On December 30, 2025, The Ringer podcast dropped an episode of The Rewatchables that wasn’t covering a single movie but instead was host Bill Simmons personal Top 50 Rewatchable Movies of the 21st Century.

By making the list about the 21st Century it means the century begins not in 2000 but January 1 2001.

I… can’t do that.

Of course my mind raced about doing my own list on this but I couldn’t do 21st Century. That cuts out 2000, which means I’d be cutting out my number one on the list. So I have to word it differently if I’m going to do this list.

Top 25 Movies since I turned 15? Nah.

Top 25 Movies since I went to high school? Eh.

Top 25 Movies since 2000? Good enough.

The idea of a rewatchable of course doesn’t necessarily mean it’s the best movie, but it does often mean best movie too. You’re going to rewatch the movie you love the most. I decided to weigh every entry with six points:

Full Watch: How many times have I watched the movie in full

Clip Watch: How many times have I watched clips of the movie on YouTube

Rent Free: How many times have I quoted or thought about it when not watching it

Film Love: How much I love the movie

Film Importance: How important the movie was to me at any time in my life

Recommendation: How many times I have suggested the movie for someone to watch it

I’ll go low/mid/high for each of these. The top three movies are a high on all categories.

25. Sinners

Full Watch: Mid
Clip Watch: Low
Rent Free: High
Film Love: High
Film Importance: Low
Recommendation: High

Sinners is certainly the newest movie to make this list, as I called it my favourite film of 2025. I’ve already watched it a few times and thought a lot about it in just a few months. I actually haven’t watched a lot of clips back on it surprisingly, though that could be due to how new it is.

I think it’ll end up lasting for me just due to how tight I think it all was. It’s beautiful to watch, wonderful performances, and it scratches an itch I’ve always wanted scratched. No, not vampires. Mafiascum/Werewolves. I absolutely love playing that game, either in person or videogame versions like Town of Salem. I once ran a big message board version once and it was a lot of fun creating the story. I love that sort of Thing style “who is the intruder” and I think Sinners handles it better than almost any other movie I’ve watched. The Thing might be the only one better. The advantage on Sinners? It makes me feel for the intruders/invaders unlike The Thing. I have no emotional attachment to an alien like that. An Irish vampire wanting everyone to be together with no discrimination? Assimilation? I can empathize with that.

24. The Grand Budapest Hotel

Full Watch: Mid
Clip Watch: Mid
Rent Free: Low
Film Love: High
Film Importance: Low
Recommendation: High

I’ve recommended Grand Budapest Hotel as my favourite film from Wes Andersen in the past, and it’s a big reason why it ends up on the list. I think it’s a brilliant film that incorporates multiple characters and comedy in a great way. It’s also one of my favourite visual films.

23. Creed

Full Watch: Mid
Clip Watch: High
Rent Free: Mid
Film Love: High
Film Importance: Low
Recommendation: Mid

I only have two sports movies on my Top 25 and the other one is more about the philosophy than the actual sport itself. Walking out of Creed in theatre I came out feeling it was superior to the Rocky films and one of the best sports movies I ever watched. I still watch clips for inspiration when I need it at the gym. It’s just a really well made movie that happens to be about boxing.

22. The Cornetto Trilogy

Full Watch: Mid
Clip Watch: High
Rent Free: Low
Film Love: High
Film Importance: Mid
Recommendation: High

Yes, this is cheating. I should have to settle for one of the films. Shaun of The Dead, Hot Fuzz, or The Worlds End. I was originally going to go with Hot Fuzz and then I forgot this is my own list and fuck you. I think they all contain their own importance and why they end up rewatched. Shaun of the Dead is so quick and fresh even in rewatches. Hot Fuzz is a great send up of the buddy cop genre with Timothy Dalton as one of my favourite villains ever. The Worlds End is a beautiful film about struggling to grow up and let go of your past, and something I can relate to. Also Rosamund Pike is so beautiful.

