Jeremy Piven and John Cusack

Actors Jeremy Piven and John Cusack both grew up in Evanston, Ill., and became buddies in high school. Cusack attended the Piven Theatre Workshop, founded by Jeremy’s parents, and the 80s icon and Entourage star later lived together.

Their relationship extended into Hollywood, as the pair has shared the screen in numerous films, most notably Grosse Pointe Blank, Say Anything…, and Serendipity.

Unfortunately, though neither of them have spoken much about it, it’s been reported that they are no longer close.