Best known for: Don Draper, Mad Men (AMC)
Weirdest role: Jackson, The Trouble With Normal (2000)
Early on in his career, Hamm could often be seen as "the hot guest star" in all of your older sister's favorite TV shows. He made characters and audiences swoon in guest spots on Gilmore Girls, Ally McBeal, and Charmed before landing in the bourbon-damp shoes of Don Draper. In the midst of this square-jawed yeoman's work, Hamm did a stint on a show best described as Sex and the City, except with four male conspiracy nuts instead of shopaholics. The short lived show, The Trouble with Normal, had a cast that reads like a latter-day TV fantasy team. In addition to Hamm's work in the pilot, John Cryer of Two and a Half Men, Jim Beaver of Justified and Deadwood, and David Krumholz of Numb3rs (and pretty much everything else) regularly appeared on the short-lived show.