Good morning.
We’re back with the next installment of the 40 for 40 series.
As a reminder: This is the series where, because I was turning 40 last year, I decided to pick one movie from every year I’ve been alive if I could only have one movie from that year to watch for the rest of my life.
Since I started doing this, I’ve actually turned 40. But the rules state that the window for this exercise is still open until I legally turn 41. And maybe even 42 depending how long it takes me to get through every year.
If you’re keeping score at home the results so far have been
1985: Back to the Future
1986: The Color of Money
1987: Empire of the Sun
1988: Midnight Run
1989: Indiana Jones and the Last Crusade
1990: Goodfellas
1991: Doc Hollywood
1992: A League of Their Own
1993: Dave
1994: Nobody’s Fool
1995: Babe
1996: That Thing You Do
1997: Grosse Point Blank
1998: The Last Days of Disco
1999: Eyes Wide Shut
Today we do 2000. We’re officially in this century now—depending how you count those things. Let’s get right to it.
As years tend to do, 2000 comes right after 1999, one of the best movie years of all time. It’s not 2000’s fault that it doesn’t have the same highs as 1999! Despite that, it’s still a very strong year that so happens to have two of my all-time favorite movies in it.
Before we get to the shortlist, here are some movies I saw that don’t deserve full entries. Fair warning: Bring it On is not on this list. I have never seen Bring it On. One day I will see Bring it On. But as of right now, I have somehow never managed to see Bring it On.
Movies I saw but not worth full entries
Final Destination. Boggles my mind that this cruel franchise is still raking in dough. Maybe I’m just a humorless bastard but I hate this shit.
Gone in Sixty Seconds. A TBS/TNT weekend afternoon classic. Somehow I’ve seen this movie or part of this movie more than a dozen times. Still very fond of the opening credits. RIP to Robert Duvall who has weird hair in this movie.
Little Nicky. Sandler’s first true sour note since becoming a major star. More would come. This is a bizarre movie.
Me, Myself & Irene. Completely forgotten now, but this movie was a big deal at the time with Jim Carey and peak Rene Zellweger teaming up in a Farrelly Brothers movie. This is Carey’s Nutty Professor and I’m sure it has aged poorly.
Next Friday. The sequel to Friday gave us more John Witherspoon as Craig’s (Ice Cube) dad making jokes about shitting, which is always a good thing.
Reindeer Games. This was the start of Ben Affleck’s wilderness years. But it also introduced us to Charlize Theron.
Ready to Rumble. Little did I know, my passion for professional wrestling was beginning to wane in 2000 even though I was still in a fantasy wrestling league online and hosting matches in my backyard. This movie about David Arquette and Scott Caan tangling with WCW wrestlers was awful.
Scream 3. The end of the original Scream trilogy. I’m still fond of this one because it added a dose of L.A.Confidential into the Scream formula.
The Cell. Shout out to my friend Jeff who was always a fan of this deeply strange Jennifer Lopez vehicle.
The Replacements. Another TNT/TBS weekend afternoon classic. Keanu Reeves playing a washed up quarterback. Gene Hackman playing a legendary coach. Good stuff.
Traffic. Ah, the sprawling turn-of-the-millennium “contemporary issues” drama. I couldn’t even imagine watching this movie today even if it is by Soderbergh and it is astounding that he released this AND Erin Brokovich in the same year.
What Women Want. High concept comedy near the very end of Mel Gibson’s astounding leading man run. This was also the end of Helen Hunt’s brief run at the very top of Hollywood. Both Gibson and Hunt were in FOUR movies in 2000. Crazy.
Now, let’s take a look at the short list.
The Short List
Almost Famous
Best in Show
Cast Away
Chicken Run
Dude, Where’s My Car?
Finding Forrester
Gladiator
High Fidelity
Meet the Parents
Miss Congeniality
O Brother, Where Art Thou?
Remember the Titans
Road Trip
The Perfect Storm
The Ninth Gate
The Whole Nine Yards
Wonder Boys
You Can Count on Me
OK, let’s strike out some movies that definitely aren’t going to be the pick.
