Over the past five seasons on Mad Men, Rich Sommer has come to be virtually identified with his character, the socially awkward but basically likable media head Harry Crane. At this point, it’s strange to see him in other shows and movies outside of the offices of Sterling Cooper Draper Pryce. But we’d better get used to it. Sommer is in two movies at Tribeca: The Giant Mechanical Man, a romantic comedy-drama in which he co-stars with Jenna Fischer and Chris Messina, and Fairhaven, a small-town drama in which he also co-stars with Messina — and he’s finally getting a chance to show his range. He recently sat down with us to talk about his new movies, what he’d do with Harry Crane if he had the chance, and his notorious obsession with board games.

So, you and Chris Messina are in two movies in Tribeca together. Are you guys best friends now or something?
We actually did three movies last year, which is really weird. We’re also in Celeste and Jesse Forever. I did three independent movies last year, and he was in all of them. I did Mechanical Man because of Jenna [Fischer] and Lee [Kirk, who wrote and directed the movie], and then Chris was going off to do Fairhaven and said, “I’m going to do this other movie. One of the other guys dropped out, he’s unable to do it. Would you want to take a look at the script?” In Mechanical Man, our characters basically just have a handshake together, but I am such a fan of Chris’s work that even if the script had been terrible I would’ve done that second film.

All of these films have actors in key creative roles. Fairhaven was written and directed by actors, Celeste and Jesse was co-written by actors, and for Giant Mechanical Man, Jenna Fischer was involved very early on in the writing and development process. How is that different? Is it different?
It is definitely different, to some extent. Obviously, people would like these movies to sell and gain distribution and in turn make their money back and maybe turn a profit, but with creative people at the helm, it becomes more about the subject and substance of the film. That’s certainly true for all three of these films, but especially in Mechanical Man, in the way it’s brought together. It was a very collaborative environment. Jenna wasn’t the director, but she was involved very deeply from the very beginning. And Lee, who wrote and directed, has acted before. It was run all by people who were contributing throughout. It wasn’t about money. It was about heart and ideas and excitement, and that’s the key difference.

Your character in Fairhaven is wrestling with fatherhood, which I imagine you can relate to as well, being the father of young children.
Yeah, Messina and I improvised part of a conversation in the film about fatherhood. He asked, “How do you like being a dad?” I said, “I hate parts of being a dad, and I love parts of it.” It is a complicated thing that we do as fathers. There’s nothing better, but it’s also like you signed a lease with the worst roommate in the universe, who screams and throws things at you, and you can’t throw them out of the apartment. And they’re also super-litigious, so you can’t even talk back! A child is like a litigious, rageaholic roommate that you can’t kick out. And they’re on the payroll, too, for some reason!

Let’s talk about your character Harry Crane on Mad Men. Over these few seasons, I feel in some ways that he’s changed more than any of the other men on the show. He initially started off as comic relief, almost, but his arc feels more human now.
I love what they’ve done with Harry. But you know, if you look at an episode from early on in season one, and you look at an episode now, he certainly looks different — more than any other character on the show, maybe except Peggy — and carries himself differently, and speaks to Don and Roger differently than he did then. But I don’t necessarily feel like he’s that different as a person. I don’t think anything rings false with how they’re writing Harry now versus how they were writing him then. It’s because he’s on this TV train at the company, so he swings it around a little bit more. I think he would have swung it around a bit more back then, too, but he would have gotten fired. He just has a more important position now and has a little more leeway with what he can do.

So, if it were up to you, what would you have happen to Harry?
As an actor, I would like him to stay put and not go anywhere. [Laughs.] And I would like for him in the final episode of the final season to say, “Well, guys, I’m moving on to bigger and better things, bye!” But as a character, even though he’s socially dumb, and he makes mistakes and sticks his foot in his mouth, I would love for him to remain the lovable douchebag that he is. I hope he remains that way, but also keeps lucking into these things. I think eventually he’s going to run his own joint, for sure, whether it’s an ad agency, or a talent agency, or a power agency. I also would love for him to get a divorce — Jennifer is really bad for him. But who knows? I have no power over what happens to Harry. Whatever the opposite of power is, that’s what I have when it comes to that character and that show.

You’re also a huge board-game aficionado, and you maintain a blog where you write about and review games. How did you get started on games, and which one is your favorite?I got started when I was living in Cleveland. There was a board game store that was going out of business, and they were on deep, deep, deep discount. I had no money, and I wrote down the names of all these games and I went online to this site called boardgamegeek.com to research them, and I immediately got obsessed. I found the ones I wanted to buy; I went to the store and bought a couple of them. And I went from having those two games to now owning something like 375. My favorite is one that I’m sure you’ve never heard of. It’s called Die Macher, and it was designed by Karl-einz Schmiel in 1986, and it’s about the German political system. It takes five people to play, and each person represents a different political party, and you have a series of seven elections, and each election has, like, different parts. It’s intimidating, but it’s a beautiful game, and it’s intuitive, and it makes sense. It’s a lovely thing.

Which is your least favorite?
The Ungame. Which I had to play when I was seeing a shrink in fifth grade. It’s a game where you roll a dice and then it’s, like, “So, how do you feel about your mom?” It’s not a game. That’s why it’s called the Ungame. They pretend it’s a game just by putting it in a game box. It’s awful.