Adrian Grenier Vincent Chase Actor Kevin Connolly Eric Murphy Actor Kevin Dillon Johnny "Drama" Chase Actor Jerry Ferrara Turtle Actor Jeremy Piven Ari Gold Actor Rex Lee Lloyd Actor Perrey Reeves Mrs. Ari Actor Emmanuelle Chriqui Sloan McQuewick Actor Gary Cole Andrew Klein Actor Scott Caan Scott Lavin Guest Star Rhys Coiro Billy Walsh Guest Star Jonathan Keltz Jake Steinberg Guest Star Janet Montgomery Jennie Guest Star Branden Williams Branden Williams Guest Star Johnny Galecki Johnny Galecki Guest Star Andrew Dice Clay Andrew "Dice" Clay Guest Star Elaine Tan Tammy Guest Star Malea Rose Joy Guest Star Natasa Fontaine Rehab Girl Guest Star Lucas Ellin Jonah Gold Guest Star Serene Branson Reporter Guest Star Jesse Erwin Waiter Guest Star Kayla Compton Monica Guest Star Jason Stuart Doc Hock Guest Star Samantha Basalari Girl Leaving Party Guest Star Mark Wahlberg Executive Producer Stephen Levinson Executive Producer Doug Ellin Executive Producer Denis Biggs Executive Producer Rob Weiss Executive Producer Ally Musika Executive Producer