Guess the Tranny
Originally aired 06/09/2009, Howard welcomed three women to the studio to play Guess the Tranny. The first woman, Amy, was wearing a Wonder Woman outfit and stumped Howard: "Your voice is really deep. But your breasts are really nice. If you're a guy, I'm gonna shit my pants...I'm literally gonna move my bowels on this chair." The next girl said her name was Vaniity, and Gary immediately flagged her gender as suspect: "She's so hot, but there's something going on with that voice."The final contestant, Sasha, had a more feminine sounding voice. Artie had one question: "Can we see all of you throw out the first pitch at a Mets game?" Everyone then registered their votes. Robin picked Amy: "She seems to me to be the kind of woman who'd be in porn...there's all kinds of wacky stuff going on." Fred also picked Amy, but Gary went with Vaniity. Benjy agreed, telling Vaniity: "You're the hottest but you're also a guy."
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