10 Pivotal Moments in Band/Brand Relationships

3. Pepsi learns the perils of coolness by association

It only took them a decade to nail down the idea, but after Coke’s big pop culture moment in 1971, Pepsi hired the first in a series of musicians as pitchmen. The #1 draft choice was Michael Jackson and the Jackson 5, who in 1984 became the company’s first pop-star spokespeople. They also became the first in a series of embarrassments suffered by Pepsi at the hands of their celebrity ambassadors, when Michael was badly burnt on the set of a commercial. In 1987, Pepsi tapped and then untapped David Bowie after some sexual assault charges popped up. They did the same in 1989 with Madonna, after her controversial video for “Like A Prayer” debuted. Pepsi didn’t quite have the stomach to hang in long enough to get the “cool by association” bump from most of their pop-star pitchmen and in the ’90s went with a series of safe choices like Ray Charles and Aretha Franklin.

By the 2000s, Pepsi mastered the art of managing the volatile spokesperson and made it successfully through runs with Britney Spears, Beyoncé, and Pink. They even managed to stand by Kanye West after his infamous “George Bush does not care about black people” verbal bomb at a Hurricane Katrina fundraiser.