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The Smoking Jacket is the sixth episode of Curb Your Enthusiasm Season 5. It is the forty-sixth episode overall.


Larry's cousin Andy David comes for a visit and takes Cheryl David's copy of Us magazine into the bathroom with him. Larry throws the magazine out in disgust. The next day, Cheryl is upset when she learns Larry threw it out, since she wrote an important phone number on it. Jeff Greene is invited to the Playboy Mansion, but Larry says he can't go because he knows Cheryl would disapprove and she is already angry with him over the magazine. Jeff argues the reverse is true: since Cheryl is already angry with him, going to the Playboy Mansion won't make a difference. He calls this the "double transgression theory" (seemingly ignorant of the fact that "double transgression" is a popular euphemism for anal rape).

Larry's father sends Andy his smoking jacket as a Christmas present. Larry is convinced that his increasingly senile father meant to give the jacket to him, having promised it to him long ago, but Andy refuses to give it up. Larry negotiates for the jacket in exchange for bringing Andy on the Playboy Mansion visit.

Larry pays frequent hospital visits to Richard Lewis's comatose cousin Louis Lewis, hoping he will die soon so that Richard can have his kidney and Larry won't have to donate his own. The doctor says there is no telling how much longer Louis will live, so after he leaves Larry begins fiddling with the wires to Louis's life support. The young boy in the adjoining bed catches him and threatens to tell everyone that Larry tried to pull the plug on Louis unless he fulfills the wish which the Make a Wish Foundation rejected: To see a naked woman. Knowing Cheryl would never agree to expose herself to an underage boy, Larry decides to bring him to the Playboy Mansion.

The girls at the Playboy Mansion are more prudish than Larry thought, covering up their private parts and running away screaming the instant they spot a male in the pool area. Andy has better luck, scoring a date with a Playboy model. Larry meets Hugh Hefner, who is wearing a smoking jacket, and tells him that he has the same one. Hefner is skeptical since the jacket is a custom-made Roselli, so Larry brings it in. Hefner says it is not a real Roselli but is impressed by its quality. Larry lets him try it on. Hefner takes a long bathroom trip and then takes off the jacket, but Larry does not want it now that it has been in the bathroom, so he swaps it with Hefner's Roselli when no one is looking.

While looking for another way to fulfill the terminal boy's wish, Larry accidentally walks in on Andy having sex with the Playboy model, to the boy's delight.

Larry's father complains that his smoking jacket has been stolen, having forgotten that he mailed it to Andy. Larry gives him the Roselli, but he recognizes it is different, calling it a knock-off, and demands his real jacket back. Larry tells Hefner that their jackets got mixed up, but Hefner cannot tell the difference and insists the jacket he now has is the real Roselli. Larry calls in his favor for showing the boy a naked woman, and the boy uses his wish with Make a Wish to ask for Hugh Hefner's smoking jacket.