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 Debi Mazar Shauna Guest Star Perrey Reeves Mrs. Ari Guest Star Constance Zimmer Dana Gordon Guest Star Paul Ben-Victor Allen Grey Guest Star Hugh Hefner Himself Guest Star Ralph Macchio Himself Guest Star Danny Masterson Himself Guest Star Pauly Shore Himself Guest Star Chene Lawson Jennifer Guest Star Paul Herman Marvin Guest Star Patty McCormack Realtor Guest Star Kate Albrecht Christy Guest Star Amanda Tepe Mac Assistant Manager Guest Star Rex Lee Lloyd Guest Star Colleen McGrann Ralph's Wife Guest Star Yorgo Constantine VIP Guest List Guy Guest Star Stephen Keys Guard Guest Star Stacy Fuson Girl at PJ Party Guest Star Daniel Booko Frat Guy Guest Star Adam Green Frat Guy Guest Star Holly Madison Playmate Guest Star Bridget Marquardt Playmate Guest Star Kendra Wilkinson Playmate Guest Star Jonathan Baker Himself Guest Star Mike Masland Typical Drunk Bro Guest Star Mark Wahlberg Executive Producer Stephen Levinson Executive Producer Doug Ellin Executive Producer Larry Charles Executive Producer