Jon Hamm just wrapped his role as Don Draper on Mad Men after an incredible eight-year run. He was nominated for Outstanding Leading Actor in a Drama Series for every single season, but he (quite famously) has never won. He has lost to Bryan Cranston four times, and to his fellow 2015 nominees. The field for Drama Actor this year is tough: Emmy favorites Kyle Chandler, Jeff Daniels, and Kevin Spacey are nominated, Daniels and Spacey having already won for the same roles. Nominee Bob Odenkirk is also getting big buzz for the win — he won the Critics' Choice Television Award, and will likely be lauded for his impressive jump from supporting player to leading actor.
With Leading Actor a particularly tight race, it is unlikely that Hamm will win, particularly because the Emmys has been consistently undermining him since the beginning of Mad Men. There is, however, an exciting loophole that might finally give Hamm the Emmy win he deserves. In addition to his nomination for Mad Men, he is up for Outstanding Guest Actor in a Comedy Series for his hilarious turn as charismatic cult leader Richard Wayne Gary Wayne on Unbreakable Kimmy Schmidt.
Like he did as one of Liz Lemon's boyfriends on 30 Rock, Hamm brilliantly used his handsomeness for humor to the point of self-parody. He satirized charismatic cult leaders by being at once convincing and extremely dopey.
The competition for Guest Actor in a Comedy Series is smaller, and Hamm undoubtedly has the biggest role. The other nominees are Mel Brooks for The Comedians (in which he played himself), Bradley Whitford for Transparent, Paul Giamatti for Inside Amy Schumer, and Louis CK and Bill Hader for their hosting stints on Saturday Night Live. Hamm, without a doubt, contributed the most to his respective show, in both screen time and pure hilarity. For Kimmy Schmidt, and then the added bonus of honoring his run on Mad Men, Hamm finally has a shot.
Even if it's for the wrong show, it's at least something, right?