The case for Dude, Where’s My Car?: This is a silly, ridiculous stoner movie that isn’t trying to be anything other than that, which makes it good. Even as a teenager, I was prepared to hate this movie—and yet I ended up watching it over a dozen times from 2000-2003. Or at least it felt like that. There is a character named Christie Boner in this movie. But it also gave us the immortal catchphrase “shibby,” which we still use to this day. This is a stupid, well-meaning movie but it’s not the pick.
Speaking of stupid movies. Road Trip. This was a TNT/TBS weekend staple for a long time and I saw parts of this movie so many times on deepening, hungover college afternoons in Upstate New York. Seann William Scott was on a heater coming off his star-making turn as Stiffler in American Pie (1999) and was in both this and our previous entry in 2000. Road Trip is “American Pie but college,” which probably helped give shape to the actual script for American Pie 2 (2001). This is more of a time capsule than a movie: Tom Green, Breckin Meyer, Amy Smart, DJ Qualls! A movie for and of its time, but never to be watched again. Not the pick.
Full disclosure: I fucking love The Ninth Gate. My friends and I watched this movie twice during a sleepover in 2000. This is a weird Roman Polanski movie about the race to find a rare 17th century book in order to use its engravings to open a door to hell. It is a truly wild film noir-ish plot and I honestly can’t explain why I love this movie so much but I do. It’s got a great creepy vibe and several over-the-top scenes that I simply adore. It features Johnny Depp at just about his peak as a leading man and an excellent, menacing Frank Langella playing a character called Boris Balkan. What else do you want?! I’ve seen this movie many times and will always be fond of it, but it can’t be the pick.
In these entries, I often describe a movie as being a “phenomenon” and I’m going to do it a few times in this entry. Maybe it was because the years we’ve been covering were all part of my childhood, but it felt like I grew up in an era of cultural phenomena. And Chicken Run was another one of these. I distinctly remember seeing the four-star review in Newsday and the word of mouth spreading about how good this stop-motion animation movie about chickens was. This movie made over $220 million dollars! And you know what? It holds up! My wife and I watched it a few years ago and it’s still a fun, 84 minute (!!!) romp that’s a riff on The Great Escape (1963). A truly enjoyable watch, but not the pick.
My wife and I watched Newsies (1992) recently. It was the millionth time for me, and the first time for her. I had to admit that it wasn’t very good as a movie to watch as an adult but it got us talking about the heyday of Disney developing family-oriented, live-action movies based around inspiring true stories. This form perhaps reached its peak with Remember the Titans, a movie about a high school football team that must integrate Black and white players in Virginia in 1971. This movie is now well-known for the fact that it is wildly inaccurate, but who could be bothered to look up the facts when you were watching an inspiring story about men learning how to overcome racism and win some football games?! The movie is built around Denzel Washington as the coach of the team. This is right before Training Day (2001) and Denzel might be at the peak of his leading man charisma in this stretch. The rest of the cast is stacked: the always-welcome Will Patton as the defensive coordinator, Wood Harris as a star defensive player, Donald Faison, a young Ryan Gosling, Kate Bosworth, and a very young Hayden Panettiere as a spunky coach’s daughter who knows a ton about football. This is definitely the kind of movie they don’t really make anymore—at least not like this. Another cable staple, I saw this movie or parts of this movie approximately 73 times from 2000-2012. A relic of a different time and certainly not the pick.
Miss Congeniality. This is one of those movies that a lot of people love but that I was never really attached to. I’m not really sure why. My wife and I rewatched this on DVD in a bed and breakfast in Portland, Maine about five years ago and it was a great time! This is Sandra Bullock giving Julia Roberts a run for her money as America’s Sweetheart right before Reese Witherspoon would take the reins after Legally Blonde—but we’ll get to that soon enough. Beloved by many, but not my pick.
