Jeremy Piven as Ari Gold in ‘Entourage’

Actor Jeremy Piven offers his character's signature smirk in this 2005 PR photo from the second season of the HBO series Entourage. Piven played Ari Gold, a sometimes-ruthless, sometimes-hapless Hollywood talent agent in the series, which ran for eight seasons from 2004-11. Jeremy Piven was born in 1965, so he turned 40 the year this photo was released.