Date: December 1985

The Moment: In 1985, as the holiday shopping season kicked into full gear, commercials for Swatch started appearing in New York City, featuring an unlikely celebrity endorsement: the Fat Boys, performing the song they'd recorded for the occasion, "Swatch Watch Presents A Merry Christmas."

The Impact: After a Swatch-sponsored tour with Run-DMC, Kurtis Blow, and Whodini, the endorsement of the watch-slingers—made possible by the Fat Boys' manager Charlie Stettler, a Swiss national—became one of the most successful cool-kid ad campaigns of all time, and shot the Fat Boys into the forefront of hip-hop as one of its most charismatic, charming, and irresistible acts.

The Upshot: The Fat Boys continued to appear in movies and TV shows (Disorderlies, an episode of "Miami Vice") and made some classic records along the way. More importantly, they proved that rappers were as capable of being a celebrity spokesperson as any other stripe, and thus, paved the way for so many of the multi-million dollar deals we know all too well to come.