#19: The Roxbury Guys, Debuted in 1996
Another SNL skit-turned-film, The Roxbury Guys, is an excellent example of how a simple idea can be transformed into a memorable performance. Starring Will Ferrell and Chris Kattan, their characters are similar to their roles in the film, whereby two obnoxious guys go out on the town and try their luck at meeting women.
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Their aggressive and offputting attempt at flirting has women running for the hills. The skit was joined by famous actors such as Tom Hanks, Alec Baldwin, and even Sylvester Stallone as his character, Rocky Balboa. But the most iconic A-lister to join the skit has got to be Jim Carrey, who took on the role almost too well.