“I’ve got nipples, Greg. Can you milk me?” Oh, how we went crazy for this and other iconic lines from Meet the Parents when it came out. Again, this was another phenomenon. This movie made over $330 million on a $55 million budget. I probably rewatched Meet the Parents more than any other movie in the year following its release. It was something you would put on at family gatherings or on just a Friday or Saturday night with your immediate family. That’s because everyone freakin’ loved this movie. They loved seeing Robert De Niro do comedy again and seeing Ben Stiller (as Greg Focker) get treated basically like shit by both his fiancee, Pam aka Pamcake, and his fiancee’s family for an entire movie. This movie is really just one long sit com episode, but somehow it works. I chalk it up to a lot, but Owen Wilson’s performance as Pam’s ex-boyfriend really steals the show and adds so much to the movie when he shows up. Obviously one of the main jokes of this movie, one that the entire movie kind of sets up has aged incredibly poorly. It’s funny that Ben Stiller’s character’s full name is actually Gaylord Focker. Greg is just a nickname. Gay Focker. Get it?! We all ate it up though. Different times, man. A major hit and there are some days I think of putting it on for a trip back to a specific moment in time, but not the pick.
Speaking of specific moments of time, let’s talk about The Whole Nine Yards. This was an ensemble crime comedy that gave Bruce Willis and Matthew Perry pretty equal billing. This was Perry’s last real grasp at leading man fame and came during the peak of Friends’s run at the top of network TV. Bruce Willis was coming off The Sixth Sense in 1999 and was as active as ever—he was in this movie, Disney’s The Kid, and M. Night Shaymalan’s Sixth Sense followup Unbreakable all in 2000. But this movie is maybe more notable for introducing Amanda Peet more widely to audiences and especially to, ahem, teenage boys for a very specific scene. And Natasha Henstridge absolutely glows in this movie. This one was on HBO and cable a lot and so I spent a lot of time with it around 2000-2007. Haven’t watched it in probably over a decade but I imagine it’s still a good time. But it’s not the pick.
“You’re the man now, dog.” Anyone of a certain age understands how important that sentence is. That, of course, is the immortal line that the author William Forrester, played by Sean Connerey, utters to Rob Brown’s Jamal Wallace in Finding Forrester. That quote was all over the trailer for this movie, which was on TV a lot. This movie finds Gus Van Sant getting back into his Good Will Hunting (1997) bag after he directed the 1998 remake of Psycho. Here, instead of a haunted widower therapist helping a working class white kid in Boston, we have a reclusive novelist helping a kid from the Bronx navigate prep school and realize his potential as a writer. This movie features both writing and basketball as its protagonists two interests so naturally I was obsessed with this movie for many years. A solid, inspirational movie that brings up fond memories but I haven’t longed to watch Finding Forrester in some time. Not the pick.
But Finding Forrester wasn’t the only movie about a literary young man that came out in 2000. No, there was also Wonder Boys, the adaptation of Michael Chabon’s 1995 novel of the same name, which was a follow-up to his successful debut The Mysteries of Pittsburgh (1988) which is one of the great summertime/coming-of-age books ever written. I love this movie and always have. I mean, c’mon. I was a freaking English major who went to a small liberal arts college in Upstate New York and spent most of his time brooding over short stories he was writing. This book and this movie were MADE for me. My wife and I did a rewatch of this a few years ago and it is admittedly a bit shaggier than I remembered but there is so much to recommend: Michael Douglas playing expertly against type as a dishevelled writing professor and flailing novelist, a young Toby Maguire being weird and enigmatic, Robert Downey Jr. showing signs of life on his long road back to the top of Hollywood and doing his brand of effortless charm while also being sort of sleazy, Frances MacDormand being solid as usual and hitting some of the same notes she hits in another major performance from this year that we’ll be covering soon, Rip Torn as Michael Douglas’s character’s rival, and Katie Holmes is also in this movie and acting. Now that I look at it, that is a very 2000 cast. I’d put this movie on anytime, but somehow it’s not the pick.
