Saturday Night Live

Britney Spears (1)

Aired May 13, 2000 · 11:30 PM ET · 1h 05m

Live From New York, it's...Ana Gasteyer Sketches include: ""A Message From Giuliani"", ""Gap Fat"", ""Morning Latte"", ""Boston Teens' Field Trip"", ""TV Funhouse: The Ambiguously Gay Duo"", ""Clinton Scandal Commemorative Plates"", ""Homeless Woodrow Meets Britney Spears"", ""The DeMarco Brothers"", ""DeAndra Wells' Comeback Tour"", and ""Uncle Jemima's Mash Liquor"" The host/musical guest sings: ""Oops...I Did It Again"" and ""Don't Let Me Be The Last To Know""