Tommy Boy (1996)

Funniest Comedies Tommy Boy
Paramount Pictures

Chris Farley and David Space established themselves as one of our favorite comedy movie duos before Farley’s death cut short their partnership after just two movies — Tommy Boy and the also-funny Black Sheep.

Farley’s earnest sweetness and Spade’s wry cynicism make for a perfect road trip movie filled with jokes we think about every day — fat guy in a little coat, “Why I suck as a salesman,” and “what’d you do?”” especially.

And we couldn’t relate more to the scene that ends with Farley and Spade crying along to the Carpenters’ “Superstar.” We love this movie.