After mentioning that he has a new book, "The Great Movies Part 2," in stores, Roger again turned his attention to Jon's acting. Roger explained that "The Daily Show" has defined Jon and that he's obviously at ease while hosting it. This led Jon to admit that he used to try too hard when acting and that he wasn't being himself on film. In fact, Jon said that he used to grow a beard before shooting some of his films as a way of trying to come off as a more serious actor. Jon added that viewers will know immediately what to expect of him when they see him on stage for the first time at the Oscars depending on if he's sporting facial hair or not.
Howard revealed that Roger went on a few dates with Oprah during the 1980s and that she credited him for much of her financial success. Roger recalled that he took Oprah to a movie and then to a fast-food restaurant and, while they were dining, she told him she wasn't sure if she wanted to take her show into syndication, or sign a deal with ABC. To help Oprah with her decision, Roger said he wrote on a napkin the salary he was making at the time as co-host of "Siskel & Ebert," and made the necessary adjustments to reflect how much more Oprah would be earning if she syndicated her program. Roger claimed that it was shortly after his presentation that Oprah decided to syndicate. Although they saw each other more than once, Roger admitted that he was never physical with Oprah in any way. After Jon insisted to Howard that he finds Oprah "sexy in person," he denied he was under her spell. Jon went on to say that he never liked Oprah's promotion of Dr. Phil, explaining that he has problems with the way Dr. Phil pretends he can help people in just 30 minutes, while also attaching his name to any product that comes his way. Howard responded that, to him, Dr. Phil agrees to endorse the number of products he does because he didn't come into his money until later on in life. Jon agreed with Howard's assessment, before adding that, to him, Dr. Phil is the new Richard Simmons.
Roger reported that he and Oprah are still good friends and that he recently attended her star-studded 50th birthday party. When Roger mentioned that one of the guests at the party was Natalie Cole, Artie asked Roger if he "pulled the old salary-on-the-napkin trick with her too." After saying he hadn't, Roger noted that the tent Oprah used for her get-together cost more than $2 million alone, which led Howard to comment that he should've held a more elaborate celebration for his 50th birthday. However, Jon assured Howard that his party was great too and that he was positive Oprah's bash didn't have "retarded couples, High Pitch Eric and small hot dogs."