17. Debbie Downer: Happiest Place on Earth?
Original Airdate: May 1st, 2004
In her autobiography, Rachel Dratch explained that her Debbie Downer character was inspired by a trip abroad: When she informed a stranger that she was from New York City, they replied, "So were you there for 9-11?" She and co-writer Paula Pell introduced the character in a Disney World sketch in 2004 – the first of seven appearances – and it was so funny that it induced some of the best character-breaking crack-ups in SNL history. Guest host Lindsay Lohan, who was 16, remembered laughing so many times in rehearsal that she was afraid of being fired. When the sketch went live, the line that broke everyone was, "It's official: I can't have children" – at which point, Horatio Sanz was literally wiping away tears with his Mickey Mouse waffle.