Judge Sullivan is the judge Jude clerks for in Washington, D.C., after law school. Harold urges Jude to apply for the position and even serves as a reference. During Jude’s interview with Judge Sullivan, the judge asks Jude to sing a song for him (he’s somehow heard that Jude is a talented singer) that says something about Jude’s character. Jude thinks he’s failed the interview, but Judge Sullivan ends up hiring him.