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He is best known for his roles as Ari Gold in the comedy series Entourage, for which he won a Golden Globe Award and three consecutive Emmy Awards, and as Spence Kovak on Ellen De Generes's sitcom Ellen.
He also starred in the British period drama Mr Selfridge, which tells the story of the man who created the luxury English department store chain Selfridges. He also attended Drake University in Des Moines, Iowa, where he departed after his sophomore year to attend New York University's Tisch School of the Arts.
He has appeared in a number of films with John Cusack, who is also from Evanston and is a fellow alumnus of the Piven Theatre Workshop (as are Cusack's sisters Joan and Ann).
In 2007, Piven appeared in the video for "Drivin' Me Wild", the third single taken from rapper Common's seventh album Finding Forever.