Entertainment TV & Film The Five Funniest Chevy Chase Movies The best movies from an icon of '80s comedy Share PINTEREST Email Print Mark Mainz/Getty Images TV & Film Movies Comedies Best Movie Lists Science Fiction Movies War Movies Classic Movies International Movies Movies For Kids Horror Movies Movie Awards Animated Films TV Shows By Patrick Bromley Patrick Bromley is an entertainment writer and the editor-in-chief of "F This Movie." Previously, he worked as a reporter and critic for the Chicago Sun-Times News Group. our editorial process Patrick Bromley Updated February 22, 2019 Chevy Chase left Saturday Night Live to pursue a movie career after just one season. Though he's been acting on the big screen for four decades, his best work was in the '80s, when he was one of the biggest comedy stars in America. These are the funniest movies Chevy Chase ever made. 01 of 05 Caddyshack (1980) Warner Bros. Though Caddyshack isn't quite the comedy classic it's so often made out to be, its best moments belong to Chevy Chase. He plays carefree golf pro/playboy Ty Webb, a guy who's great at the game but who takes none of it seriously, and it's the first role to make use of everything Chase was best at since leaving Saturday Night Live. The problem with the golf comedy Caddyshack is that all of the actors are funny, but they're in different movies: the always great Bill Murray is in one movie, while Rodney Dangerfield is in a different one. Chevy Chase is in a third movie. His is the funniest. 02 of 05 National Lampoon's Vacation (1983) Warner Bros. The movies Chevy Chase made after leaving Saturday Night Live had him doing more of the same — sarcastic cool guy (Caddyshack) or romantic leading man (Foul Play). But it was in the John Hughes-scripted, Harold Ramis-directed Vacation that Chase found perhaps his best screen persona — the lovable everyman, the doofus with a heart of gold, the guy whose heart is in the right place but who can't quite do anything right trying to get his family to the Wally World theme park. The character and the movie were so successful that Chase reprised it three more times in a series of sequels of varying quality, plus one Old Navy commercial in 2012 and a reboot/remake in 2015. Chase has never been funnier on screen in a role that combines his flair for physical comedy, sweetness and an unwavering ability to mess up. The movie is great, the writing is strong, but Chase is the reason the movie is a classic. 03 of 05 Fletch (1985) Universal While National Lampoon's Vacation gave Chase his best role, his work in Michael Ritchie's detective comedy Fletch capitalized most on the comic persona he had been honing since SNL. Based on a famous series of novels by Gregory McDonald, Fletch casts Chase as Irwin M. Fletcher, an investigative journalist uncovering a scandal after being offered money to kill a man. In the role, Chase is faster, funnier and cooler than everyone, constantly dressing up in disguises and taking on different characters. It's the ultimate expression of the ironic distance of Chase as a performer — Fletch is buried under several layers of personalities, so we never really get to know him. Same goes for Chase. 04 of 05 Three Amigos! (1985) HBO Chase isn't at his best in this 1985 John Landis comedy (which was co-written by musician Randy Newman and Saturday Night Live executive producer Lorne Michaels), but it makes the list of his funniest movies because of the chemistry between him and co-stars Martin Short and Steve Martin. As three silent movie stars mistaken for actual heroes, all three comedy icons find different ways to be funny and are clearly having a great time working together. 05 of 05 National Lampoon's Christmas Vacation (1989) Photo courtesy Warner Bros. Not only is National Lampoon's Christmas Vacation one of the best holiday comedies ever made, not only is it one of the best comedy sequels ever made, but it also edges out Funny Farm and Spies Like Us as one of Chase's best. After the terrible European Vacation, it was good to see Chevy and the Griswolds bounce back in this very episodic but very funny movie, which provided a return to form for Chase, who brings back everything that we once liked about Clark Griswold. Christmas Vacation is also notable because it might just be the last great comedy Chase ever made.