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Matthew McConaughey Ed 'Eddie' Pekurny Woody Harrelson Ray Pekurny Sally Kirkland Jeanette Jenna Elfman Shari Martin Landau Al Ellen DeGeneres Cynthia Topping Rob Reiner Mr. Whitaker Dennis Hopper Henry 'Hank' Pekurny Elizabeth Hurley Jill Adam Goldberg John Viveka Davis Marcia Clint Howard Ken Geoffrey Blake Keith Gail Boggs Wife Jenna Byrne Felicia Greg Sestero Roach RuPaul RuPaul Merrin Dungey Ms. Seaver Ian Gomez McIlvaine Gavin Grazer Clint Chris Hogan Paul Arianna Huffington Panel Member Larry Jenkins Husband Wendle Josepher Rita Scott LaRose Desipio John Livingston Terry Mitzi McCall Fig Lady Jim Meskimen Dr. Geller Don Most Benson Rick Overton Barry James Ritz Tad Rusty Schwimmer Alice Steven Shenbaum Jack Gedde Watanabe Greg Steve Kehela Reporter Googy Gress Reporter Jo McGinley Tracy John Pirruccello Kevin Charles Arthur Berg Party Goer Anthony Jensen Party Goer Sommer Garcia College Girl Jennifer Elise Cox College Girl Alexandra Holden College Girl Mark Wheeler Bartender Anna Karin Snapple Girl George Plimpton Panel Member Michael Moore Panel Member Merrill Markoe Panel Member Bill Maher Bill Maher Jay Leno Jay Leno Sonia Bhalla Ticket Taker Joe Bellan Lou Diane Amos Autograph Mom Wade Robson Teenage Boy Andy Arness Groupie (uncredited) Cyndi Pass Cassie J. Anthony Pena Con-Ed Guy (uncredited) Carl Solomon Ed Groupie (uncredited) Bob Sarlatte Motorcycle Cop T.J. Thyne Frat Gut Harry Shearer Moderator