20. Olivia Palermo, The City (MTV)
Olivia Palermo was probably the most entertaining part of The City. Supposed star Whitney Port was predictably bland, but socialite Palermo spiced things up with her snobby comments and, um, unorthodox job skills.
She constantly thwarted Port’s efforts to make it in the fashion industry and did all she could to keep her designs out of Elle magazine. Post-MTV, Palermo launched a lifestyle website and is adored by legions of style bloggers and Tumblr teens. A return to reality TV is totally the next step.