When Jon Hamm first started hearing the chatter around Mad Men, he noticed a surprising political parallel. The first season of his show was set in 1960, with an episode centered on the infamous Nixon-vs.-Kennedy presidential race. Around the same time it aired, Barack Obama was soaring as a candidate for president. “The new, sexy Democrat challenging the old guard Republican in McCain—it was very much a, Huh, this seems very resonant for some odd reason,” Hamm says on this week’s Little Gold Men (listen or read on below). “It struck people as, Wow, this is happening right in front of our eyes—in fiction and in reality.”

Nearly 17 years later, Hamm is picking up on similar overlap in another election cycle. He’s nominated for two Emmys this year, for both his role as the lead antagonist in the fifth season of Fargo and his mysterious supporting part in The Morning Show. In the former, Hamm plays Roy Tillman, an abusive constitutional sheriff running a North Dakota county by his own rules; the show’s creator, Noah Hawley, has been forthright about Donald Trump inspiring the character. In the latter, he stars as oddball tech billionaire Paul Marks, who takes a seemingly nefarious interest in buying a major news network; the basis for that character, Hamm explains, could cover a range of eccentric contemporary figures.

Hamm’s work in both shows is chilling, if also discomfitingly humane, bringing darkly nuanced characterizations that speak starkly to today’s political culture. It’s the first time Hamm has been Emmy-nominated since his Mad Men run ended—that year, he was also nominated for his hysterical guest appearance on Unbreakable Kimmy Schmidt—but he’s nevertheless kept busy. Over our wide-ranging conversation, the TV veteran gives his frank assessment of the state of the medium, and of the highs and lows that have gotten him to where he is today.

Vanity Fair: These two shows have landed in an interesting moment. In Fargo, you’re playing this Trumpian figure, and in The Morning Show, an Elon Musk-esque tech bro. And we are in an election year where both of those inspirations are quite relevant.

Jon Hamm: Certainly prescient, right? I think sometimes those things happen. Obviously Trump’s been on our radar for some time. And it’s not just Elon Musk, it’s fill in the blank—Zuckerberg, or Bezos, or whichever one of those guys you want to slot into the space. What we did very well was try not to present them in a cartoony way and try not to present them in a tremendously judgmental way. I remember Noah saying, “If I do this right, if I get this balance right, there’s going to be a significant portion of the audience that’s really going to agree with Roy.” And you have to go, “Okay, well, then I can’t play this guy as just a buffoon.”

Fargo presents an elevated reality, to say the least, in the florid language and in the dark humor, and that’s the hallmark of the film. So there is a fable kind of nature to it. But you can’t lean over the edge on that and turn it into a parody, otherwise it doesn’t land. There has to be a sense of reality to it. That was the line that I think we really successfully walked, especially with Roy. There was something reminiscent of a certain orange person in our lives, and that was on purpose, clearly. But we didn’t want that to be overly reminiscent. The parallels are there and we just wanted to ride that story out as long as we could. He does end up in jail, by the way.

Just throwing that out there.

He ends up orange in a different way.

The Morning Show is interesting though, because unlike Fargo, it very directly and intently speaks to what is going on in the world. Quite literally at times, it’s replaying recent events. When you’re stepping into that kind of space, do you feel aware of the kind of archetype that you’re approaching?

In some ways. You could make the case: Is it Jeff Bezos buying the Washington Post? Is it Elon Musk buying Twitter? What is the exact analogy that you’re going for? It’s a hindrance to make it one thing. As you said, it’s archetypal. It really is talking about the influence of tremendous wealth in the space of creating facts or news or highlighting what is important. That’s a real existential question to our society. If the news is going to be controlled by three people, well, then where are we? Is that really a free press, or are we going backwards almost to the days of when the robber barons controlled everything? I don’t have an answer to it. I just think the show is doing its job and asking the question, and putting it out there and saying, “This feels kind of funny, right? This feels like there shouldn’t be this much money in the world, right?”

Is that kind of resonance important to you when you’re considering what kind of project to take on?

