I’m searching for some really good comedy movies to watch but I keep seeing the same titles everywhere. I want to laugh and enjoy something new or maybe classic that I haven’t seen yet. What are your favorite comedy films and why do you love them?
What Your Favorite Comedy Says About You (Millennial Edition)
Okay, don’t come at me, but I swear your taste in comedies totally exposes what era you grew up in. I was born in the golden “Pizza Hut birthday party, Game Boy in pocket” years (aka the millennial zone), so my go-to laugh fixes probably look a little different from someone raised on TikTok or VHS.
Let’s break it down—the actual repeat-worthy movies I can never get tired of. Yeah, some are outdated, some are straight-up weird, and all of them get me every single time.
White Chicks (2004)
You ever watch something so extra you can barely stand it but you can’t look away either? That’s White Chicks for me. The disguises are wild (does anyone remember how wild those makeup jobs looked?!), and the awkwardness is epic. This movie feels like cringe dancing at a middle school party—painful but hilarious, and weirdly comforting the older you get.
The Hangover (2009)
Not going to lie, I’d pay real cash money just to have this movie wiped from my brain so I could watch the first wild viewing again. Bachelor party in Vegas, total blackout, misplacing the groom, finding a freaking tiger in the dang hotel bathroom? Comedy gold, pure and uncut. Even now, years after the memes stopped, if I’m flipping around and this is on, I’m stuck for the next two hours. Zero regrets.
Clueless (1995)
Let’s get something straight—Clueless isn’t just “so 90s,” it’s basically the 90s’ entire personality. The iconic outfits! The weird slang! Yes, it’s got that high school all-American drama, but mostly it’s about Cher trying to do good in her own spectacularly clueless way. It’s got layers: fashion inspo, sassy one-liners, and a weird wholesome twist under the surface.
Superbad (2007)
Scene: Two awkward teens on an epic quest for cheap beer and high school (maybe accidental) infamy, except everything is going off the rails—fast. The jokes are raunchy, the situations totally chaotic, and yet somehow, you kind of want to hug all the characters by the end.
How many times have I rewatched Superbad? Can’t count. Not sorry.
Quick Side Note on Watching Movies (for Mac Users)
This is less of a hot take and more of a survival tip: If you’re on Mac and you like actually watching your favorite old comedies the way you want (not dealing with format errors and janky playback), check out Elmedia Player. It does subtitles without weird delays, pretty much handles any file you throw at it, and if your laptop’s too tiny, it streams in 4K to your big screen without making everything look like a slideshow. Works nice with Apple TV and Chromecast too.
TL;DR
Pick any of these for a throwback laugh night and you can’t go wrong. Bonus points if you share your own “this never gets old” pick—especially if you’re not a millennial. Always down to expand my watchlist.
So—what’s your comfort comedy?
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Honestly, as much as I love @mikeappsreviewer’s millennial throwback picks (I mean, “White Chicks” is pure chaotic energy and “Superbad” basically raised half my friends), I totally get the urge to go off the beaten streaming path. If I see “The Hangover” or “Bridesmaids” on just ONE more recommendation list I might implode.
Let me toss a few curveballs:
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Popstar: Never Stop Never Stopping (2016). Way too slept-on. If you dig Lonely Island humor and mockumentaries, it’s like “Spinal Tap” but with pop stars and 10x more absurdity. The songs will get stuck in your head. “I’m So Humble” is honestly an anthem for anyone who basically isn’t.
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Death of Stalin (2017). Ok it’s a “political satire” but don’t bounce yet—everyone in it is doing dry, deadpan British comedy played straight, and Steve Buscemi as Nikita Khrushchev is comedy gold. It’s dark and zany and I snorted coffee outta my nose.
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Palm Springs (2020). Yeah, it got buzz, but somehow still not enough. It’s not a straight-up “look at these goofy guys” comedy, but the whole stuck-in-a-time-loop thing is done way funnier than most, and Andy Samberg is perfection.
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What We Do in the Shadows (2014). Absolutely essential if you love awkward humor (and vampires bumbling to pay rent in New Zealand). Jemaine Clement and Taika Waititi are masterclass. WAY better than the series, no contest.
Random classic for “never gets old”: Galaxy Quest (1999). Why? It’s a perfect parody of sci-fi fandom, Alan Rickman in a rubber forehead, Sigourney Weaver swearing at computers, and it’s genuinely sweet-hearted. 10/10 background-movie while you crush pizza rolls.
Anyone else wanna fight me about “Hot Rod” being massively underrated? Or am I just alone on this island…
What’s one weird comedy you’d defend with your life? I wanna build a watchlist that isn’t just “Step Brothers” and “Dumb and Dumber” again. Hit me!
Nobody talks about BASEketball (1998) anymore and I’m offended. It’s South Park humor BEFORE South Park got mean and the deadpan delivery just slaps. @mikeappsreviewer and @viaggiatoresolare threw down solid picks (and yeah, Popstar is criminally slept-on), but y’all forgot how dumb-funny sports can get.
For something way off people’s radar, hunt down Four Lions (2010). It’s a pitch black British comedy about wannabe terrorists that is so wrong, but honestly, I cried laughing. Riz Ahmed before he was cool. You want “new classic,” trust me.
Also, if you’re willing to risk subtitles, The Intouchables (2011) is French feel-good that will reset your mood without insult gags or Vegas bachelor parties. Not EVERYTHING funny needs to be American, sorry not sorry.
Oh, and anyone clowning on Elmedia Player hasn’t used it. I dare you to play old AVI or FLV files in QuickTime without hurling your laptop out the window.
Anyway, skip Step Brothers for the 900th time and give those a shot. Anyone else got a misfit hidden gem?
Let’s do this: everyone’s got their nostalgia picks, but if you want to dodge the basic “re-watch Anchorman for the millionth time” cycle, you have to dig a little weirder or, frankly, yank stuff out of the vault nobody dusts off.
First off, I’m with the folks hyping White Chicks and Superbad (yep, not subtle but sometimes you need dumb-funny). But let me throw you a wildcard: Hot Rod (2007). It’s Andy Samberg and crew LEVEL absurd. You’ll know in 20 minutes if it’s your style, but it’s a cult classic if you dig random, physical, surreal gags.
Another underrated riot: Popstar: Never Stop Never Stopping. It’s Lonely Island at their best, and barely anyone’s seen it. Think Spinal Tap but for the Instagram age.
Stepping outside of Hollywood? Hunt for the Wilderpeople (2016, Taika Waititi) is rolling-on-the-floor funny and manages to be all heart, zero cynicism. For British insanity, In the Loop (2009) feels like the political version of Superbad for grownups—Peter Capaldi’s swearing alone is art.
As for BASEketball and Four Lions, love those deep cuts from the others, but honestly Four Lions walks the tightrope between hilarious and uncomfortable BETTER than most dark comedies. Respect for throwing in The Intouchables too—weirdly wholesome and charming.
Bottom line, if you want a night of left-field laughs and less deja-vu, queue up Hot Rod, Popstar, Hunt for the Wilderpeople, and Four Lions. Forget comfort zone, go for the oddball. And if someone suggests watching Step Brothers again—I dunno, maybe you DO need new friends.