My friend Dan emailed me this morning and asked a few of us what the best movie to come out during high school was. While I was thrilled to have a good idea for a blog post, I’ll admit that running through all of the movies that came out in high school made me look like this:
I quickly shot back an email that said I knew “Titanic,” “Shakespeare in Love,” “American Beauty” and “Gladiator” were the four films to win Best Picture while we were in high school, but of course that was just the beginning of the project. I considered “during high school” to mean September 1997 – June 2001, so certain good movies missed the cut-off. I came up with twenty-five good-to-great movies that were my favorites. I omitted guilty pleasures like “Can’t Hardly Wait,” “She’s All That” and “Varsity Blues,” because while I could rewatch them dozens of times, I don’t think they’re the general consensus pick for “best movie.”
I did not use any specific, numerical criteria like IMDB score, Metacritic score, or Rotten Tomatoes review. Instead, I tried to weigh these factors: How good was the movie when I first saw it? How much does it hold up now? How high is its re-watchability? What is its lasting legacy?
In reverse order, the twenty-five best movies from when I was in high school:
25. “The Cider House Rules” (1999): This movie felt like a chore to watch the first time I saw it, but in re-watching it in later years, Tobey Maguire’s performance has grown on me. Still too depressing to watch regularly, but certainly within the realm of “good” movies. Michael Caine’s performance netted him a Best Supporting Actor Oscar.
24. “Being John Malkovich” (1999): I did not get all the fuss over this movie, and I’ll admit I’m still not as taken with it as others. That said, this began the crazy string of Charlie Kaufman/Spike Jonze collaborations that I would come to love. Also gets points for being incredibly inventive.
23. “As Good as It Gets” (1997): What was billed as the tale of Melvin Udall (Jack Nicholson) and Carol (Helen Hunt) ultimately, for me, turns on Greg Kinnear‘s performance as Simon. While earning points for Jack Nicholson and Helen Hunt’s respective Oscar wins, this is another movie I have no desire to rewatch anytime soon. Also loses points for the casting of Skeet Ulrich.
22. “The Fast and the Furious” (2001): With unintentional comedy off the charts, a trailer that popped with the Limp Bizkit song “My Way,” and a five-film legacy, this movie eked its way onto the list. No points for quality, but it more than holds up for re-watchability.
21. “The Talented Mr. Ripley” (2000): I love this movie. I don’t know whether it’s the deception and intrigue that Tom Ripley weaves (especially when he’s pretending to pass himself off as Dickie Greenleaf) or just the fine performances of Matt Damon, Jude Law and Philip Seymour Hoffman. Not the kind of movie I watch frequently, but when it’s on, I’m always captivated.
20. “American Pie” (1999): Another movie that earns points for its legacy, this film launched the careers of Jason Biggs, Chris Klein, Mena Suvari, Tara Reid, Seann William Scott and Shannon Elizabeth. Oh, and, at the time, was the hardest I’ve ever laughed in a movie theater. Bonus points for the blink-182/monkey scene.
19. “Blow” (2001): Just another ho-hum, quality performance by Johnny Depp. I love this period in his career, when he wasn’t Jack Sparrow and was just quietly making great movies. Bonus points for executing the Pablo Escobar/Medellin scenes well before “Entourage” could butcher them. Also the first time I saw Penelope Cruz in a movie.
18. “Super Troopers” (2001): “I don’t want a large Farva.” This movie was like nothing I had seen before. Twelve years later, and I still can’t take a trip to Playa del Carmen without thinking, “You boys like Mexico?”
17. “American Beauty” (1999): I remember being so taken with Conrad Hall’s cinematography the first time I saw this movie. Kevin Spacey wowed me, and I thought Annette Benning’s performance was fierce and hilarious (“I will sell this house today“). Wes Bentley, too, was fantastic, and I thought he and Thora Birch were headed for stardom. But a funny thing happened: I’ve tried on many occasions to watch this again, and I just can’t get through it. We get it: the suburbs aren’t perfect. Other movies have done it better.
16. “Gladiator” (2000): “Braveheart” in Rome, Another Best Picture winner that, upon second or third viewing, becomes more dull and tedious than the Roman times it was depicting. And while Russell Crowe won an Oscar for Best Actor, it was a make-up for his better work in “The Insider” the year before. Bonus points for being the best of a weak Best Picture crop that year (I wasn’t a fan of “Crouching Tiger, Hidden Dragon” or “Traffic,” either). “Are you not entertained?” Maximus shouts at one point. I was.
15. “Rushmore” (1998): Jason Schwartzman’s Max Fischer is one of those characters that you either love or hate. I loved him; his pompousness, his cavalier attitude, and his idealism make him one of the best protagonists of the late 20th century. Bonus points for really launching Wes Anderson’s and Owen Wilson’s careers.
