Wander Boy: 10 Comical Paul Rudd Movie Moments

With his sparkling blue eyes and disarming smile, Paul Rudd plays insecure like nobody's business, and he comes by it honestly: before breaking out in 1995's Clueless, he grew up in the 'burbs DJ-ing Jewish bar mitzvahs under the name "Donnie the Dweeb." Today he balances those pretty-boy looks with that sincere, self-conscious charm to make us laugh, whether he's playing the uptight straight man with a goofy friend (Role Models, Dinner for Schmucks), or the loser who wants his cheating girlfriend back (The 40-Year-Old Virgin), or the handsome oddball (Anchorman: The Legend of Ron Burgundy). In his latest, Wanderlust, he stars with Jennifer Aniston as New Yorkers who pack up and move to a freewheeling community where the only rule is to be yourself. Here, some high points of Rudd's career (warning: some clips contain offensive language, if that sort of thing concerns you).

1. Our Idiot Brother

Rudd starred as the always cheerful, too-honest, pot-growing brother to three women (Emily Mortimer, Zooey Deschanel and Elizabeth Banks), whose homes he takes turns living in after a misunderstanding lands him in jail. It was an uneven movie saved by Rudd's winning performance.

2. Dinner for Schmucks

After 40-Year-Old Virgin, Rudd re-teamed with funnyman Steve Carell for Dinner for Schmucks – based on a French farce about a dinner party to make fun of the idiot guests invited. Tim (Rudd) is a rising exec who invites Barry (Carell), a tax inspector who creates mice dioramas as a hobby, to the dinner to impress his bosses. Problem is, Barry is doing way more harm than good to Tim's personal life, whether it's bringing on the back pain or causing a break-up between him and his girlfriend.

3. I Love You, Man

In this bromance, Rudd plays a nebbishy real estate agent who realizes on the eve of his wedding that he has no guy friends to be his man of honor. What to do? Audition for the role of course—and he ends up having unlikely chemistry (both in the plot and on the screen) with Jason Segal's carefree Sydney.

4. Role Models

Here Rudd stars as an embittered energy drink promoter who's dishing out snark to everyone, including the barista. After a mishap with his partner (Sean William Scott) that lands them both community service time in a big brother program, Paul is paired with a role-playing geek while Sean gets stuck with a foul-mouthed kid. The results are as laugh inducing as they are heartwarming.

5. Forgetting Sarah Marshall

Although he had a bit part in Forgetting Sarah Marshall as a down-to-earth surf instructor, Rudd steals just about every scene he's in. Teaching Jason Segel to surf is sort of an overstatement in the clip below, and the sage surfer advice he dispenses to the heartbroken guy make for hilarious quips of wisdom.

6. Knocked Up

In this movie that launched the return of the R-rated comedy, Rudd plays Katherine Heigl's brother-in-law who partakes in a fantasy baseball draft after hours in order to avoid his wife. Complaining that marriage isn't all roses, Rudd delivers one of his best lines in the film when he compares real life marriage to a hit TV series. "Marriage is like an unfunny, tense version of Everybody Loves Raymond but it doesn't last 22 minutes, it lasts forever." Ouch.

7. The 40-Year-Old Virgin

Steve Carell won over audiences in The 40-Year-Old Virgin but it was Paul Rudd's whip-smart "You know how I know you're gay?" back-and-forth exchange with Seth Rogen that stole the spotlight. Rudd would go on to make several more movies with Judd Apatow.

8. Wet Hot American Summer

The place – Camp Firewood. The year – 1981. It's the last day of summer camp before everyone returns to the real world and there's unfinished business to attend to. Rudd stars as Kate's cute, rebellious, obnoxious and unfaithful boyfriend in this film that has achieved a cult following.

9. 200 Cigarettes

Before Garry Marshall gathered together a bunch of actors for New Year's Eve, there was 200 Cigarettes, in which Rudd's character Kevin and Courtney Love's Lucy are struggling with the sexual tension between one another. Rudd feeds off of Love's character and vice-versa in their scenes with hilarious results.

10. Clueless

Alicia Silverstone as Cher was the star of this clever comedy that launched Rudd's career, but he was a true find as the good-natured stepbrother who serves as an affable foil to Cher's spoiled-teen ways—and ends up winning her heart.