It seems like The Canon could always use more comedies and musicals for consideration, and in light of the recent Sound of Music episode I submit Victor Victoria. It's an utterly hilarious Blake Edwards film and a fantastic showcase for Julie Andrews. Glee's got nothing on "Le Jazz Hot". All the supporting players are delightful, particularly Lesley Anne Warren as Norma Cassidy and the waiter who steals every scene he's in. The social politics as explored via gender-bending and homosexuality bear mentioning given that this was made in 1982.
Here's hoping this pops up in a future episode, but even if it doesn't than anyone reading this who has never seen Victor Victoria should definitely check it out. It's a real treat!