13. Nicole Richie for T-Mobile Sidekick
Actress Nicole Richie arrives at the party for the launch of T-Mobile Sidekick 3 in Los Angeles June 20, 2006.
Note to tech companies: Just because someone is the sidekick to one of the world's most obnoxious untalented celebrities doesn't mean she should be your product's spokesperson. Even if said product is called the Sidekick.
Next page: Ben Stein and Shaq for Comcast