5. Holly Madison for Travelocity
For the love of William Shatner, how anyone thought Holly Madison would be a good match for a travel website is beyond me. Madison, best known as the former plaything of Playboy principal Hugh Hefner, represented Travelocity in a series of strange ads back in 2009. Most memorably, she pretended to marry a garden gnome. (It's evidently the site's mascot -- or something. Search me.)
Apologies in advance, but it has to be said: At least we know Holly's perfectly comfortable pretending to love a brittle old dude for money.
Next page: Verne Troyer for Klegg