21. Wet Hot American Summer

Full Watch: Mid
Clip Watch: High
Rent Free: Mid
Film Love: Low
Film Importance: Low
Recommendation: High

One of my favourite comedies of the 2000s that got me into projects from other people in the cast. I definitely watched Party Down and Burning Love due to Ken Marino adopted Paul Rudd as a spirit animal due to this movie. I love how it sends up the 80s teen movie genre which I’ve always been obsessed with. It may seem like I’m not that high on it but the clip watches are very high.

20. In Bruges

Full Watch: Mid
Clip Watch: Mid
Rent Free: Mid
Film Love: High
Film Importance: Mid
Recommendation: High

I originally had In Bruges higher but then realized it should be a bit lower on the list. Incredibly funny movie, great story, runs very similar to a Shane Black movie so it’s no surprise I love it so much. Colin Farrell around this time had a pretty boy reputation with me and I wasn’t too high on him but this movie changed my perspective on him. Since I’ve considered him one of my favourite actors. Also great representation of Canadians.

19. American Gangster

Full Watch: Mid
Clip Watch: High
Rent Free: High
Film Love: Mid
Film Importance: Low
Recommendation: High

I kept wondering where I should rank American Gangster. I’m higher on it than most are, and think it’s one of Ridley Scott’s best. Most would have a Denzel Washington movie like Training Day over American Gangster, but the performance of Russell Crowe in this helps push it on the list. The scene where Denzel and Russell sit down and negotiate is one of my favourite scenes in any movie. I think it’s one of the best actor versus actor scenes I’ve ever seen, the way how one man unwavers and the other runs through his emotions and thought process.

18. Hell or High Water

Full Watch: Low
Clip Watch: High
Rent Free: High
Film Love: High
Film Importance: Low
Recommendation: High

“YOU’D THINK THERE’D BE TEN OF ME!”

I watched that scene like 100 times before I saw the movie. I didn’t know what the movie would end up being. It ended up one of the best neo westerns I’ve ever watched and made me a forever fan of Ben Foster. It’s so well shot and so well carried. I can’t believe Taylor Sheridan did this and another movie on my list then makes so much crap now. I guess that’s what happens when you go from having to refine a single script to making multiple episodes of old guys acting like tough guys. People usually separate neo westerns from traditional westerns but I like High or High Water more than any traditional western.

17. John Wick

Full Watch: Mid
Clip Watch: High
Rent Free: Mid
Film Love: Mid
Film Importance: Mid
Recommendation: High

I considered doing what I did with the Cornetto Trilogy and listing all of the John Wick series but the reality is that the sequels lose their value after the first watch. Some characters do interesting stuff and there are good scenes to rewatch but nothing holds up like the original John Wick. The only problem with the original John Wick was using so much Marilyn Manson for the score. Everything else is such a tight rewatchable package. I have specifically watched the whole, “They call him the Baba Yaga” scene in clips so many times, I’ve watched it more times than I watched any of the sequels combined.

16. The Social Network

Full Watch: Mid
Clip Watch: High
Rent Free: Mid
Film Love: High
Film Importance: High
Recommendation: Mid

I really fought with myself whether it should be The Social Network or Gone Girl. Gone Girl absolutely could have made this list. I’ve thought about it, I love it, I’ve recommended it, but I had to be honest with myself. How many times have I clip watched it? It isn’t much. This is an example of where I’d say Gone Girl is a film I like more, but The Social Network is far more rewatchable.

I remember seeing it opening night in a packed theatre in Kingston, Ontario and I think a lot of people like me went in wondering why David Fincher, director of Fight Club, was making a movie about Facebook. It really isn’t a Facebook film, but a movie about the obsession of belonging. David Fincher’s career is all about examining those who get so obsessed about something it takes over their life. Or at least his best films. It doesn’t hurt you have Aaron Sorkin ensuring the talking is slick as hell, and the score by Trent Reznor and Atticus Ross essentially changed film scoring in the 21st century.

