Stars like Will Ferrell, Matt Damon, Oprah Winfrey and Kermit the Frog all stopped by
Played: Steven Austin in season 5's "Brooklyn Without Limits"
If it hadn't been for the "Alfie and Abner" sketch, Slattery might have stolen the title of Funniest "Mad Men" Guest Star on "30 Rock" away from his buddy Hamm. As a deranged, astoundingly unqualified independent congressional candidate Jack backed to protect the NBC/KableTown merger, Slattery adopted a Rhode Island accent, appeared in a baby costume — as part of a larger fetish that also saw him emerging from a woman's legs in a campaign ad — spouted anti-minority and pro-moon colony rhetoric, and generally made the biggest fool of himself possible. And if you want to give him bonus points for beating Hamm to the blackface punch (albeit on a different show), by all means.
- Alan Sepinwall