Harry Connick Jr.’s head is going to shine like the top of the Chrysler building. The Grammy and Emmy winner is stepping into the suave shoes of Oliver “Daddy” Warbucks in Annie Live!, airing on NBC December 2, and Vanity Fair has the exclusive first look at his transformation from jazz crooner into bald billionaire. Connick leads a stellar cast that includes Taraji P. Henson as the ruthless Miss Hannigan, reunites Unbreakable Kimmy Schmidt’s Jane Krakowski and Tituss Burgess as con-couple Rooster and Lily, and newcomer Celina Smith as lil’ orphan Annie.
Fans of the 1973 Tony-winning musical wondered if Connick Jr. would shear his luscious brown locks to play the canonically bald Warbucks, originated by Reid Shelton on Broadway and played by Albert Finney, Victor Garber, and Jamie Foxx in various movie adaptations. Connick, too, knew he had to go hairless for the role. “That character has been around since I think the ’20s,” he said over the phone to V.F. “That’s who Daddy Warbucks is.” Connick, who starts rehearsals for Annie in early November, chatted with V.F. about bald caps, billionaires, and the timeliness of a musical that’s all about hope.