9 Milestones in the Evolution of Paul Rudd

In Our Idiot Brother, Paul Rudd plays the shaggy-haired titular character, a guy so naively idiotic that he hands a uniformed police officer marijuana after the cop claims to be having a bad day. How did Rudd transform himself from a socially conscious law student who romances his hot ex-stepsister in Clueless to a socially imbecilic drifter who yearns for his dog Willie Nelson? You can always trace a direct line through a few important roles to illustrate what led to an actor's current success. As such, let's look at nine pivotal performances that track the evolution of Paul Rudd.

Clueless (1994)

After a series of small parts in TV movies and a recurring role on the short-lived Fox sitcom Wild Oats, the University of Kansas graduate earned what would be his breakthrough part in Amy Heckerling's '90s gem Clueless. Rudd reportedly auditioned to play Murray (which went to Donald Faison), Elton (Jeremy Sisto) and Christian (Justin Walker), but Heckerling cast the 25-year-old as Alicia Silverstone's onscreen ex-stepbrother and eventual love interest -- a role that earned him the title of MTV audience crush object. Over a decade later, Rudd would re-team with Heckerling less successfully for the straight-to-DVD flop I Could Never Be Your Woman.

Halloween: The Curse of Michael Myers (1995)

Just two months later, Rudd (who was still being credited as Paul Stephen Rudd at the time) returned to the box office for his first leading role. In the sixth installment of the Halloween franchise, which was filmed before Clueless, the Kansas U. grad replaced Brian Andrews as Tommy Doyle, the adult version of the child that Laurie Strode babysat in the first Halloween film. Although critics hated the movie, it did decently at the box office, coming in second to David Fincher's Se7en its opening weekend.

Cider House Rules (1999)

Four years later -- after playing the object of Jennifer Aniston's affection in, well, The Object of My Affection and appearing in MTV's ensemble bomb 200 Cigarettes -- Rudd earned his first role in a marquee drama. In Lasse Hallström's adaptation of the best-selling novel of the same name, Rudd played Charlize Theron's apple farm owner boyfriend who leaves her to fight in World War II. Cider House Rules would be the most critically successful drama of Rudd's career and also his only Academy Award-winning title. (The film won Best Adapted Screenplay and Best Actor in a Supporting Role for Michael Caine.)

Wet Hot American Summer (2001)

At this point in his career, Rudd was being recognized as a serviceable dramatic actor and romcom love interest but he had not yet had the chance to display his serious comedic talents. That would change with David Wain and Michael Showalter's summer camp cult classic Wet Hot American Summer. Opposite Janeane Garofalo, David Hyde Pierce, Elizabeth Banks, Michael Ian Black, Bradley Cooper, Amy Poehler and more, Rudd played an inattentive boyfriend/lifeguard who rocks a sweet jean jacket. While the film received negative reviews at the time of its release, it has since accumulated a devoted following that is praying for a prequel.

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