By The Update (currently rewatching Tropic Thunder for the 43rd time)
5. Jerry Maguire (1996)
The Controversial Pick™
Yes, it’s technically a rom-dram-com hybrid with enough heart to choke a Pixar exec, but Cruise’s desperate, flailing charm is funny in exactly the way your ex-boyfriend thinks he is.
From screaming “SHOW ME THE MONEY” to that goldfish moment, he’s a charming, emotional mess.
Most Memorable Quote:
“You complete me.”
(Stolen from Jerry Maguire, perfected by The Joker, and now your cousin’s wedding vows.)
4. Risky Business (1983)
Cruise + Pantsless Dance = Cinema History
This is the one where Tom slides across the floor in tighty-whities and never looks back. It’s part coming-of-age, part capitalism horror story, part underwear ad.
Cruise plays Joel, a teenager who turns his house into a brothel and somehow learns responsibility? Sure. Whatever.
Most Memorable Quote:
“Sometimes you gotta say, what the f***.”
(…Which is also the unofficial motto of Cruise’s entire stunt career.)
3. The Firm (1993) – Kidding. Just seeing if you’re paying attention.
(No one laughs in The Firm. Not even the soundtrack.)
3. Tropic Thunder (2008)
Cruise Goes Full Gremlin
Bald, sweaty, and full of rage, Cruise’s Les Grossman is what happens when you feed Ari Gold after midnight. He’s offensive, unhinged, and somehow… unforgettable.
It’s like Cruise finally got to say everything he’s not allowed to in Scientology meetings.
Most Memorable Quote:
“I will rain down an ungodly f***ing firestorm upon you.”
(And honestly? We believed him.)
2. American Made (2017)
The Scam Artist Era
Cruise as Barry Seal, a coke-smuggling pilot with vibes straight out of Narcos: Florida Edition.
It’s based on a true story but plays like a madcap, “oops-I-just-started-a-cartel” dark comedy.
He’s in over his head. He smiles through it anyway. Classic Cruise.
Most Memorable Quote:
“I’m the gringo who always delivers.”
(Like Amazon Prime, but with felonies.)
1. Magnolia (1999)
Cruise Unleashed and Unhinged
Okay, this one’s more drama than comedy, but Cruise’s performance as a misogynist self-help cult leader is so darkly absurd it circles back to hilarious.
He’s sweating rage, screaming nonsense, and somehow makes “Tame the c***” a real workshop.
Most Memorable Quote:
“Respect the c***. And tame the c***!”
(…We have no follow-up. Just stunned silence.)
The Update Verdict:
People forget Cruise can be funny, probably because he’s spent the last two decades trying to kill himself on camera. But dig back into the archives and you’ll find awkward charm, corporate rage, and the kind of sweaty intensity that makes for comedy gold.
(One star for each time we’ve screamed “SHOW ME THE MONEY” into the void.)