What I tend to really lean into is, yeah, is it saying anything? Is it saying something intelligent or thought-provoking or creative, or something that I would find interesting if I was a viewer? A lot of times, shows take a big swing about something and it’s like, “Well, who cares?” The network version of that was, “Let’s have these big, big ideas, these big high concept ideas because Lost worked—there’s going to be a thing where time stops or there’s a huge kind of thematic, story-oriented thing.” And people were kind of like, “Okay, but if it doesn’t say anything, then it doesn’t really matter. If it’s just a gimmick, then who cares?” That’s really the tricky part. You know, you go, “Why has SVU been on for 25 years?” It’s because people like the characters and they like what they’re doing. It doesn’t necessarily need to cure cancer, solve world peace or anything. It’s entertainment, and that’s worthwhile too. There’s a reason that Mariska [Hargitay] is still doing it. There’s a reason that [Christopher] Meloni went back. They like telling that story. Dick Wolf gets it. His shows are tremendously successful because they’re satisfying.

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As someone who has been working in TV as long as you have, and with Mad Men being a show that in many ways represented the greatness of where the medium was going, what do you think about where TV is right now?

If it’s not over a tipping point, it’s at a tipping point. I’m not the first to say this. I think we’re in the downside of peak TV. The Golden Age has passed—however you want to say it—which was inevitable. I mean, the rapid expansion of the streaming platforms and the significant, almost exponential desire for content made this inevitable. You can’t create as much content as the systems now demand and create it at a level where everything’s going to be great. What I think is disconcerting is the top-down request that I’ve only heard of—I’ve never had to deal with it as a producer or as an actor or anything—of what they call second screen, or passive watching content. Where it’s just, “We would like something that’s not super compelling so people can watch it and not pay attention.” Which seems to be at cross purposes: “We want it to be compelling enough so people won’t turn it off, but not so compelling that they’ll want to stop making dinner and sit down and watch it.” That’s not how I consume TV. I understand having something on while you’re doing something else. But I also tremendously appreciate the ritual of sitting down and watching TV. For us, Sunday nights, it’s New Jersey Housewives and it’s House of the Dragon.

And there’s no second screen going on for New Jersey Housewives.

No. [Laughs] We have made dinner, we are sitting down, we’re ready to go. So, I think that part of it is weird. I don’t know how that sustains itself. I don’t know how you can build a brand or a channel or platform or network on content that is underwhelming.

Certainly with your two shows that you’re nominated for, I could not imagine even attempting to watch them in that way.

Well, and also, how do you sell that to the people making it on both sides of the camera? It’s like, “Don’t try too hard. Just be okay.” What? It almost seems like it’s a solution searching for a problem. I don’t think that’s really a thing that people are demanding. What people are demanding is what they’ve always demanded, which is great shows. Because when one comes up, whether it’s a new season of an old show like Fargo this year or The Morning Show, people pay attention—and for different reasons. People like The Morning Show for different reasons than they like Fargo, and that’s great. Lorne Michaels used to always say that the currency of our business has never changed: It’s stars and hits. That’s what it always will be. We make new stars, we make new hits, but the audience determines that.

I know you experienced that with Mad Men—there was such a level of engagement and passion around that show.

We were very lucky on that show because it was one of those incredible serendipitous moments, and it doesn’t get talked about enough. We debuted right at the beginning of a couple of inflection points in the media and in culture. One of them was right before the iPhone, and one of them was right before recap culture and blogs. It was the burgeoning social-media moment. I still don’t have social media, but very few of us were tweeting about the show or Instagramming about the show or anything like that. We didn’t have to really engage in it—but the culture did. We got all of this essentially free media exposure that a show like us on a network like AMC at the time really couldn’t afford.

I remember when we first started that the ads that were running on our show were for a roll-on headache medicine called HeadOn and timeshares. And then by the second season, it was Heineken and Mercedes. You could very much tell that something was happening. And that was a big deal for us. We were early adopters of blog culture, recap culture, all of what essentially used to be called the water-cooler kind of discussion, but had moved online. Everybody could contribute and write their own thing and get into the comments and do all that stuff. I loved it. It was part of what I loved about anything: TV, theater, books, any media. As soon as I’m finished with it, I immediately want to discuss it with somebody because I’m like, “Did you think what I thought?” or “What did you think of the ending?”

You’ve talked about the audience projections made onto Don Draper, which were infamous at a certain point. As an actor who was coming back every season, getting to play really rich material, did you always enjoy that kind of feedback loop? Was there an element of learning to tune it out?

