Photo: Dimitrios Kambouris/Getty Images North America

In a biz where success is more often fleeting than not, Paul has had some serious staying-power. His breakout performance in the ’95 film Clueless, turned him into a bit of a teen idol. He garnered more recognition with a recurring role on Friends as Mike Hannigan, Phoebe’s eventual husband. But Paul became a full-fledged comedy star with his co-starring roles in a bevy of Judd Apatow and Seth Rogan films including The 40-Year-Old Virgin, Anchorman: The Legend of Ron Burgundy, and Knocked Up. Paul has also become an indie-film fave with starring roles in The Oh in Ohio, The Ten, and more.

Most recently he headlined Jason Segel’s I Love You Man as Peter Klaven, a just-engaged real estate agent who needs to find male friends in order to have a best man for his wedding.  He also lent his voice to the star-studded Dreamworks animated hit Monsters vs. Aliens. In the screwball film Dinner for Schmucks, he was reunited with Steve Carrell for the first time since The 40 Year Old Virgin as Tim Conrad, a mid-level financial exec who is invited by his boss to the coveted “dinner for idiots” where the  high-rolling guests compete for a trophy by bringing the strangest, most eccentric person possible. The RomCom How Do You Know opposite Reece Witherspoon, Owen Wilson, and Jack Nicholson followed. He is poised to star in Wanderlust, due out later this year, with Jennifer Aniston as a married couple who tries to escape modern society by leaving their cushy lives in New York. Here, he is impossibly dapper on the red carpet in these Tom Ford shades. –rpuccia

Buy these now: Tom Ford FT0126, $253