Jeremy Piven

A former member of the Second City National Touring Company, Piven made his small-screen debut on Carol Burnett's short-lived variety show Carol and Company in 1990. He went on to play a writer on HBO's The Larry Sanders Show and to appear on Seinfeld before starring as an unemployed father on the short-lived series Pride & Joy. Disney, who produced Pride & Joy, then created a role for him on Ellen. After the sitcom's cancellation in April 1998, Piven landed his own show, the offbeat ABC comedy-drama Cupid. Also starring Piven's real-life neighbor Paula Marshall, Cupid followed the infamous matchmaker after he had been thrown out of heaven for bad behavior and attempted to earn his reentry by uniting 100 couples in true love without using his otherworldly powers. The series won critical acclaim and earned Piven quite a following. Yet, as with many of the network's more innovative shows, ABC mishandled Cupid, shuffling it in and out of prime time until its inevitable cancellation. Undaunted, Piven returned to television a year later to guest star on Will & Grace.

While Piven's film career has suffered the same ups and downs as his time on television, it is marked by numerous scene-stealing supporting performances. After making his feature-film debut in Lucas (1986), the actor appeared in Robert Altman's The Player (1992), Cameron Crowe's Singles (1992), and Tim Robbins' Bob Roberts (1992). He fell into a slump with failures like Judgment Night (1993) and Car 54, Where are You? (1994), but became a cult favorite for his portrayal of a campus misfit in P.C.U. (1994). Standout roles opposite Sarah Jessica Parker in Miami Rhapsody (1995), Robert De Niro in Heat (1995), Bill Murray in Larger Than Life (1996), and Morgan Freeman in Kiss the Girls (1997) quickly followed. He then proved to be the only good thing in Peter Berg's Very Bad Things (1998), before playing Nicolas Cage's best friend in The Family Man (2000). Piven took a respectable dramatic turn as a doomed helicopter pilot in Ridley Scott's award-winning Black Hawk Down, but returned to comedy for Old School (2003), a film by the makers of Road Trip (2000).

Then, in 2005, Piven scored the iconic role of Ari Gold on the HBO series Entourage. The show turned out to be a massive success, and Piven's profile was raised considerably, making him more of a household name, and helping him to score more interesting roles outside the show, like washed-out magician Buddy Isreal in the 2006 over-the-top action blow-out Smokin' Aces, and Damon Schmidt in the 2007 political thriller The Kingdom. In 2008, he joined the cast of the Guy Ritchie London crime movie RocknRolla. ~ Aubry Anne D'Arminio