No, I loved every part of it. To get to stay with any show for that long, which was the better part of a decade of my life—basically my 30s into my 40s—is a tremendous experience and an honor. I’ve spoken to other people who have done it at that level, whether it’s Bryan Cranston or the late Jimmy Gandolfini, who was a friend of mine, or Hugh Laurie. I would run into these guys at various functions and events, and we’d all commiserate. But it was always with a real sense of gratitude: “This is the lottery ticket.” I don’t mean that from a financial standpoint, although it is that too. It’s the career-defining thing, and you will get to do what you want to do—maybe not at that level ever again—and you really will get what we’re all kind of looking for, which is understanding and respect and appreciation. It’s the ultimate pat on the back, and a real feather in your cap and all the other analogies I can make. I look back on it with nothing but gratitude and a tremendous sense of awe that it even happened at all.

Can you talk about your bond with Gandolfini a bit? The Sopranos ended right as Mad Men began.

There’s a photo somewhere in the ether of Jimmy and I at the last Sopranos award show, SAG Awards or Golden Globes or something—he came up to me with purpose, and he’s a big dude. It was later in the evening, and he grabbed me by the shoulder and he just said, “I just want you to know you’re going to be great in this, and you’re next. You’re the next one.” And I said, “Okay. Thank you. I love everything you do.” That was just the beginning of him recognizing, “Okay, I see what’s happening here, and I recognize it because I went through it.” He maintained that relationship with me over the course of the years.

Watching what he had done post-Sopranos too, him trying to shed that mantle—that took so much out of him to be that guy. Not only on set and on screen, but the impact it had socially trying to be in the world: “Hey, Tony, how you doing?” Understandably, because it was a very popular show. But it’s debilitating at a certain point. It was interesting to watch him navigate that, and I think unfortunately his health didn’t allow him to have much more of that. I’m pretty good friends with his son, Michael, and we talk about a lot of that stuff all the time, just trying to find a balance in work and life and pick the things that you want to do and for the right reasons. He’s starting off on his career and he’s having a very good one so far. It’s been really nice to maintain that friendship through Mikey.

You mentioned you do not have social media, which rather abruptly brought me to a Girls5eva running gag. I’m not sure if you’re familiar with what I’m talking about.

I do, yes. [Laughs] That was run by me, by the way.

I was going to ask! So the gag is that you are always the first to post a selfie with a sad, clever caption when a famous person dies, so you can lead the roundups of celebrity reactions.

That’s a Robert Carlock-Meredith Scardino special. They came and they thought, “What dummy can we get?” [Laughs] I’m basically the Lenny and the Squiggy of those guys. Whenever they create a show, they’re like, “What idiot is going to say yes to this?” And I walk in the door and go, “Hello!” So yeah, Robert had asked me, “Hey, they want to do this. Would that be cool?” And I said, “Absolutely.” It’s really funny. I love that show, by the way. I wish that show got more buzz and love.

We agree with you.

Tonally, it reminded me a lot of Kimmy Schmidt, because the setup is kind of wacky and out there, and then the way it’s delivered is in this tremendously grounded way. Paula Pell is a national treasure, and I’m very glad that people are seeing her on a wider stage. Meredith Scardino wrote on Kimmy as well, so it was great to see those alums getting their due. Paula Pell wrote one of my favorite SNL sketches that I got to do, which was basically a one-note joke about a politician running for office named Pat Finger. He was running for congressman or something in Butts County. So the whole thing was, “Please, please, let’s put a Finger in Butts.”

You started working in that world with SNL and 30 Rock right as Mad Men took off. Playing opposite people like TIna Fey, was it ever scary to you, needing to rise to that level of funny?

Yeah. It’s scary. Getting out of your comfort zone, which at that point for me was Don Draper, was very scary. Doing SNL was very scary. You go into that building on the 17th floor, which is where all the writing happens, and then you go down to the stage on eight, and every surface is covered with legendary performers and posters—pictures of Belushi and Radner and Chevy Chase and Bill Murray and Eddie Murphy. Everybody. You just go, “My God, I grew up with this show."” The show started in ’75. I was four. It’s turning 50 this year. It’s overwhelming, but it’s tremendously exciting.

The best piece of advice I ever got was from Jason Bateman, who had hosted, and he said, “Just be their guest. You’re their guest. They want you there. Just take your shoes off and be polite and don’t tell them what to do. They know what they’re doing. They’ve been doing it in a while.” That’s what I did, and I had the best time. It’s just like riding a roller coaster. It’s over before you know it. You look up and you’re like, “Oh my God, it’s good nights already?” And then it’s in the books. It was a tremendous honor to be a part of that. And yeah, very intimidating. But the people I’ve worked with have never been shitty or tried to be, you know, “I’ll take this guy down a peg.” Everybody’s been very, “Let’s work together to make this turkey trot.”

This interview has been edited and condensed.