Jack has his sights set on conservative talk show host Dr. Anne Childs, but he finds plenty of time to bed a bevy of beauties as he challenges the uptight Doctor to see how fun sex can be.
John Leslie
Jack
Bridgette Monet
Dr. Anne Childs
Blair Harris
Lenny
Nicole Black
Gloria
David Cannon
Miles
Ann Pierce
Maid
Paul Wright
Louise Jackson
Lynn Francis
Taller Threesome Girl
Cara Lott
Threesome Girl
James R. Sweeney
Bar Patron Watching TV
Paul Thomas
Piano Player
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Louis C.K.: Oh My God
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Bill Hicks: Sane Man
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Desperate Living
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The Horse's Mouth
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