Best Movie of the 2000s Update #1: The First Batch
It’s 2000s time, baby!!! We’ve got Razr phones. We’ve got Razor scooters. T9 texting. AIM screen names. Those weird bubble shirts that looked doll size but stretched out like crazy and were sold at Walmart for like four dollars. Many of these movies in this set were watched as we Amtrak’d across this beautiful US of A. We are so pumped to start this all over again with a brand new decade. Y2K dude!
Almost Famous (2000)
Tom: I hadn’t seen this before. It was less raunchy than expected actually - but it was a cool coming-of-age story with a special performance from Kate Hudson. Cameron Crowe says it was written based on his experiences writing for Rolling Stone as a teenager in the 1970s, and there is barely a single drug taken by any rock band?! C’mon. But it’s super entertaining and one that I’ll definitely revisit if I catch it on TV.
Erin: I originally watched this in early high school and felt very ***rebellious*** because it was RATED R. Now that I’m much closer to AARP vibes…this felt super sanitized, like, if Woodstock was at Lego Land or something. Still, Kate Hudson is awesome in it, and the soundtrack is bop after bop. And I like to say “it’s all happening!” to this day, even if it’s usually a reference to Scheana’s tattoo from Vanderpump Rules.
Save the Last Dance (2001)
Tom: Okay I thought this movie was going to be horrible - and it was - but it was super entertaining and didn’t culturally appropriate nearly as much as I thought it would. The fact that they spelled “Juilliard” wrong on a sign in one scene in a movie about making it into Juilliard is absolutely incredible.
Erin: I NEVER WATCHED THIS!!! Let me just say, I was obsessed. The story held up surprisingly well, Kerry Washington was clearly a star in the making, and Julia Stiles was such a horrific dancer. Truly iconic and unhinged behavior.
Adaptation (2002)
Tom: This movie blew my mind to pieces. It’s Nic Cage as weird neurotic twins, Meryl Streep in a role you haven’t really seen her in before, and Oscar winner Chris Cooper in a movie about a writer struggling with writer’s block to write a screenplay. That sentence can’t even come remotely close to capturing the essence of what is truly an unhinged film. I can’t even get into how off-the-wall this movie is. I loved it. If you are into mind-bending stuff you should definitely check it out.
Erin: This is a film that hurts your brain in the way that you totally understand it but can’t comprehend how a human mind conceived it without melting. Anyone who says that Nicholas Cage is a bad actor is WRONG AND YOU SHOULD NOT BE THEIR FRIEND. Or, you should at least watch Adaptation with them first, arms crossed, with a “see???” smirk on your face the whole time.
Chicago (2002)
Tom: Can John C. Reilly ever play a husband who isn’t completely emasculated? #JusticeForJohnC. I really liked Chicago - it had a much more interesting storyline than I anticipated, and Renee Zellweger killed it. I’m not a major musical fan, but I liked that this one explored compelling ideas of jealousy and hypocrisy in the justice system using a surrealist fantasy lens. The part where Roxie (Zellweger) mutters “Jesus, Mary, and Joseph” and prison guard Matron Mama Morton (Queen Latifah) responds “You’re talking to the wrong people” truly cracked me up.
Erin: Loved this then, love it even more now. My very religious piano teacher (who now allegedly loves conspiracy theories and posts about them on Facebook???) recommended this to me. Now looking back…that was so beyond inappropriate. I STOPPED piano lessons in 8th grade. STOPPED. So I was like, eleven or something!!!
Minority Report (2002)
Tom: Spielberg got a little weird around this time - after Saving Private Ryan, he went with two sci-fi films: this one and A.I.: Artificial Intelligence. But this one, based on the Philip K. Dick novella of the same name, is a compelling mix of sci-fi, noir, thriller, and mystery, and it really works! Colin Farrell and Max von Sydow are excellent, and as much as I hate to say it, Tom Cruise is incredible too.
Erin: This movie made me go, “whoaaaaaa” through most of it. We also watched it in a little bus on the way to Yellowstone and this really creepy guy who was like if Sam Elliot smoked like five packs of cigarettes an hour was behind us and was yelling a lot on the bus. So that took me out of the movie for the last half an hour ugh.
