but it’s still a very solid and worthwhile movie.

Mystery Men is one of the craziest movies that ever got made, and I can’t believe it exists, but I love every minute of it. It’s about a bunch of wannabe superheroes (without any real powers) who want to save the city… only to be constantly upstaged by basically the Superman of the city. Only, when that hero gets captured, it’s finally up to them to save the day. Again, it’s nuts and I can’t imagine this holds up, but when I was 11, this movie was the shit. And it will be forever immortalized as the movie that brought us this song (and yes, that is who you think it is at the beginning of the video):

Tier four:

  • 10 Things I Hate About You
  • Anna and the King
  • Blast from the Past
  • Chill Factor
  • Cruel Intentions
  • Dick
  • Lost & Found
  • A Midsummer Night’s Dream
  • Music of the Heart
  • Never Been Kissed
  • The Ninth Gate
  • Play It to the Bone
  • Pokemon: The First Movie
  • Pushing Tin
  • She’s All That
  • Titus
  • Topsy-Turvy
  • Tumbleweeds
  • Varsity Blues
  • Wild Wild West

Pokemon: The First Movie. I saw this shit in theaters. Mewtwo vs. Mew, Ash almost dying. This shit was fun as hell. And they had that Pikachu short in front of it where they revealed Togepi. Wild Wild West is one of the great disasters of all time. And I enjoyed the shit out of it. It’s too expensive, too insane, and just a damn good time. Will Smith and Kevin Kline trying to stop a former Confederate general from killing the president. It’s… so goddamn insane. And yet… I have a soft spot for it. Also it’s still one of the greatest punchlines ever (if you haven’t seen this story, you should). 10 Things I Hate About You is a movie I saw almost 20 years late. It’s Taming of the Shrew in high school with Julia Stiles, Heath Ledger and Joseph Gordon-Levitt. Really great as far as high school rom coms go. Chill Factor is such an insane premise. Basically… Speed, but with a chemical weapon. There’s a bomb that’s on an ice cream truck, and if it’s not kept below a certain temperature, it will explode. Stupid as shit, but I enjoyed the hell out of it. Titus is Julie Taymor doing Titus Andronicus. Looks awesome. She’s great for making movies that look visually stunning. Kinda wish they let her do more movies, but also… maybe not Shakespeare. It’s cooler when she makes Beatles musicals and artist biopics.

Varsity Blues is that movie we all remember with the whipped cream bikini and the immortal line, “I don’t want your life.” Honestly I don’t remember a whole lot about the plot except that James Van Der Beek didn’t wanna follow in his father’s footsteps and their teacher ended up being a stripper. But it’s high school football in Texas and it’s one of those movies people my age just kind of saw and liked. A Midsummer Night’s Dream is a fun update. Still not as good as the 1935 version with all those special effects, but amusing. This one stars Kevin Kline, Michelle Pfeiffer, Rupert Everett, Calista Flockhart, Christian Bale, David Strathairn, Sam Rockwell and, most importantly, Stanley Tucci as Puck. Cruel Intentions is your classic teen incest movie. Well, okay, it’s Dangerous Liaisons in high school. But also incest. Ryan Philippe and Sarah Michelle Gellar. They’re step-brother and sister and he’s able to sleep with anyone he wants… except her. And she makes him a deal — deflower the dean’s daughter, and she’ll sleep with him. Only the dean’s daughter, Reese Witherspoon… he actually kinda falls in love with her. Which was not part of the plan. It’s Dangerous Liaisons. So you know the plot. It’s… it’s a big movie for people around my age. I never really cared for it, but it’s also one of those movies I always hold in reasonable esteem just because it’s one of the markers for my childhood.

Lost & Found is a movie I saw way too much of as a child. David Spade and Sophie Marceau star. He plays a dude trying to impress his hot neighbor, so he steals her dog, thinking, “Well, if I bring it back, I’m a hero.” Naturally, things don’t work out as expected and comedy ensues. Play It to the Bone is another Ron Shelton sports movie. Not quite on the level of his previous ones, but still fun. Woody Harrelson and Antonio Banderas play boxer best friends who get an offer to fight each other on the undercard of a major fight. They need the money so they decide to take it. Along for the ride comes one of their girlfriends (formerly the girlfriend of the other one). It’s fun. Tumbleweeds is Janet McTeer as a wayward mother who cannot stay in one place for more than the length of a failed relationship. Which certainly makes life hell on her daughter. It’s a really interesting mother-daugther story with a take-notice performance from McTeer. Music of the Heart is a Wes Craven movie. Which is the most interesting thing about it. Meryl plays an inner city music teacher trying to teach violin to the kids. So… Scales and Deliver? You know the type. It’s Wes Craven’s only real foray into non-horror, and it’s interesting. Dick is basically if you said, “What if Romy and Michelle foiled Watergate?” Michelle Williams and Kirsten Dunst play two girls who have no idea what is going on but somehow are the reason Nixon goes down. It’s dumb comedy, but fun.

Never Been Kissed is Drew Barrymore as a reporter who goes undercover in high school and sort of gets to relive high school in a better way than she did before. Weirdly I can remember almost nothing from this movie except a scene where David Arquette eats an entire tub of coleslaw. Anna and the King is a redo of the 1946 version, or, for most people, The King and I without the music. Jodie Foster plays Anna and Chow-Yun Fat plays the King. Costumes look great. It’s one of those expensive, lavish, totally fine Hollywood remakes. Topsy-Turvy is Mike Leigh’s two-and-a-half hour movie about Gilbert and Sullivan. Get hyped! It’s Shakespeare in Love, but for The Mikado. Aww yeah! The thing about Mike Leigh… I don’t always love his movies, but they always have certain redeeming qualities that make me not want to write them off. This one is about the sets and costumes. It looks great. And it is interesting. Still, his movies are an acquired taste, so it’s not for everyone.

Pushing Tin is an interesting dark comedy about air traffic controllers. I know, another one of those. John Cusack is the one that’s been there forever and is basically the one who owns everything. And then in strolls Billy Bob Thronton, who is every bit as cool as Cusack but makes it look effortless. Naturally a one-sided rivalry ensues and it causes Cusack’s life to spiral out of control. Mike Newell directs and a good cast — Cate Blanchett, Angelina Jolie. It’s weird but fun. Blast from the Past is a really fun premise. 1950s Family thinks nuclear war is upon us and go into a bomb shelter. 30 years later, they come out. So now their son is an adult and has no idea what the modern world is like. Naturally, that man is played by Brendan Fraser, who made a career playing dudes who come into society. Still, it’s fun. The Ninth Gate is Roman Polanski directed Johnny Depp in a movie about a book dealer who is sent to authenticate a rare book that might be able to help summon the devil. It’s… it goes places. And it’s kind of underrated at that. She’s All That is Pygmalion in high school. Another one of those, “Pretty girl we pretend isn’t pretty who gets a makeover that’s basically, “Hey, do your hair differently and take off your glasses” and then surprise, she’s hot! Still, it’s fun. Great cast, looking back on it. Also, remember when Freddie Prinze was a thing?

– – – – – – – – – –



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