15. Sicario

Full Watch: Mid
Clip Watch: High
Rent Free: High
Film Love: High
Film Importance: Mid
Recommendation: High

I saw Sicario before I watched Hell or High Water and Sicario is one of those films I’ll talk about any day. It’s not even really about the plot, though I’ll fight anyone who tries to push that, “Kate is the real villain” shit when THE UNITED STATES OF AMERICA is obviously the villain of the movie. It’s about individual performances and the way it all comes together. There’s a claustrophobia of the film in how much you don’t know and how much fear that can create. I think I’ve watched every Benicio del Toro scene from the water cooler to the confrontation with the family so many times it makes me sometimes forget about the rest of the movie.

14. Scott Pilgrim vs. The World

Full Watch: High
Clip Watch: High
Rent Free: Mid
Film Love: Mid
Film Importance: High
Recommendation: High

The other day I found myself rewatching the scene where he fights the Vegan. I don’t even remember why but I pulled it up. While I said it’s mid for rent free there’s one reason it’s high in the rent space: Mary Elizabeth Winstead. This film led to my obsession with her. I’m certainly not the only guy to say that I’m sure. It’s also a great Canadian movie. I had to bump out Blackberry from this list when I wanted it on as a great Canadian rewatchable but we still have Scott Pilgrim to remind us what Toronto used to look like. You know, before the Ford’s ruined it.

13. Mad Max: Fury Road

Full Watch: High
Clip Watch: Mid
Rent Free: Mid
Film Love: High
Film Importance: High
Recommendation: High

I love reminding people how simple Mad Max: Fury Road is. They literally go one way then go back. That’s it. When you think you need something complicated and intricate and goes in several places? Think about Mad Max: Fury Road. It leaves a bit of a bad taste in my mouth that Charlize Theron never got to play Furiosa again but this is still one of the best action movies ever made.

12. The Departed

Full Watch: High
Clip Watch: High
Rent Free: High
Film Love: High
Film Importance: Mid
Recommendation: Mid

THE DEPAHHHTED. Honestly, I should have mentioned it back when talking about Sinners and Mafiascum/Werewolves type movies. The Departed might be the start of that for me. The two guys on each side of the law pretending to be something they are not. It’s a movie all about authenticity and Marty Scorsese deserves all the love in the world for leaving open questions and fighting the urge to answer everything for the viewer. That’s what makes you want to talk about it.

11. Michael Clayton

Full Watch: High
Clip Watch: Mid
Rent Free: Mid
Film Love: High
Film Importance: High
Recommendation: High

Whenever people talk about how great the year 2007 was I make sure Michael Clayton is brought up. There’s so many great concepts in it. Everything from a fixer who can’t fix his own life, a litigator losing his sanity and having to be put down, and a general counsel in over her head trying to survive as a woman in a high stakes corporate world making decisions based on survival that eventually ensnare her. Roger Ebert talked about how he didn’t know the vast significance it would have on society but felt it perfect as an exercise of the genre. That Rog knew a thing or two about talkin’ pictures. It also has what I still feel is the best killing in any movie. Clean killing. Make it look like a suicide. The whole process they do that is just brilliant.

10. Kiss Kiss Bang Bang

Full Watch: High
Clip Watch: High
Rent Free: Mid
Film Love: High
Film Importance: Mid
Recommendation: High

I used to have Kiss Kiss Bang Bang as my ritual Christmas movie. It’s only not due to a different Shane Black movie. Shane Black makes movies that my head loves. He hits so many of the elements I love. Everything from the schlock detective novels to the characters in their 30s feeling like life is finally passing them by. Screw ups who screw up the right way and competent investigators having to deal with idiots.

09. The Raid: Redemption

Full Watch: High
Clip Watch: High
Rent Free: Mid
Film Love: High
Film Importance: Mid
Recommendation: High

I consider both Raid films to be the best martial arts movies I’ve ever watched. I have watched the clips so many times on them and I’ve watched both several times. I could have combined them but I didn’t for reasons I’ll get into. I’ve recommended The Raid more times than almost any movie. As a film itself it’s… you know it’s fine. It’s not great but it’s easy to follow and handles a self contained story well. It’s funny that Dredd got made around the same time also stuck in one apartment complex. More movies should just keep budgets low by doing that.