Sideways (2004)
Tom: Alexander Payne is such a gifted filmmaker: he took a movie about two unlikeable, selfish friends (a self-pitying Paul Giamatti and an adulterous Thomas Haden Church) on a road trip to California wine country and turned it into a funny, emotional film buoyed by Virginia Madsen and an unhinged Sandra Oh. Love me some Giamatti and THC though. This is a really good movie.
Erin: Wine sales went through the roof when this film came out, and I find it truly fascinating that it really was a big hit. Don’t get me wrong, it was an excellent movie—funny, thoughtful, character-driven, with some of the best performances I’ve seen in the 2000s. But seriously, it’s a sad movie disguised as a comedy about California wine that doesn’t even take place in Napa or Sonoma. All of the Gen X and older people I’ve talked to have seen it and always say, “is that the movie that takes place in Napa?” So maybe it’s like a Mandela effect thing?
Capote (2005)
Tom: Philip Seymour Hoffman is a god. He won best actor for his role as Truman Capote as he researched and wrote the seminal true crime novel In Cold Blood (which is fantastic) and he’s just so…smarmy and arrogant, but eminently likeable. If you’re into true crime at all, definitely watch this. And Catherine Keener plays Capote’s good friend Harper Lee! That’s cool!
Erin: I mean, OBVIOUSLY Philip Seymour Hoffman is God-tier in this. And I found the storyline fascinating because I really enjoyed In Cold Blood. I did find the movie a bit meandering, though. A tighter screenplay would have made it more of a slam dunk for me.
The Squid and the Whale (2005)
Tom: I am on record as feeling that Noah Baumbach’s latest movie about divorce (likely his own divorce from Jennifer Jason Leigh), Marriage Story, is flat and bad. The Squid and the Whale, about a divorce (Baumbach’s parents’ divorce) from the perspective of the children (Jesse Eisenberg and Owen Kline), landed much better with me. It’s complex and subtle, and Jeff Daniels and Laura Linney truly act as if they are at the end of a decaying relationship, even giving you glimpses into what was likely the “good times.” I liked this one a lot.
Erin: Jeff Daniels’ character is SO well written. I really really enjoyed watching how his narcissistic yet painfully insecure insufferable-ness affected his family. It was also SO MUCH BETTER than Marriage Story and I didn’t go 😬 because it was cringey when Adam Driver punched the wall.
Hot Rod (2007)
Tom: Andy Samberg forever. Hot Rod isn’t quite Popstar, in my opinion, but there’s some classic Lonely Island stuff in here, including the part towards the end where they are marching through town and people start following them and singing and then the entire thing turns into a riot and the town gets destroyed. For no reason. Another great part is when Rod falls down a steep hill for like 15 minutes. And his rivalry with his stepdad (Ian McShane) is hilarious.
Erin: Hot Rod isn’t as consistent as Popstar (but then again, what is?). The highlights, however, are as airborne as Rod’s bike ramps and dreams. Immediately after watching the movie, I YouTubed the endless fall through the forest scene and watched it over and over.
Burn After Reading (2008)
Tom: I’ll tell you what - the first two-thirds of this movie are great. It’s all these famous actors playing ironic twists on their usual typecasts - George Clooney is a handsome U.S. Marshal but he’s paranoid and a cheater, Frances McDormand is sexually awakened, but very vain, Tilda Swinton is hot but a horrible person, John Malkovich is the straight man, and Brad Pitt is…just iconic. I thought the third act didn’t quite live up to the first two, but it was an entertaining Coen Brothers output nonetheless.
Erin: This movie absolutely falls apart and I was left feeling like…what? Why did I watch this? And then I remembered: Brad Pitt as Chad. And I felt whole again.
Tropic Thunder (2008)
Tom: Okay, so the hot topic from this is that Robert Downey Jr. would never be able to play his role in this movie if it were made today. I’m not sure about that, thanks to the power of satire, but Ben Stiller plays Simple Jack so earnestly that that might need a bit of a change. And the portrayal of the Vietnamese people. But overall, the movie’s still hilarious and the humor more or less holds up.
Erin: I really think everyone my age saw this movie in high school. It was such a sensation! Weirdly, teens find this movie every few years and feign outrage on Twitter, which is kind of genius and almost proves one of the themes of the film, which is using controversy to stay relevant and intriguing to the industry.