Question: What TV show's fifth season did the man who has earned more number-one albums than any other artist in US jazz chart history guest star on?
Sentence (from "Marry Me a Little, Marry Me a Little More"): Guest stars in "Marry Me a Little, Marry Me a Little More" include Harry Connick Jr., Katie Couric, Judith Ivey, and Debbie Reynolds.
Relevant evidence: Yes