SEASON 1, EPISODE 106 | AIRED ON 12/31/69

Moment #1: The Flash Mob

Over the years, The Oprah Show mastered the art of a good surprise, but TV Guide says the ultimate gotcha moment was a unanimous pick for their staff. During the Season 24 kickoff party on September 10, 2009, Oprah got the surprise of a lifetime. Producers, more than 20,000 audience members and the Black Eyed Peas conspired to pull off a flash mob in the middle of Chicago's Michigan Avenue for an unsuspecting Oprah—who called the moment a "great big dancing love gift."