I saw The Perfect Storm in theaters when it came out because, well, you had to. This was a major drama starring George Clooney and Mark Wahlberg (both about to cement themselves as major A-listers) in which they go up against THE PERFECT STORM. What? Was I not going to see this in a theater? And I remember liking it but it didn’t really leave an impression on me. And, honestly, aside from catching a few snatches on cable over the years (this was a MAJOR cable movie) I didn’t really ever think about it for over twenty years. But for some reason around the holidays in 2024 heading in 2025 I caught this movie in its entirety and in very large chunks several times at my parents house in Long Island. And you know what? This movie is GOOD. Sure, it’s a melodramatic story of a doomed fishing crew that’s based on a true story but you’re gonna hold that against it? Really? When it features an insane cast of character actors such as Wlliam “There’s a dead man on the other end of this phone” Fichtner, John Hawkes, the immortal Karren Allen, the absolute legend Mary Elizabeth Mastrantonio, and John C. Freaking Reilly. Oh, and it also has Diane Lane working really hard to land the coastal Massachusetts accent. There is entertainment in every scene. This movie is why movies were invented. Worth a revisit—and, yet, it’s not the pick.
Here’s that word again: Best in Show was another “phenomenon” from 2000. I remember being at my friend Chris’s house and him asking me if I’d seen Best in Show. I shook my head and then we proceeded to watch it alongside his parents. After that, it seemed as if every other week someone was talking about the movie. The movie only made $20 million at the box office (on a $10 million budget) but this was a movie that everyone seemed to have on DVD. It was brought up in conversation all the time. I mentioned that Meet the Parents was a movie you’d put on to please a family crowd—well Best in Show was also that. There was a character or a bit for everyone to laugh at. The thing is, I stopped returning to this movie probably around 2005 or 2006. As I mentioned in the 1997 entry, I haven’t watched the Christopher Guest movies in a long, long time and that probably says something. A major comedy touchstone of its time, but not the pick.
Am I really going to talk about Gladiator? I guess I have to. You don’t really need to tell me about Gladiator. This movie has such a huge reputation that is kind of outsized for what it actually is—a perfectly fine sword and sandal pic. It’s probably more notable for how the opening battle spurred on my interest in history around the Late Antiquity and Early Medieval periods. Who actually were those people the Romans were fighting out there in the snow in the woods? What’s their story? I mean this is Gladiator. I’m not going to pick this as the movie from 2000 because I couldn’t imagine watching this movie every day. My wife and I barely made it through a rewatch last year. At least it isn’t Gladiator 2. Not the pick.
I’m coming fresh off a rewatch of O, Brother Where Art Thou?, so I can safely say that this is actually kind of a minor work in the Coen Brother’s filmography at this point. But, again, at the time, this movie was an absolute phenomenon. Or, rather, the soundtrack was the real phenomenon. Like, it would have been strange in 2000-2003 if you weren’t listening to the O, Brother Where Art Thou? Soundtrack in your car at some point. It honestly feels crazy to think about it that way, but it’s true. As a movie, it’s completely fine. It looks amazing and Clooney, Turturro, and especially Tim Blake Nelson are doing fantastic face acting throughout the film. I’m a sucker for episodic stories with some tie to the The Odyssey (800 BCE) but I found myself sort of drifting in interest during the latest rewatch. Though, I will say this movie’s version of the “I guess everything worked out” type of ending is masterful. The truly exceptional thing about this movie? Charles Durning’s performance. Otherworldly comedic timing and delivery from a legend. Could anyone else do what he does in Tootsie (1982), Home for the Holidays (1995), and this movie and then also do what he does in a movie like Dog Day Afternoon (1975)? Maayybe. But it’s definitely a short list. Solid film with a truly iconic soundtrack but it’s not the pick.
That was actually harder than I thought! But that leaves us with a very strong final four.
The Final Four
Almost Famous
High Fidelity
Cast Away
You Can Count on Me
Let’s start with High Fidelity. Well, OK. So some of the gender politics in this movie are problematic today. The main character’s (Rob’s) approach to his past relationships is also adolescent at best. And, sure, the main reveal in the movie is that Rob cheated on his girlfriend while she was pregnant—but he didn’t know! That’s all true, but this movie is still completely rewatchable. It’s probably not surprising that a guy like me who makes monthly playlists and writes thousands of words about the songs on them likes this movie, which features a record store owner making mixtapes and talking about music with his friends/coworkers. There’s a ton to like about this movie and they recently did a good Rewatchables episode about it if you want to go deeper. But you probably already know why High Fidelity is a fun watch. It has John Cusack at perhaps his Cusackiest—though I’d argue 1997’s pick, Grosse Point Blank, is the culmination of the screen presence he built steadily over the previous ten plus years. There’s great bit parts for Catherine Zeta Jones and Lily Taylor as two of Rob’s exes. Tim Robbins gets to play a great creep. And Jack Black fucking steals the show as one of Rob’s record store employees, Barry. If you watch this movie as a sort of passing of the torch of Cusack as a leading man to Jack Black as a soon to be dominant force at the box office it becomes even a little more interesting. As easy to watch as this movie is, and despite all the times I’ve watched it it’s never become one of my all-time favorites. I don’t have an irrational attachment to it. So, because of that, it can’t be the pick.
