Film

Who's Your Caddy?

Name: Who's Your Caddy?
Genre: Comedy
Released: 2007
Cast: Big Boi, Jeffrey Jones, James Avery, Tony Cox, Terry Crews

Comedy
Light-hearted

A fish-out-of-water comedy about a hip-hop mogul crashing an exclusive golf club and refusing to leave. It's broad, fast, and operates entirely in the register of broad comedy — think stereotype-laden outsider comedy from the 2000s. For fans of comedies that swing for the fences without caring if they miss.

TMDb rating

1.7

Should you watch it?

Watch it if you enjoy broad, good-natured class-clash comedy where the jokes come from big personalities and rowdy set pieces rather than sharp satire, and you don't mind a film that's silly on purpose.

Skip it if you want sharp wit or a sober take on golf, since the gags are broad and the plot is a thin frame for them.

What it asks of you: A light, brisk ninety-one minutes with little to hold onto beyond the next bit; it asks you to switch off your critical eye and let the loud, cartoonish energy carry it.

Not sure? Find tonight's pick in a minute.

If you liked this

Caddyshack1980

The spiritual ancestor of all golf comedies: anarchic, quotable, and stacked with memorable characters and set pieces. It's genuinely funny and remains the gold standard.

But Moves at a looser, more meandering pace than modern comedies. Some younger viewers find it slow.

Coming to America1988

Eddie Murphy plays a fish-out-of-water prince navigating American culture and class with charm and impeccable comic timing. Rich world-building and genuine heart underneath the jokes.

But The fish-out-of-water premise itself is familiar now. Also quite long for a comedy at 117 minutes.

Tropic Thunder2008

A comedy that also commits to satire: absurdist, audacious, and unafraid to go big and weird. The performances are fearless and the movie finds real laughs in chaos.

But Wildly uneven in tone. Some sequences land harder than others, and the satirical edge can feel scattered.

Not sure tonight? Get a pick in a minute, starting from Who's Your Caddy?

The wildcard

Something you would not have found on your own.

Putney Swope1969

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Happy Gilmore1996

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Major League: Back to the Minors1998

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But Lean plot — it's mostly comedic set pieces strung together rather than a deeply involving story.

The Waterboy1998

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But The mother character is a pretty broad caricature. Also struggles with pacing in the middle stretch.

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But Many jokes don't land, and the film feels half-baked. The tone wavers between affection and mockery.

BASEketball1998

Trey Parker and Matt Stone's dumb-genius take on sports culture and corporate stupidity. If the premise appeals to you, the execution is surprisingly inventive.

But Aggressively silly in ways that will alienate many viewers. The humor is often juvenile and deliberately stupid.

Freddy Got Fingered2001

Tom Green's commitment to chaos and discomfort creates something unlike any other comedy. It's an endurance test, but genuinely odd and weirdly fearless.

But Hostile and deliberately off-putting in almost every way. Most viewers will find it exhausting rather than funny.

Summer with the gentleman2019

Both center on a successful outsider navigating worlds with rigid unspoken rules and discovering those rules are designed to exclude people like him. One plays it broad; one plays it sleek.

Guy Ritchie's ensemble crime-comedy about a cannabis kingpin and the chaos around him. Razor-sharp dialogue, clever structure, and a huge cast all clicking at once. Pure pleasure.

But Very British sense of humor and dialect-heavy dialogue; you have to keep up. Also quite graphic in places; the violence is real even when it's funny.

Showgirls1995

Both are movies about class, access, and refusal to be excluded from exclusive spaces — but Showgirls is sincere where it aims for trashy spectacle, making it a perverse mirror of the underdog comedy.

Paul Verhoeven's notorious camp masterpiece about ambition and exploitation in Las Vegas. It's genuinely trashy, visually audacious, and accidentally hilarious in almost every scene.

But Explicit sex and nudity throughout. The film is often unintentionally funny in ways the director didn't intend, and it's genuinely difficult to watch without irony.