Howard had a super fan, Mandy, and her husband, Gary, who'd come from San Diego, into the studio for a tour. Howard then announced he had a game for Mandy – a game that she agreed to off the air prior to coming up – where he asked her a series of show-related trivia questions for money.
However, Howard also noted that, if Mandy didn't get questions correct, she'd have to get naked and Sal and Richard would also give her "jackhammer pudding pies," which Sal explained involved them dipping their scrotums in pudding and then "jackhammering" Mandy with them.
As Howard went through the articles of clothing Mandy had to remove if she got questions wrong, Gary pointed out that he and Mandy had worked out the details on the phone, and, as she expressed concerned about her body being criticized, everyone in the studio promised not to evaluate her if she ended up topless.
To make Mandy even more comfortable, Howard offered to allow her to keep her panties on no matter what, but Mandy again was hesitant. This brought Ronnie the Limo Driver into the studio to insist Mandy knew she was supposed to get naked for a tour of the studio, and Gary added the only reason he allowed her and her husband into the studio was because she agreed to take off her clothes.
After Mandy and her husband were made to leave the studio because they wouldn't cooperate, Howard asked if anyone wanted to be tea-bagged by Richard and Sal, for the $500 prize money, but there were no takers. Richard said, though, that, if he were given all the money he'd let Sal give him a "jackhammer pudding pie," and Sal agreed to do it. Sal then gave Richard a series of "jackhammer pudding pies," while Richard, who couldn't talk clearly because he didn't want to open his mouth since there was pudding all around it, asked for a napkin so he could clean himself off.
Howard then took a number of calls, including one from Yucko the Clown, who begged him to end the segment because they thought it was "too gay."