1. Bill Lumbergh – Office Space
Photo credit: FoxGary Cole may not have starred in Office Space, but he certainly stole every scene he was in with his portrayal of smug business executive Bill Lumbergh.
2. Steve Stifler – American Pie
Photo credit: UniversalAs frat-boy jock Steve Stifler, Sean William Scott relentlessly and hilariously mocked Jason Biggs and pals during their quest to lose their virginity by prom night.
3. Kip Dynamite – Napoleon Dynamite
Photo credit: Fox SearchlightWhen he wasn’t busy “online chatting with babes,” Napoleon’s older brother kept audiences laughing by romancing his new girlfriend Lafawnduh and forming a fledgling tupperware sales business with Uncle Rico.
4. Chunk – The Goonies
Photo credit: Warner Bros.A childhood favorite for many, The Goonies was full of classic characters and scenes. Perhaps the most memorable, and funniest, though, was the special bond that formed between chubby scaredy-cat Chunk and his new outcast pal, Sloth.
5. Carl Spackler – Caddyshack
Photo credit: Warner Bros.Bill Murray’s turn as Bushwood Country Club greenskeeper Carl Spackler was comedically brilliant, especially since much of it was improvised.
6. Billy Madison – Billy Madison
Photo credit: UniversalThe movie that made Adam Sandler a star was ridiculous, absurd, and hilarious. It paved the way for Sandler’s brand of silly, stupid humor for years to come.
7. Tommy Callahan – Tommy Boy
Photo credit: ParamountChris Farley scored his biggest hit with this portrayal of likable, but dim, auto parts heir Tommy Callahan.
8. Inspector Clouseau – Pink Panther Series
Photo credit: United ArtistsPeter Sellers is hysterical and brilliant at playing incompetent Inspector Clouseau. He runs into trouble at every corner, and brings out a lot of laughs.
9. Peter Venkman – Ghostbusters
Photo credit: ColumbiaBill Murray has had dozens of hit movies, but perhaps his most memorable are the Ghostbusters movie. Along with pals Dan Akroyd and Harold Ramis, Murray cracks wise as the team saves New York City and Sigourney Weaver from paranormal activity.
10. Bruno – Bruno
Photo credit: UniversalAustrian fashion guru Bruno has his own fashion TV show. After he disgraces himself in front of his fans, he heads to America to become a celebrity. The whole adventure is just hilarious.
11. Derek Zoolander – Zoolander
Photo credit: ParamountCursed with being “really, really, really, ridiculously good-looking,” male model Derek Zoolander also must stop an evil designer’s brainwashing scheme in this side-splitting send up of the fashion world.
12. Ron Burgundy – Anchorman
Photo credit: DreamWorksIn one of Will Ferrell‘s biggest roles, he plays dense 1970’s news anchor Ron Burgundy, who is shocked by the idea that a woman can also the read the news. Stay classy, San Diego.
13. Lloyd Christmas – Dumb & Dumber
Photo credit: New LineIn one of the most quotable movies ever made, Jim Carrey sets out for Aspen with pal Jeff Daniels to return a briefcase of money to the girl of his dreams.
14. Alan – The Hangover
Photo credit: Warner Bros.As the groom’s odd and socially-awkward future brother-in-law, Zach Gallifinakis turned a funny movie into a side-splitting fan favorite. Along the way, Alan added three new members to his wolf pack.