Howard announced that he'll be on an upcoming cover of Entertainment Weekly, and that one of the magazine's reporters, Josh, was sitting in the studio for the next segment. As David Spade made his way in for the interview, Howard recalled that he thinks the best cover he's ever done was the last time he appeared on the front of Entertainment Weekly holding a baby with the headline "Who's Afraid of Howard Stern?" written on it. After Howard wondered what parent would let their baby to be on the cover of any magazine, Robin pointed out that David was growing facial hair. David responded that he hasn't been working on television lately, so he's been "experimenting" with his look. When Robin noted that his moustache made him look "dirty," David thanked her.
Howard asked how David gets away with the jokes he tells on "The Showbiz Show" that are at the expense of his celebrity friends. David acknowledged that he's upset some of his friends with the jokes he's done on the show, including one that bothered Brad Pitt, which led Howard to wonder how they know each other. David told Howard that he met Brad on the set of "Saturday Night Live" shortly after Brad had filmed "Thelma and Louise." David went on to explain that Brad wasn't very famous at that point, and that Brad wanted him to meet some of his family members, who he said were fans of "Tommy Boy." David added that he and Brad have kept in touch ever since. Howard pointed out that he considers David to be a B-List celebrity, so he found it funny that he'll hang out with someone more famous than him – namely, Brad Pitt – but would never be friends with a C-Lister himself. When Artie noted that wasn't true because he's friends with David, Howard told Artie that he's not a C-List star and that he might not even be on the alphabet.
Artie commented that David originally asked him to be in his new movie, "Benchwarmers," but that the role ended up going to Jon Heder of "Napoleon Dynamite" fame instead. Although David first claimed that he made the decision to give the job to Jon because he didn't want Artie to have another breakdown like he did while he filmed "Beer League" last summer, he then admitted that he was actually told by the movie's producers that the teaming of him and Artie wouldn't bring in $100 million at the box office. David went on to say that he's being flown around the country for his current promotional tour on a private jet provided by the movie studio of "Benchwarmers." When Howard noted that he thought David should try to get a woman to fly with him on the private plane as a way to impress her, David replied that there isn't enough room for additional passengers on the jet.
Howard asked David if he's dating anyone and he said he recently got out of a relationship with a woman his age, which is a figure he noted he doesn't reveal. Gary then came into the studio and reported that, while looking for David age on IMDB.com, he read that David allegedly has a tattoo of Calvin from the Calvin and Hobbes comic strip. David responded that he does, in fact, have the tattoo, and that Sean Penn gave it to him. David explained that he needed a segment for "Saturday Night Live" at the time, and he decided that recording Sean inking him would fill that void. David added that he chose the Calvin tattoo because it was the easiest one for Sean to draw, and that he now regrets going through with the bit.
Howard mentioned that David used to be involved with Kristy Swanson, so he wondered what he thought about her relationship with her former partner from "Skating with Celebrities," a man who Howard noted was married when they met. David admitted that the news wasn't "super shocking" to him, explaining that Kristy wasn't the most stable person during their time together, and that was what led to their breakup. David went on to say that he hasn't ruled out the possibility of getting married, but that he'd rather remain single than get married just for the sake of doing so.
While Howard was talking about how he and David have hung out socially in the past, he remembered a time at a Grammy party when they saw Christina Aguilera. Howard mentioned that he approached Christina, whom he admitted he didn't know personally, and introduced her to David. However, Howard noted that David "struck out" with his opportunity to get anywhere with Christina, especially because David asked her what she was doing at the Grammy ceremony when she had just won a few awards that night. David admitted the story was true, and added that he recently saw Christina and her husband at another party, and that Ellen DeGeneres, who he said didn't know Christina was married, tried to set them up, only to be told that she wasn't available.
David said that he watched "Benchwarmers" with a test audience last week, and that it seemed to get a good response from the crowd. David went on to predict that the movie will do well in the box office, although he noted that a few other potentially big movies open at the same time. David then commented that one of the sketches on Thursday's premiere of "The Showbiz Show" involves him wearing blackface and hitting the streets to see if it's more difficult to be an African American than it is a Caucasian. David reported, though, that most of the people he encountered while in blackface recognized him, so he didn't find much of a difference being a member of a different race.
David brought up that he does corporate functions whenever he can, noting that, on average, he gets $100,000 for each appearance. After Artie recalled that he once got paid $5,000 by Kodak just for briefly appearing at a function where he had to pretend to be Chris Farley, David mentioned that he'll be on "Late Show" tonight. David admitted that he always gets nervous before talking to David Letterman because he's never sure what Dave will want to discuss, so he has to write new material for each appearance he makes. When Howard then asked David if he'd be willing to ride the Sybian before he left, David said he couldn't because he had to go do an interview with the Penny Saver.