You will probably instantly recognize Rich Sommer as Harry Crane from AMC’s Mad Men, undoubtedly one of the best shows on television, currently in the middle of its fourth season. Then you will probably ask yourself, “What else have I seen him in?” And it will start to bug you. Then his small, but memorable performances will start to creep into your brain, because they are memorable, and you will go: “Yes! Pam’s NYC friend on The Office! Anne Hathaway’s drinking buddy in The Devil Wears Prada! Burn Notice! Ugly Betty!” Then you will Google him and start following him on Twitter because he is hilarious, then you will watch his Funny or Die shorts because they are hilarious, and you will come to know him as Rich Sommer, not Harry Crane.

In late August Rich became the father to his second child right after being wrapped up in Emmy madness (as Mad Men is used to after winning Best Drama for the third year in a row), and still found time to respond to this interview, ie: GREAT GUY.

Serial Optimist: Hi Rich, how are you? Without getting into detail about your career, which we will touch on later, can you just tell us a little bit about yourself?

Rich Sommer: I’m okay, thanks. Tired, but okay. I am a newly minted dad of two. I’m married to a woman that is way too good for me. I am a little loud. I have obsessions, both long- and short-term. Current (most likely short-term) obsession: reading about and making fancy and/or old-timey cocktails. Former short-term obsessions: magic tricks, juggling, pool, AFI’s top 100 films. Long-term obsession example: designer board games.

I am a huge nerd.

SO: I’ve loved and enjoyed you on Mad Men, recognized you from The Office and The Devil Wears Prada, amongst other things, but what really piqued my interest in you was your “performance” for the benefit “The Night of 140 Tweets.” Can you tell us how you got involved with that? Did you know that now, if you type Rich Sommer in Google, the fifth suggestion is ‘Rich Sommer Underwear’?

Rich: I was invited to participate in the Night of 140 Tweets by one of its hosts, Paul Scheer. I brought a few of my actual tweets to choose from at the last minute, but Harris Wittels mentioned that he had thought about doing his naked. When he made clear he wasn’t going to end up doing it, I asked if I could use his idea. He let me. I doubt I would be on the back of the DVD case if I hadn’t used his idea, so I guess I owe him a beer or two.

SO: Would I be correct in saying your background is in comedy? I’m more referring to all of your improv work, and experience with the Upright Citizens Brigade in New York. When you first really started seeking to work as an actor, did you try to go more the comedy route? Drama route? Stage route? Or in the beginning, was it just “whatever I can book, I will book?” I guess I’m curious as to the mindset of an educated actor and trained improviser, what were your hopes and dreams after college?

Rich: Sort of, I guess. I mean, I did a lot of improv, yes. But I don’t know if that means my background is in comedy. At the same time I was improvising, I was doing as many straight plays as I could, and many of those were dramas. So it’s hard to say. I like comedy a lot, and I did a shit ton of improv class and performance for a while. But if I put my improv training up against the amount of straight acting training I have, the acting training wins.

That being said, I did seek out as much improv training as I could to supplement my curricular studies. I spent a couple of summers at the Brave New Workshop in Minneapolis, and I went straight into the Upright Citizens Brigade between my second and third years of grad school. I think I did all of that because it was the one aspect of my career I could somewhat control since the auditions and classwork were sort of prescribed for me.

My hopes and dreams were to make my living as an actor. In anything. Broadway, TV, Mentos commercials, whatever. So, yes, whatever I could book, I would take, at first.

SO: We were both born and raised in Stillwater. You, Minnesota, me, Oklahoma. I don’t really have a question for that, I just thought it was an interesting side note. What was your high school mascot and what kind of kid were you in Stillwater?

Rich: We were the Stillwater Ponies. Our football team won every game my senior year, and I went to every game. They were amazing. I mean, Aaron Runk? Our quarterback? Holy balls. So much fun to watch.

I was moderately involved in Stillwater, I guess. I was in a barbershop group with a bunch of dudes that were way older than me. I hosted the airing of our local parade on Public Access Channel 10 when I was twelve. I did a play that toured nursing homes. That kind of stuff.

Wait, that made me sound like a really good kid. I wasn’t entirely. I lied to a cop once. So there’s that.

SO: Do you ever improvise on the set of Mad Men? I imagine Matthew Weiner has a pretty tight script and read. Who do you think gets the funniest lines on the show?

Rich: No. Some physical stuff, sometimes, but almost everything is scripted. Not only is there no room for improv, but there’s also no need. Those writers are writing poetry. I can’t mess with that. They are way, way smarter than I am.

Oh, Roger Sterling, hands down, gets the funniest lines. They throw quite a few my way, and I am grateful, but he gets the lion’s share.

SO: What current shows, comedies, and dramas are you watching? Do you have any certain shows you just can’t miss?

Rich: I think the best show of the summer was Louie on FX. Just fantastic. Comedy-wise, I am so excited that It’s Always Sunny in Philadelphia is back. Looking forward to another season of Modern Family, and I’m hearing nothing but good things about this season of The Office. For drama, Breaking Bad is the only show I have to watch live every week. I can’t risk hearing about what happens without having seen it first. I’ve finally started on Dexter, but I’m only one season deep so far. Michael C. Hall is really good. And I can’t wait for Boardwalk Empire.

SO: Your Wikipedia page says you are a “keen board gamer.” I know what keen means. I know what board games are. I’ve just never heard the phrase: “keen board gamer.” Do tell.

Rich: It says that? I have had zero input on what’s on that page, so I’m as curious as you are. For me, “keen” connotes a certain aptitude at gaming. If so, it is a wholly inaccurate description. I lose almost every game I play. I love playing them, looking at them, reading the rules; but man, am I terrible at games.

SO: You have a new Funny or Die short that is about to come out. How does that come about? Are you just buddies with all the people involved with “The Big Dog” or is it something they just thought you would be good for? I’m always interested in how these things come together.

Rich: Many of the guys working at Funny or Die were doing UCB in New York when I was there. I consider several of them friends; so much of my involvement there comes from that. For “The Big Dog,” Charlie Sanders and I were on a Harold team together, and I think he and Eric Appel decided together to give me a call. I am always super excited to get a call from those guys, or Chad Carter, a friend/FoD writer/fellow board game nerd. They always have great ideas, and I love being one of the people they’re willing to work with. My most recent FoD video was called, “The Committee.” We made a couple of them. I think the second comes out in a week or two. Hope we get to do more of them. So much fun. Drew Pearce, the writer/director, knows how to make funny things look pretty.

SO: What would be the last line read in “The Book of Rich Sommer?”

Rich: The last line read? I’d hope it’d be the last line in the book; otherwise, you didn’t make it all the way through. And that would be sad.

SO: Well-played. Thanks so much, Rich, and big-time congrats on the current, amazing season of Mad Men, and most importantly to your newborn boy!

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SO Note: (Follow Rich on Twitter @richsommer, check him out on Funny or Die here, and not that I need to remind anyone but watch him on Mad Men each Sunday night on AMC at 10 PM |9 PM central)