If you asked me, “Matt, in your lifetime what were the two movies that played the most on TNT and TBS?” I would probably answer “Shawshank Redemption (1994)…although that was on USA and AMC a lot and maybe not as much on TNT and TBS. And Cast Away. That was definitely on TNT and TBS all the time.” I couldn’t hazard a guess at how many times I’ve seen Cast Away. And no matter how many times I have watched it, it always sucks me back in. This movie marks the end of Tom Hanks’s incredible peak as perhaps the movie star of the 1990s. And what a way to go out! A movie that he carries for basically the entire second act by himself. You don’t need me to tell you about Cast Away. Chances are you’ve seen it a million times too. You’ve cried like I have when Wilson the volleyball floats away from the raft just before Chuck gets rescued by the container ship and have thought to yourself, “God damn I just got choked up over a volleyball ‘dying’ again!” It’s funny, Cast Away in fact marks a series of endings. As I mentioned earlier, this was one of four movies Helen Hunt was in this year and yet Cast Away ended up being the last of her truly noteworthy leading performances. This also is the end of Robert Zemeckis as a great director. Yes, Flight is an outlier in 2012, but Zemeckis was really never the same after this movie. This is his filmography from 1984-2000: Romancing the Stone (1984), Back to the Future (1985), Who Framed Roger Rabbit (1988), Back to the Future II (1989), Back to the Future III (1990), Death Becomes Her (1992), Forrest Gump (1994), Contact (1997), What Lies Beneath (2000), and Cast Away (2000). I mean…was there another director who had a hand in delivering more movies that defined the fabric of pop culture during that time? Probably only Spielberg. But after 2000 we get The Polar Express (2004), Beowulf (2007), A Christmas Carol (2009), Flight (2012), The Walk (2014), Allied (2016), Welcome to Marwen (2018), The Witches (2020), Pinocchio (2022), and Here (2024). It’s like you can almost see the cliff he fell off. And I don’t say that mockingly. It would be impossible to continue the run of work he’d created for over 15 years. It’s just the drop off comes fast and steep. Kind of like that cliff Chuck considered hanging himself from in Cast Away. A beloved and fascinating movie to this day. But not the pick.
The first time I saw You Can Count on Me was in April of 2024 when I had the flu. For some reason, I decided to dive into the work of Kenneth Lonergan while I was sick so I rewatched Manchester by the Sea (2016) and watched his other movies for the first time. Since then, I have rewatched this movie four times and think it is one of my favorite films ever. I wrote about it back in 2024 and here’s what I said then:
“You Can Count on Me is sick. This movie should be talked about more as one of the best films of the past 30 years. This movie has Laura Linney doing amazing things as a lead actress. This movie has Mark Ruffalo being like so many guys you’ve known. This movie makes you feel like you’re living in Upstate New York no matter where you’re watching the movie. That’s because this movie, like Manchester By the Sea, is made by Kenneth Lonergan and Kenneth Lonergan understands that part of what makes a movie great is that it takes place somewhere.”
I don’t really have much to add. It’s a heartbreaking but life-affirming movie that is absolutely true in so many ways. We should be having conversations about it with each other actively every week and yet we don’t. And that’s a real shame. I could watch this movie every day and never get bored. And yet, it’s not the pick.
No, that would be Almost Famous.
If it’s not clear to you by now, my brain has long been warped by classic rock radio, music journalism from the 1970s, rock documentaries, and the established canon of “rock” music. The side effects of which you can read more about in Steven Hyden’s Twilight of the Gods (2018).
