Film
The Ex
A romantic comedy about a struggling guy forced to work at his in-laws' ad agency while navigating office politics and a tense rivalry with his wife's ex-boyfriend. It's a mid-2000s studio comedy that leans on cast charm more than originality, aiming for laughs from workplace chaos and relationship anxiety. Perfect if you like ensemble casts and don't mind formula.
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Wedding Crashers2005
Two leads with genuine chemistry navigating romantic entanglement and family chaos. Smart enough to know what it is, funny enough to earn your time, and packed with a supporting cast who understand comedy timing.
But It's a bro-comedy from 2005 that hasn't aged gracefully in places. If you're looking for anything besides witty banter and romantic hijinks, you'll leave disappointed.

I Love You, Man2009
Another underachiever-meets-in-laws story, but with more heart. Paul Rudd and Jason Segel's friendship feels earned, and the film balances its ensemble cast without losing focus on what actually matters.
But It's still very much a product of its era. The buddy-romance formula can feel thin if you've seen too many of these already.

The Break-Up2006
Vince Vaughn and Jennifer Aniston in a relationship comedy that actually cares about tension and character quirks. Sharper dialogue and a willingness to let things be awkward elevates it above standard fare.
But The romantic resolution feels forced after spending so long on genuine conflict. Some scenes drag longer than they need to.

Not sure tonight? Get a pick in a minute, starting from The Ex
The wildcard
Something you would not have found on your own.
Thank You for Smoking2005
Both are workplace comedies about men struggling with ambition, fatherhood, and fitting into rigid professional worlds, but this one has an actual point of view.
Same era, same ensemble sensibility, but infinitely sharper. It takes the workplace-comedy setup and uses it to actually say something. Aaron Eckhart is a lobbyist navigating fatherhood, corporate pressure, and moral compromise—all handled with wit and intelligence that The Ex never attempts.
But It's a satire that requires you to pay attention. No broad setpieces or easy laughs; the humor lives in the writing and subtext. Much darker in its worldview.

More like this (8)
Old School2003
Will Ferrell, Vince Vaughn, and Luke Wilson in absurdist comedy that doesn't try too hard to make sense. Genuinely inventive set pieces and committed performances make this consistently funny.
But The humor is broad and occasionally mean-spirited. It's also aggressively male-centered in a way that hasn't held up particularly well.

Forgetting Sarah Marshall2008
Jason Segel and Kristen Bell navigate heartbreak with humor that feels human. The ensemble is likeable, the laughs are genuine, and it understands that romance is messy before it's cute.
But The first act takes a while to recover from its opening heartbreak. If you're not invested in the emotional stakes, the comedy loses some land.

27 Dresses2008
Katherine Heigl and James Marsden have natural chemistry in a rom-com that doesn't condescend to its audience. The premise is genuinely clever, and the supporting characters are more than cardboard cutouts.
But It hits every beat of the romantic-comedy playbook without deviation. If you know the formula cold, there's nothing here to surprise you.

Just Friends2005
Ryan Reynolds and Amy Smart in a comedy that's aware of its own ridiculousness. The hometown-hero-returns-transformed plot gets some actual emotional weight alongside the broad jokes.
But The humor oscillates wildly between sarcastic and slapstick. If that tonal inconsistency bothers you, the film will feel shapeless.

The Hangover2009
A comedy that builds perfectly and executes on every joke. The ensemble—Zach Galifianakis, Ed Helms, Bradley Cooper—works as a unit, and the mystery structure gives it momentum beyond just gags.
But The humor is aggressively male, and some of its comedy hasn't aged well. It's also become so quotable that fresh viewings feel like rewatching a billion TikToks.

DodgeBall: A True Underdog Story2004
Vince Vaughn and Ben Stiller in a film that understands parody. It's ridiculous, committed, and surprisingly quotable. Laughs land because the movie is in on the joke with you.
But If you don't like absurdist humor or admire subtlety, this will feel like being yelled at for ninety minutes. The plot is basically nonexistent.

Eternal Sunshine of the Spotless Mind2004
Both revolve around a man trying to understand his place in a relationship and what he's supposed to want, but this film trusts you to feel rather than just laugh.
Another Zach Braff lead, but in a film that takes the romance-and-regret premise seriously. It's tender, philosophical, visually inventive, and genuinely moving. Watching him here reveals what he's actually capable of as an actor.
But It's experimental and melancholic. There's little traditional plot, and the tonal register is the opposite of a studio comedy. Some find it too precious; others think it earns every moment.

Glengarry Glen Ross1992
Both films center on a protagonist in an advertising/corporate world facing pressure and rivalry, but where The Ex aims for laughs, this one aims for your throat.
The dark side of the workplace comedy. A masterclass in ensemble acting—Harris, Arkin, Lemmon, Mamet's dialogue—showing how competition and desperation corrode the soul. It's what happens when the stakes are real and the jokes run out.
But It's a play about failure, greed, and male dysfunction. There's almost no warmth here. Brutally cynical and absolutely relentless.

People
Cast
Zach BraffTom Reilly
Amanda PeetSofia Kowalski
Jason BatemanChip Sanders
Charles GrodinBob Kowalski
Mia FarrowAmelia Kowalski
Lucian MaiselWesley
Donal LogueDon Wollebin
Amy PoehlerCarol Lane
Fred ArmisenManny
Bob StephensonDoug
Yaffit HallelyWoman
Josh CharlesForrest Mead
Directing
- Jesse PeretzDirector
- Daniel J. ShawFirst Assistant Director
- Mariana HellmundScript Supervisor
- Maggie MurphySecond Assistant Director
Writing
- David GuionWriter
- Michael HandelmanWriter
Production
- Jeanne McCarthyCasting Director
- Couper SamuelsonCo-Producer
- Marc ButanExecutive Producer
- Mark CubanExecutive Producer
- Ray AngelicExecutive Producer
- Todd WagnerExecutive Producer
- Anthony KatagasLine Producer
- Anne CareyProducer
- Anthony BregmanProducer
- Ted HopeProducer
- Erica KayProduction Supervisor
- Ray AngelicUnit Production Manager