Family Guy

S6E2: Movin' Out (Brian's Song)

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He's a... He's a failed writer who just decides that, "Oh, I'm going to have a big last hurrah in Las Vegas." And then he meets a whore and pays her a bunch of money to stay with him, and have sex with him while he murders himself slowly. And, you know, she's game for it, but she catches feelings midway through and the whole thing changes.