14. “L.A. Confidential” (1997): A simple crime thriller, excellently directed and with just enough suspense to keep you entertained throughout. Major bonus points for using actors who appear repeatedly on this list: Crowe, Spacey, and Guy Pearce. Also holds up incredibly well.
13. “The Sixth Sense” (1999): “I see dead people.” Launched the careers of Haley Joel Osment and M. Night Shyamalan. After the twist ending, it made the movie one you had to re-watch. Sadly, seems to be the peak of Shyamalan’s career.
12. “Shakespeare in Love” (1998): Still one of the biggest upsets in Oscar history, this movie captured Best Picture at the 1999 Oscars. Fine performances by Gwyneth Paltrow and Judi Dench highlight a clever script, and to me the movie is highly rewatchable (though rarely on TV. Get on that, Mark Olsen).
11. “Almost Famous” (2000): I always want to love this movie, but I can’t quite come around and say that it’s excellent. I really enjoy it; the “Tiny Dancer” scene alone is hilarious, and the later scenes with Jimmy Fallon are fun to re-watch. Even Rainn Wilson and the “Rolling Stone” scenes feel really crisp. But while I want Kate Hudson’s performance as Penny Lane to hold up, really I finish this movie thinking about how she, Billy Crudup and Patrick Fugit never really amounted to much (other than her helping the Yankees win the 2009 World Series – thanks, Kate!). Bonus points for high re-watchability.
10. “High Fidelity” (2000): Rob Gordon would probably be offended that a movie about him didn’t make it into the Top 5. Great performances by John Cusack and Jack Black, and a wonderful transposition of Nick Hornby’s book. Simply loses points for having Catherine Zeta-Jones.
9. “The Truman Show” (1998): Maybe the best performance of Jim Carrey’s career, this movie was prescient in its view that the world would be overrun by reality TV. Bonus points for a fantastic performance by Laura Linney, as well as how enjoyable it is on repeat viewings. “And in case I don’t see ya, good afternoon, good evening and good night.”
8. “Memento” (2000): An absolute personal favorite (in my top 5 movies all time), only placed down this low on the list because I don’t think it enjoys the widespread acclaim it deserves. Launched Christopher Nolan’s career, uses incredibly inventive narrative structure, and is one of the most thought-provoking and interesting movies I’ve ever seen. Not the easiest to re-watch, but bonus points awarded to the blu-ray edition for showing the movie in linear fashion as well.
7. “Saving Private Ryan” (1998): The movie that should have won the 1999 Best Picture Oscar. A fantastic performance by Tom Hanks, wonderful direction by Steven Spielberg, and an opening scene that stages the legendary invasion of Normandy better than any movie should be able to, this film is anything but FUBAR.
6. “There’s Something About Mary” (1998): So quotable, and I still can’t think of Brett Favre without referencing this movie. Launched Ben Stiller’s career. Hilarious, and a movie I love to rewatch. Disagree? Step into my office.
5. “Office Space” (1999): So many memorable quotes from this movie that still work their way into everyday use: a jump to conclusions mat, a case of the Mondays, and, above all else, “Office Space”-ing a malfunctioning office machine. So enjoyable on rewatch as well, and packed with jokes. Created the iconic character of Bill Lumbergh.
4. “The Matrix” (1999): One of the only movies on this list that will lose points based upon its disappointing sequels, this movie was revolutionary when it came out. The visual effects, the storytelling (combining Eastern philosophies on nirvana with Western technological fears), this movie had as strong a cultural impact as any I can remember.
3. “The Big Lebowski” (1998): While not #1 on this list, I think the Dude abides. Highly, highly rewatchable, and easily my favorite Jeff Bridges performance (in fact – this might be the one role where he wasn’t performing). Impossible to go to a bowling alley and not drop at least one “Lebowski” line.
2. “Good Will Hunting” (1998): Will, it’s not your fault you weren’t #1 on this list. Launched Ben Affleck’s career, and put him and Matt Damon on the A-list (at least temporarily). Highly rewatchable, and hilarious at parts. Extremely quoteable. One of my favorite movies of all time.
1. “Fight Club” (1999): Lucky for me, the rules of fight club don’t apply and I can talk about how amazing this movie is. Based off of the trippy novel, “Fight Club” has all the attributes of a great movie: a strong cast, led by Brad Pitt and Edward Norton; great action scenes; a twist so sharp that people audibly gasped in my theater; and re-watchabilty that’s off the charts. I can’t not watch this movie whenever it’s on, and to me, it’s only gotten better with time. It can even help if you’re dealing with a bout of insomnia. Bonus points for an amazing soundtrack, and for a great use of the Pixies’ “Where is my Mind?” over the end credits.