Howard then welcomed several men for The Prettiest Penis Contest. The first contestant was 78-years-old and fully nude. George said the guy's penis was "a well-balanced penis, but it lacks a little volume." The second contestant, Maury, whipped his out as well – after a little "chubbing up" - and George was unimpressed. George was more excited by the next contestant, Mike, who also had a "well-balanced" penis.
The fourth contestant, Go-Go Boy, said he was a try-sexual ("I try anything") and George loved his package: "It's beautiful. It could use a little bit of a workout." The next contestant said he was "one of the original jackasses," and, despite his best efforts, ended up having his "entry" dismissed. The next guy had a circumcised penis but used a device (Fred called it a "penis restoration cone") to regenerate his foreskin. George was impressed ("Good for you!") but gave the award and the $500 prize to Mike, the third guy.