08. Moneyball

Full Watch: Mid
Clip Watch: High
Rent Free: High
Film Love: Mid
Film Importance: High
Recommendation: High

I almost forgot Moneyball from this list which would probably make you think it shouldn’t rank high on Rent Free but like a lot of other men who watch sports? I’m always thinking about Moneyball. I’m always wondering if the way things are being done in sports (or anything really) is the right way to go. Is there a better way we’re not using? I know I’ve always thought about that but never the way Moneyball jogs my brain. I’ve probably watched clips on it on YouTube more than any other movie. The movie itself is good, not great, and the subplot about Brad Pitt’s daughter screeches the film to a halt every time it pops up. But as a clip movie? It’s unrivaled.

07. Superbad

Full Watch: High
Clip Watch: High
Rent Free: Mid
Film Love: High
Film Importance: High
Recommendation: High

Superbad is the perfect teen movie for my generation. It came out in 2007 which means I was out of high school by the time it came out but not that far out. I finished high school in 2004. Oh yeah, ANOTHER 2007 MOVIE WHICH NEEDS TO BE MENTIONED MORE! My love of redheads started prior to Emma Stone, but Emma Stone might be the perfect one for actors. To this day even. She’s the perfect high school crush in this. Jonah Hill and Michael Cera actually act like they could have been friends of mine in high school. It’s extremely funny, very relatable, and the scene where Hill talks about constantly drawing dicks always kills me.

06. High Fidelity

Full Watch: High
Clip Watch: High
Rent Free: High
Film Love: High
Film Importance: High
Recommendation: Mid

Like many men my age or older I wanted to be John Cusack. Not the actor, no, but the characters he plays. You go from The Sure Thing, Better Off Dead, and his cameo in Stand By Me. You top it off with Say Anything. That’s the guy you want to be when you’re younger. Then you get a little older and you want to be Grosse Point Blank, The Grifters, but especially High Fidelity. Later you really just got Hot Tub Time Machine, which is a guy getting his chance to be those guys again. But High Fidelity was everything to me as a teenager. The troubles with girlfriends, the obsession with music and pop culture? He was likely a bad influence, but still a primary influence.

05. Lost in Translation

Full Watch: High
Clip Watch: Mid
Rent Free: High
Film Love: High
Film Importance: High
Recommendation: High

Lost in Translation is why I still dream of going to Japan. Lost in Translation came out right when I turned 18 and captured my imagination like nothing else before it. I dream different because Lost in Translation. My music tastes changed because of Lost in Translation. What I valued in life changed because of Lost in Translation. It’s the only movie to rank this high where I don’t watch clips of it a lot (aside from the bar scenes) but it’s also important as one of the first movies where I relate and understand the female character more than the male. Even to this day I relate to Charlotte. Scarlett Johansson was 18 pretending to be 28 and even at 40 I feel her energy more than almost any other movie character. I think my love of karaoke came from this movie as well!

04. The Raid 2: Berandal

Full Watch: High
Clip Watch: High
Rent Free: High
Film Love: High
Film Importance: Mid
Recommendation: High

The best action film ever made.

Yes, I absolutely feel that way. From hand to hand to the car chases? I think nothing holds up like Raid 2. A lot of people criticize the plot, which details the cop in the first movie going undercover to infiltrate the gangs in Indonesia to try and stop corruption from the inside. It goes from this to basically just a guy involved in the gangs of Indonesia in a crime war having to react to the decisions by those trying to get to the top instead of being really about the corruption of the police, but for me? That’s the point. Rama got sent to stop corruption, but how do you stop something in the middle of chaos? All Rama can do is fight everyone because he’s the greatest fighter to ever be put on film. You believe in him more than anyone else. I’ve watched clips from this so many damn times, heck I was watching it again just a week or so ago with my dad. I’ll never tire of it. Come on Gareth Evans. Give me one more Raid with Iko Uwais before he gets too old. Maybe I’ll finally watch Wu Assassins.

