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Directed by: David Steinberg
First aired: November 6, 2005
Synopsis: Larry makes two wishes come true, and swaps smoking jackets with an icon.
Guest Starring: Hugh Hefner (Himself) Richard Kind (Andy) Gary Player (Himself) Shelley Berman (Nat David) Bobbi Sue Luther (Bobbi Sue) Holly Madison (Holly) Kendra Wilkinson (Kendra) Bridget Marquardt (Bridget)
Featuring: Trisha Debski (Social Worker) Bobbi Sue Luther (Playmate) Holly Madison (Herself) Bridget Marquardt (Herself) James Pickens, Jr. (Doctor) Grant Rosenmeyer (Wilson) Bill Saluga (Louis Lewis) Kendra Wilkinson (Herself) Rhett the Dog (Oscar)
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