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 Perrey Reeves Mrs. Ari Guest Star Rex Lee Lloyd Guest Star Gary Cole Andrew Klein Guest Star Emmanuelle Chriqui Sloan McQuewick Guest Star Jordan Belfi Adam Davies Guest Star Nora Dunn Dr. Marcus Guest Star Jana Kramer Brooke Manning Guest Star Nicky Whelan Air Hostess Guest Star Terasa Livingstone Stewardess Guest Star Beverly D'Angelo Barbara Miller Guest Star Jamie-Lynn Sigler Jamie-Lynn Sigler Guest Star William Fichtner Phil Yagoda Guest Star Bono Bono Guest Star Matt Damon Matt Damon Guest Star LeBron James LeBron James Guest Star Malcolm McDowell Terrance McQuewick Guest Star Preston Davis Jeff Guest Star Michael Roemer Ari's Lawyer Guest Star Hollis Doherty Airline Lady Guest Star Olga Fonda Sales Girl Guest Star Jeff Harlan Jesse Guest Star Doug Ellin Director Guest Star, Executive Producer Sandra Milliner Woman Guest Star Daniel Kash Agent 1 Guest Star Brian Johnson Agent 2 Guest Star Elizabeth Wachsberg Agent 3 Guest Star Matthew Pocock Pilot Guest Star Jay Mattson Co-Pilot Guest Star Rich Paul Rich Paul Guest Star Marc Joubert Marc Joubert Guest Star Jim Edmonds Jim Edmonds Guest Star Kenny Dichter Kenny Dichter Guest Star Mark Wahlberg Executive Producer Stephen Levinson Executive Producer Larry Charles Executive Producer