03. The Nice Guys

Full Watch: High
Clip Watch: High
Rent Free: High
Film Love: High
Film Importance: High
Recommendation: High

You see that? You see that? Perfect rating. This is a true top three. The Nice Guys I think is the best comedy of the 21st century. It’s also the best crime action movie. It’s Shane Black at his purest making a movie for me. Russell Crowe? Check. Ryan Gosling? Check. Movie about Detroit corruption? Check. Neo-Noir? Check. Hannibal Buress as a bee? Check. It’s so funny. It’s so quotable. It’s so well made as you can watch it any time with any mood or feeling.

02. Blade Runner 2049

Full Watch: High
Clip Watch: High
Rent Free: High
Film Love: High
Film Importance: High
Recommendation: High

There’s a place inside me that feels like Blade Runner 2049 is my favourite movie ever made. It only came out a decade ago but it just hits everything I’ve wanted in a movie. One might say, well of course, you used to say that about Blade Runner. But I didn’t come into BR2K49 thinking it was going to be that for me. I had low expectations. I came out feeling it was better than Blade Runner.

I don’t just rewatch clips. My phone wallpaper is still Blade Runner 2049. I still have it as one of my rotating wallpapers on my desktop. I wake up to the Baseline test. Yes, on my phone, as one of my alarms, is Ryan Gosling taking his Baseline test.

I think the plot sidestepping the human or replicant question and instead dipping into what makes us human and what makes life have value was such a better question to make it about. I could talk and debate the movie with anyone. It’s near perfect. Often people criticize Jared Leto, and I agree David Bowie would have been better, but I don’t think he’s as bad as some try to make him out to be just because they don’t like him. I think he’s a good villain and is perfect for the modern times ideal of tech villains.

This is awful to admit, but the scene which Agent K strangles Luv? It’s one of my favourite scenes of the movie. I know it makes me sound morbid, but it’s because of how raw and brutal it is. You have these two programmed replicants who can fight at superior levels and what ends it? Some series of kicks and punches? No. A hand to the throat and a drowning. There’s no armbar reversal. There’s no humanity to it. That’s the point. The only way to put down this replicant was to strip the fight of its humanity and just do the most reprehensible level of murder one could do. Only looking down to make sure they died. It’s chilling. It will cause every nerve in your body to spark. And yet you can’t look away.

Two Ryan Gosling’s in my Top 3. You did it London boy. You did it.

01. Almost Famous

Full Watch: High
Clip Watch: High
Rent Free: High
Film Love: High
Film Importance: High
Recommendation: High

When I did my Fumbling Towards Forty on movies, I said Blade Runner 2049 was the best film but Almost Famous is my favourite film. My explanation falls right into the Rewatchable category. I can watch it any time, clip or full film (preferably Untitled) and it will make me happy. The movie had a significant influence in me going to college for journalism without me realizing it.

You see, back in the late 90s early 00s, we had illegal satellite and it used to show movies you could watch at any time. They’d stay for a month or two and slowly fall off. Fight Club was the first I watched like crazy. So much my mom still remembers. The next was Almost Famous.

It’s such a brilliant movie. It of course had me falling in love with Kate Hudson (who didn’t?) but it also just rewired my brain for what I wanted in my life. It made me value travel and taking a journey, trusting the unknown, and being okay with falling in love with something as stupid as a piece of music.

I’ve watched clips from it a million times, but I also don’t need to anymore, because when I say rent free? I can pretty much think of the whole movie in my head and watch it that way. That’s how deep it is for me. I think I’ve watched it every year since it came out. That’s why I couldn’t just do a 21st Century list.

It’s my comfort movie. It’s my life movie. It’s my most rewatchable movie.

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