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 Snoop Dogg Snoop Dogg Guest Star Bob Balaban Doctor Guest Star Rhys Coiro Billy Walsh Guest Star Jen Dede Angela Guest Star Perrey Reeves Mrs. Ari Guest Star Madison Dylan Cindy Guest Star Ryan Eggold Castmate Guest Star Kayla Ewell Amy Guest Star Jozef Fahey Teen Guest Star Ryan Flynn Counter Person Guest Star Austin Graves Skylar Guest Star Brian Grazer Brian Grazer Guest Star Cynthia Harmon Bikini Model Guest Star Carla Jimenez Nurse Guest Star Dave Johnson Guest Star Joshua LeBar Josh Weinstein Guest Star Rex Lee Lloyd Guest Star Shawn McDonald Agent Guest Star Elvis Mitchell Elvis Mitchell Guest Star Steven Montfort James 'JJ' Guest Star Megan Porter Party Girl Guest Star Taylor Tan Hostess Guest Star Cole Williams Five Towns Castmate Guest Star Constance Zimmer Dana Gordon Guest Star Mark Wahlberg Executive Producer Stephen Levinson Executive Producer Doug Ellin Executive Producer Larry Charles Executive Producer