Bored to Death (2009)

S1E6 The Case of the Beautiful Blackmailer

Jonathan is tasked with recovering a sex tape that a female escort is using to blackmail a married man from New Jersey. Accompanied by Ray and George, he finds himself in a motel room facing the escort, who then tries to extort him as well. With Ray and George both heavily under the influence, will they be able to rescue Jonathan before her furious brother gets the chance to settle the score?