Howard welcomed Mark to the studio to play "Beat the Booey," as well as Gabrielle, a 21-year-old Long Island bartender who will get naked if Mark loses. Gabrielle reported that she was bi-sexual, and in fact had a girlfriend at 16 – at least 8 months before she was ever with a guy. Howard asked what women did better than men, and Gabrielle said oral sex: "Be flat with your tongue. Not pointy." Gary was confused: "[I've] learned nothing." Howard then told the guys to put their hands on their buzzers and prepare for the questions:
How many children does Howard have? Gary: 3.
Name Howard's first wife. Gary: Allison.
Where did Howard's mother take his temperature? Mark correctly answered with "rectum."
What breed is Howard's current dog? Gary: Bulldog.
Who won the boxing match between Stuttering John and Cabbie? Mark: John.
On what sitcom did Artie co-star before joining the show? Mark: The Norm Show.
Who does JD hate most? Gary: Jared Fox.
In what game to contestants match their wits against Fred? Mark: Win Fred's Money.
What is Scott the Engineer's last name? Mark: Salem.
Which staffer is usually welcomed to the studio with techno music? Gary: JD.
What was the name of the Website Jon Hein sold to TV Guide? Gary: Jump The Shark.
Which former Hell's Angel hosts a show on Howard101? Gary: Chuck Zito.
Ivy Supersonic recently dated which staffer? Gary: Benjy.
In 2006, which wife of a rock legend let Howard feel her boobs? Neither contestant knew it was Sharon Osbourne.
Which porn star was the prize in the first Mexican Delivery Game? Neither contestant knew it was Savanna Samson.
Which advertiser did Howard mention on his most recent Letterman appearance? Neither contestant knew it was No-Doro.
Which game show host confessed to Howard that he suffered from OCD? Gary: Howie Mandel.
What famous star made a cameo appearance in "Private Parts?" Gary: Ozzy Osbourne.
Crazy Alice is half-black and half what? Mark: Italian.
Robin infamously confessed to masturbating with what types of food? Mark: Meat and vegetables.
Which staffer caught hell for posing his daughter in Howard's chair? Gary: Doug Goodstein.
When is Artie's birthday? Neither contestant knew it was October 11th.
How old was Kenneth Keith Kallenbach when he died? Neither contestant knew he was 39.
Which Stern show roast comedian once had sex with a cat? Gary: Colin Quinn.
Katie Lee Joel brought in what food for Artie? Neither contestant knew it was chocolate chip cookies.
On what talk show did Howard's mother make an appearance? Gary: The David Brenner Show.
What kind of motorcycle is Fred's favorite? Mark: Triumph.
What publisher released Quivers: A Life? Gary: Regan Books.
Larry King once called Howard the __?__ for the ugly team? Neither contestant knew the missing word was quarterback.
Gary won! Howard then dropped the curtain to reveal a nude Gabrielle and asked her which person in the studio creeped her out the most. Gabrielle looked around at all the eyes on her and decided she had too many options: "Hmm...it's hard to tell."