4. Celebrity: Common
Clothing line: Soji Hats
Launch date: 2007
Fail date: 2009
Reasons for the fail: We’re gonna go with making Jeremy Piven your celebrity spokesmodel. The line was a good idea in theory, since Common has been rocking newsboys forever (remember the tie-dyed knit versions of the Erykah Badu era?), but even partnering with established Italian hatmakers La Coppola Storta couldn’t erase the vision of Ari Gold in an applejack cap. Still makes us shudder.