Last Updated on August 3, 2021
1. RON BURGUNDY – ANCHORMAN (2004)
Is there a more quotable movie in the last twenty years? Is there a more lovable asshole in the history of film? Is there a better way to end this list? Nope, see ya.
2. FRANK RICARD – OLD SCHOOL (2003)
The legend that is “Frank the Tank” could only be pulled off by Will in his prime. The guy did it all – beer bongs, streaking, kidnapping, petroleum jelly refereeing, fighting gay blow-job coaches, and ribbon dancing. All while going through a separation and holding down one hell of a mid-life crisis. This entry also includes my favourite Will Ferrell moment ever….
3. BUDDY – ELF (2003)
The perfect role for Will with his wide-eyed innocence and abnormally long awkwardness. This is quickly becoming a holiday staple around these parts if only because I like to sing all the songs and love it when kids get hit in the face with snowballs.
4. STEVE BUTABI – A NIGHT AT THE ROXBURY (1998)
A guilty pleasure of mine, ROXBURY is one of those movies I watch any time it’s on, in it’s entirety. Some of Will’s funniest moments ever take place as Steve, one half of the sweetest pair of brothers in nightclub history.
5. RICKY BOBBY – TALLADEGA NIGHTS (2006)
Cinema’s greatest stock car driver since Cole Trickle knows how to lay a patch down when it comes to the world of fake car racing. Thems is some bad-ass sideburns too. I wonder if NASCAR fans love or hate this movie. I’ll never know, NASCAR fans don’t talk to me.
6. MUGATU – ZOOLANDER (2001)
Mugatu wants the Prime Minister of Malaysia dead and has decided to train one of the world’s top fashion models to do the trick for him. All evilness is thwarted however and the world is made a better place with the grand opening of “The Derek Zoolander Center For Kids Who Can’t Read Good And Wanna Learn To Do Other Stuff Good Too’, of which I’m an alumni by the way.
7. MARSHAL WILLENHOLLY – JAY & SILENT BOB STRIKE BACK (2001)
Named after the three main characters from the 70’s Saturday morning children’s program, ‘Land of the Lost’, Willenholly screws up everything he comes in contact with as Jay and Silent Bob escape his clutches by pretending to be gay lovers with an orangutan for a son.
8. CHAZZ REINHOLD – WEDDING CRASHERS (2005)
The greatest wedding crasher of all time has fallen on dark times as he prowls the world of funerals and grieving hotties to get his action. It doesn’t seem to phase him though, as long as he’s still getting some ass and a warm plate of meatloaf every so often.
9. MUSTAFA – AUSTIN POWERS 1&2 (1997, 99)
I think the guy died three or four times over the course of both movies but even that wasn’t enough to keep Will from leaving his classic cameo mark. He was the ultimate killing machine who would never reveal his secrets. Unless, of course, you asked him about said secrets three times, which really annoys him into submission.
10. BIG EARL – STARSKY & HUTCH (2004)
Thank God this guy is locked up. Society isn’t ready for his unearthly obsession of dragons and male belly buttons. I pity Earl’s cell mate, constantly having to walk up and down the isle while slow turning and acting scary. I’m afraid there is no rehabilitation for these things.
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