#12: Dr. Drew Baird (Jon Hamm)
Jon Hamm completely shed his Don Draper reputation to play the ridiculous, ridiculously handsome Dr. Drew, who doesn't understand why everyone doesn't get free muffins at brunch, loses terribly at tennis ("This racquet is a fart!") and eventually replaces his hands with hooks, after losing one to a firework and one to a helicopter. Drew is probably Liz's most absurd boyfriend (yes, even more so than Dennis), but the way both Hamm and the show were willing to skewer his good looks was just one of the many things that helped set all of Liz Lemon's insane relationships apart.

#11: Elisa Padriera (Salma Hayek)
So many different, amazing conflicts emerged when Jack began dating Elisa, from the class differences ("I've never eaten at a restaurant that didn't have a TV in it.") to the culture differences ("What do I call you?" "Puerto Rican." "Wow, that does not sound right.") to Liz awkwardly getting between them ("Lemon, isn't there a slanket somewhere you should be filling with your farts?") Elisa's bizarre traits-- her history as a Black Widow, her Battlestar Galactica T-shirts-- only somehow served to make her feel like a real human being, and though it was never really going to last between them, she somehow seemed a better match for Jack than any of the women who came before or since.

#10: Don Geiss (Rip Torn)
A central figure of the show's early seasons, and killed off when Torn ran into his own real-life troubled, Geiss was the perfect grizzled father figure for Jack to aspire to impress. It made no sense for him to appear on the show as often as he did, but the details of his bizarre family (and second family in Canada, and attic family) and Torn's own knack for one-liners ("Is that the gay guy from Project Runway") made him fit right in. I'll even give him credit for Argus, the peacock Jack inherited after Geiss's death whom he believed contained Geiss's spirit. Why not, right?

#9: Carol Burnett (Matt Damon)
Liz always said Drew looked like a cartoon pilot. Carol was the real deal, and not only was he handsome, but he matched Liz in complete intolerance for the rest of the world, from people who fly in gym clothes ("They think that $300 and a photo ID gives them the right to fly through the air like the guardian owls of legend!”) to the NBA tattoo situation. Of course, those similarities eventually led them to realize they were basically the same person, and the most hilarious and vaguely terrifying showdown on board one of Carol's delayed planes. They might have been a little too much of a match made in heaven, but at least that leaves Carol to find some other cranky woman to love.

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