And the year all of this started was 2000. That’s when I was gifted Early Days: The Best of Led Zeppelin (1999) and Different Times: Lou Reed in the 70s (1996) by my parents for my 15th birthday. From there, I started to explore their dusty collection of vinyls and resuscitated our unused record player. I started listening to 102.3 and 104.3 whenever we were in the car. I started wearing tie-dye t-shirts and going to Allman Brothers concerts. And in the spring of 2001, I watched Almost Famous for the first time in the basement at my friend’s girlfriend’s house. That spring I must have watched it a dozen times. It made me go out and buy Psychotic Reactions and Carburetor Dung (1987), the major collection of Lester Bangs’s music criticism from the 1960s up until his death in 1982. I started writing Lester Bangs inspired rants and raves about music and life and being a lovesick loser in my journals.
I still recall Memorial Day 2001. In my town on Long Island, Memorial Day was always a big deal. There was a parade that went down our main street and when I was in high school people always got together to hang out or have a daytime party somewhere. In 2001, I had people over at my house. At some point, we put on Almost Famous. Then, later in the afternoon, after people had drifted home. I remember walking along the road with one of my best friends. I don’t know where we were walking to or why. But we talked about life and girls and whatever the hell else you talk about when you’re 15 years old. At some point we parted ways. It was a beautiful May afternoon and I was alone with my Discman and one of the Led Zeppelin BBC Sessions (1997) CDs. I remember listening to “That’s The Way” and thinking about how it played in Almost Famous. That sounds unremarkable but it has stuck with me, I think, because it was one of those rare moments in your teenage years where you are aware for a moment that you are alive—you’re not just living. You are alive and aware that something is happening. You’re getting older. Something in you is changing, but you can’t even start to express what it is.
In so many ways, I inherited and was gifted the pop culture of my parents. And I’m thankful for that even though it does sort of worry me in a way—that I’ve spent so much time celebrating old things in my life instead of new things. Almost Famous is in so many ways the manifestation of that inheritance, of that gift. It’s a classic story in the Joseph Campbell mode: our hero leaves his home and enters a new world—he goes from obscurity to notoriety. In this case, it’s the thinly veiled story of Cameron Crowe’s life as a music journalist for Rolling Stone in the 1970s.
This movie has so many remarkable things about it. Stillwater actually feels like some band from the early 1970s that might break it big. Billy Crudup and Jason Lee could be rock stars that were lost to time. Everything about the period the movie takes place in seems like it actually happened.
The more I watch this movie, the more I think Frances McDormand’s role as William Miller’s mother is the key to the movie. When you watch it as a young person, you sort of see her as, if not a villain, then just a road block on this fun journey through the rock and roll world of the 1970s. But as you get older you think about how hard that would’ve been as a parent, how strange it would have been to raise a child during this time when so much of contemporary life seemed to be changing fast. And her beliefs are actually kind of liberal! She’s not some conservative parent afraid of change. She’s just worried about her son. I actually think it’s one of McDormand’s best performances and one of Crowe’s best characters.
I often put on Almost Famous when I’m looking for comfort. But it always leaves me with a sort of melancholy feeling. I never experienced the world it depicts, but that world looms so large over my understanding of time and history and pop culture. That world has, for better and for worse, defined so much of my interests and how much I’ve spent my time. It makes me long for that time even if longing for any time you didn’t live in is incredibly foolish . And it also makes me sad to think that time, which I didn’t live in, and the culture that was created within it will continue to fall out of relevance—more and more of the music and the cultural touch points will become relics, lost and forgotten as time marches on. It also reminds me that my parents are getting older, because that was the time of their youth and they instilled an appreciation in me for the things that they loved when they were young.
But at the same time, it also makes me miss the time when I was 15. When I was just discovering this movie and discovering what made me come alive to the world. That time, the way life was then, is fast disappearing too. Almost Famous has the power to make me both miss my own youth, as it continues to further recede in the rear view mirror, and my parent’s youth, which I had no part of.
I can’t think of any other movie that makes me feel that way. And every time “Feel Flows” by the Beach Boys plays over the ending credits, I both feel satisfied and hurt a little bit. And I want to watch it again.
That’s why it’s the pick.