When Should Jon Hamm Have Won His Emmy?

In his time playing angst-ridden adman Don Draper on AMC’s Mad Men, Jon Hamm has become one of Emmy’s most notorious bridesmaids: seven nominations for Outstanding Lead Actor in a Drama Series; zero wins.

Hamm scored his eighth nomination last week for Mad Men’s final episodes, and it seems unthinkable that he could finish his run as Don Draper without taking home a single Emmy. But then again, he was up against some stiff competition during this modern Golden Age of TV we’re experiencing — so is his lack of an Emmy really such a snub?

That’s what we’re here to answer: We’re looking back at each year Hamm was nominated for Mad Men, evaluating his performance that season, and judging it against the actor who did win that year. Let’s find out how many Emmys Hamm should rightfully have on his mantel by now.

Season 1

Hamm’s episode: “The Wheel”
Winner: Bryan Cranston, Breaking Bad, “Pilot”

First, we should note: Emmy acting nominees are judged on a single episode they submit from that season, so we’ll be judging Hamm and his competitors based on those episodes alone. And Hamm goes up against a very tough competitor right away with his AMC channel-mate: Breaking Bad star Bryan Cranston.

It seems Hamm picked the right episode to submit: The Season 1 finale “The Wheel” features his mesmerizing, instant-classic pitch for the Kodak Carousel slide projector that brought Harry Crane to tears. But it’s also tough to argue with Walter White frantically piloting an RV through the New Mexico desert in his tighty-whiteys. These are two mammoth performances in their embryonic stages; it’s just a shame we can only choose one.

Should Hamm Have Won? It’s a close call, but we’ll say no. Cranston deserved to draw first blood.

Related: The 24 Best ‘Mad Men’ Scenes, Ranked

Season 2

Hamm’s episode: “The Mountain King”
Winner: Bryan Cranston, Breaking Bad, “Phoenix”

It’s déjà vu all over again, with Hamm competing with Cranston for the Emmy. And as much as we’d like to even the score between these two, we can’t. Season 2 was probably the weakest one for Mad Men, and Hamm’s episode, “The Mountain King,” found Don lounging in California with Anna Draper, far away from the action at Sterling Cooper. In retrospect, episodes like “The New Girl” and “Meditations in an Emergency” might’ve been stronger choices for Hamm.

Meanwhile, Cranston submitted “Phoenix,” where Walt watches Jesse’s girlfriend Jane choke to death on her own vomit — and maybe takes his biggest step toward becoming Heisenberg. Enough said.

Should Hamm Have Won? Nope. Cranston makes it two-for-two.

Video: One for the Road: The ‘Mad Men’ Cast Remembers Their Last Day on Set

Season 3

Hamm’s episode: “The Gypsy and the Hobo”
Winner: Bryan Cranston, Breaking Bad, “Full Measure”

OK, this is getting ridiculous: For the third straight year, Cranston tops Hamm for the big prize. (Hamm must’ve been rooting for Gus Fring to put a bullet in Walter White’s bald head by this point.) “The Gypsy and the Hobo” was certainly a great episode choice for Hamm; that’s the one where Don’s wife Betty confronts him about his secret identity as Dick Whitman, leading to Don breaking down and confessing his sins to her.

Cranston’s episode, the Season 3 finale “Full Measure,” sees Walter White staring down Gus Fring in the high desert and ordering Jesse to execute rival meth cook Gale. As with Season 1, we’re faced with two fantastic choices here. In fact, it’s so close that we’re going to defer to the Emmy voters and stick with the reigning champ.

Should Hamm Have Won? Sorry, Jon. It’s a three-peat for Cranston.

Photos: ‘Mad Men’: What the Cast Is Doing Next

Season 4

Hamm’s episode: “The Suitcase”
Winner: Kyle Chandler, Friday Night Lights, “Always”

Finally, a lucky break for Hamm: Breaking Bad didn’t qualify for the 2011 Emmys (it was in between seasons that year), so Hamm didn’t have to suffer through losing to Cranston for a fourth straight time. But he did lose anyway, to Kyle Chandler’s swan song as Coach Eric Taylor in the final season of Friday Night Lights.

We can’t say a bad thing about FNL or Chandler’s performance in the series finale, “Always.” (“Will you take me to Philadelphia with you, please?” will always break our hearts in the best way.) But on the other hand: “The Suitcase.” This pivotal Mad Men episode, which saw Don and his protégé Peggy bond during an all-night work session, is simply one of the best episodes in TV history — and it’s Hamm’s best work in the series, too. This is his year. Finally.

