Howard noted that Vinnie has provided several memorable moments to the show, and the first clip he played was of Vinnie's infamous "Debbie Tape," where he videotaped himself for his girlfriend who was living in California at the time.
Following the tape, Howard reported that the visuals of the footage enhance what Vinnie says because he's wearing nothing but underwear at the time.
When Vinnie defended himself, saying that he used to look good in those days, Howard challenged him to back up his claim by allowing the tapes to air on iNDEMAND. The next tapes Howard played were of Vinnie continuously interrupting Ringo Starr, and then challenging Donald Trump about the ratings of "The Apprentice."
Howard proceeded to announce that the best moments Vinnie ever contributed to the show came from the contest that spawned out of his song, "Restless, Restless."
Howard recalled that he obtained a copy of Vinnie singing the song, which he co-wrote with Tom Gesimondo, and that it was so bad that they decided to see if anyone could turn it into something listenable. Howard went on to note that he received more than 1,000 entries for the contest, including submissions from Robert Goulet and William Shatner.
Howard played Robert's performance of the song, as well as that of the contest's winner, Kevin Remuck. Howard thought one of the funniest things to happen during the contest was Vinnie telling Robert Goulet that he had misinterpreted his song.