Should Hamm Have Won? Yes! Chandler was great. Hamm was greater.

Related: ‘Mad Men’: The 11 Key Moments in Don and Peggy’s Relationship

Season 5

Hamm’s episode: “The Other Woman”
Winner: Damian Lewis, Homeland, “Marine One”

So by our calculations, Hamm should’ve been looking for his second Emmy when he went up against Bryan Cranston one more time at the 2012 Emmys. And he had one hell of a scene to bolster his case: the scene where Peggy quits SCDP and says goodbye to Don in “The Other Woman.” (Elisabeth Moss probably should’ve won for that scene, too.)

But they all fell victim to a Homeland sweep: Showtime’s terrorist drama cleaned up in its first season with four major awards, including best actor in a drama for Damian Lewis, as Marine-turned-sleeper agent Nicholas Brody. Lewis’s performance in the finale, “Marine One,” was fever-pitched, with Brody nearly detonating an explosive vest to kill the Vice President. But was it better than Don tenderly kissing Peggy’s hand goodbye? Nope.

Should Hamm Have Won? Yeah, he should’ve. We might hesitate if Cranston had won (“Crawl Space”!), but against Lewis? Hamm all the way.

Video: Mad Mementos: The ‘Mad Men’ Cast Reveals What They Kept From the Set

Season 6

Hamm’s episode: “In Care Of”
Winner: Jeff Daniels, The Newsroom, “We Just Decided To”

In our alternate Emmys timeline, Hamm has two trophies heading into the 2013 ceremony — but he’s not done yet! In fact, he submits some of his finest work yet in the Season 6 finale, “In Care Of,” as Don’s alpha-male mask drops during a pitch to Hershey’s and he tells the clients about his dirt-poor childhood spent in a whorehouse. It’s Don Draper at his most vulnerable… and Jon Hamm at his best.

He didn’t win, though; Jeff Daniels swooped in and snatched the statuette away from Hamm and Cranston with his work as news anchor Will McAvoy in the pilot of HBO’s The Newsroom. That show certainly went off the rails, and quickly, but the pilot is good, and Daniels is good in it — particularly his showcase rant about what’s wrong with America. As the years go by, though, and we start to forget why we ever liked The Newsroom, this looks more and more like a mistake. Hamm deserved to hear his name called. Again.

Should Hamm Have Won? Yes, he should’ve been collecting his third Emmy, equaling Cranston at that point. Take that, Heisenberg!

Related: ‘Mad Men’ Creator Matthew Weiner Answers Your Burning Finale Questions

Season 7a

Hamm’s episode: “The Strategy”
Winner: Bryan Cranston, Breaking Bad, “Ozymandias”

AMC split the final season of Mad Men into two halves, giving Hamm two more chances to snag that elusive Emmy. But he ran into an absolute buzzsaw in Cranston and Breaking Bad’s final episodes. Bad’s popularity was through the roof at that point, and there was no way Cranston was walking away empty-handed.

We love the episode Hamm submitted, with Don and Peggy’s bittersweet slow dance to Sinatra’s “My Way.” But “Ozymandias” was a flat-out masterpiece, and Cranston’s performance in it, with Walt desperately clinging to the shreds of his former life as it falls to pieces, was indelibly great. He ordered Emmy voters to “say my name” one more time… and they obliged.

Should Hamm Have Won? Nah, Cranston earned the right to go out on top.

So now we’re left with Hamm’s final seven episodes of Mad Men, and his final shot to win the Emmy as Don Draper. We’re not sure what episode he’ll submit, but we’d put money on it being “Person to Person,” the series finale that saw Don experience an emotional epiphany at a California spiritual retreat and finally find some inner peace. But will Hamm find his way up to the Emmy podium?

We’re betting yes, if only because voters are keenly aware of Hamm’s bridesmaid status and would like to send him off a winner to honor the full breadth of his work on the series. Also: No Cranston this year! Breaking Bad is off the air, so Hamm only has to contend with nominees like Kevin Spacey (House of Cards), along with former winners Kyle Chandler (Bloodline) and Jeff Daniels (The Newsroom).

But frankly, we don’t think any of them stand a chance. It’s Mad Men’s final time at bat, and Hamm’s work in the finale was solid enough to bring home the win. Finally, at long last, Hamm will be clutching the Emmy he’s sought for so long. We just wish it wasn’t his first.

The 67th Emmy Awards air Sept. 20 at 8 p.m. on Fox.