Mad Men’s James Wolk on the Bob Benson Reveal and His Favorite Fan Theory

James Wolk as Bob Benson. Photo: Jaimie Trueblood/AMC

Not since the dawn of Don Draper himself has a character on Mad Men been as mysterious as Bob Benson. The many theories ranged from plausible to Oh, come on. Bob’s a government spy! Bob is someone’s secret son! Bob’s a psychopathic murderer! Turns out Bob is — from what we know — another guy like Don, inventing his way to the top. And at the moment, he’s safe. In the last episode, Pete learned that Bob had been created out of a willingness to go fetch and a devotion to self-help records. (They really work!) But rather than expose him, Pete decided to keep Bob close because, like Don before him, Bob had proven cunning enough to fool the entire firm. James Wolk has no idea what’s next for his character beyond Sunday’s finale but says he feels very lucky to have inspired such rabid guesswork. Before Mad Men, he recurred in the since-canceled ABC comedy Happy Endings and starred in the short-lived Political Animals and even shorter-lived Lone Star. Now that he’s finally free to talk about Bob’s backstory, Vulture rang up Wolk to discuss how he came to know Bob’s big secret and what remains a mystery to him. He also talked about wanting to do for bar mitzvah emcees what Magic Mike did for strippers. (To which we say: Bring. It.)

You can finally talk about Bob Benson’s big secret: He doesn’t exist!
Yes! I can speak to Bob’s secret, although I feel like there are still some questions in the air. But, absolutely, it’s nice that some of the information is out there.

After the reveal aired, who did you hear from first?
I told no one anything, so I got a lot of e-mails and phone calls from friends and family. They weren’t about anything specifically, they were just generally like, “Holy shit.” “Oh my God.” It’s been amazing to see people go on this journey with Bob Benson. It’s been incredible to see.

When did you find out that Bob was an invention much like Don Draper?
What started to happen was I noticed there wasn’t continuity in everything he was saying. Once I started to sense that, Matt and I spoke and he let me in on it. You kind of learn things in installments here. You’re not told everything right away.

So you approached Matt with your suspicions then? The conflicting stories about his dad seemed to be the giveaway for most people.
Matt’s very communicative. He gives you the information you need to play it. So when we came to a juncture when I was like, Hey, something’s missing here, I think all parties were eager to sit down and talk. I was always curious to see where Bob was coming from, so I had information but not all the information. Things like the dad stories started to come into play. I think everyone caught that [laughs]. I knew something was going on by that point.

Did you have any ideas of your own in terms of what his backstory or agenda might be?
I was given enough information to play him, honestly. When I first read it, I was thinking, This guy’s a lot like Jimmy Stewart. That was my first reaction. Very Jimmy Stewart–esque.

Do you have a favorite Bob Benson theory?
My favorite theory is that Bob is Peggy’s son who time-traveled back from the future. I laughed forever when I heard that. Peggy’s time-traveling son.

What did they tell you in terms of how to play Bob in the very beginning?
What you see onscreen is very much a reflection of the script. When the words are so forthright and when you have someone so gregarious and eager to please, you can see that in the words. Every actor is different, but for me it felt like there was only one really honest way to play that, which is as a really kind, eager guy. It’s the only way those words could come out of my mouth!

Did you understand Bob’s admiration of Pete? I think it surprised a lot of viewers that out of all the people in the office, Bob seems to feel most strongly for Pete.
Sure. Yeah. I think the best way I can describe it is to say that Bob is very eager to help people. He cares for people a lot. We see him taking Joan to the hospital. He finds a nurse for Pete’s mother. And in that scene with Pete, we see him offering some sign of affection. How that’s interpreted by the audience and the exact motivation behind it, I can’t comment on.

So you’re saying it’s more than just pure professional ambition. He genuinely cares.
Uh, I can’t comment on that exactly, but it didn’t surprise me when that came across. We’ve been seeing a guy who is very comfortable with who he is. And again, that’s another situation where he sees Pete as someone who is hurting, who is in a tough place.

I think Pete’s a little scared of him now that he knows the truth. 
That was great, right? Especially for avid watchers who’ve been following since season one, to see that parallel with Don? It’s so interesting the way Pete learned from his past about how to handle the situation. It’s not exactly what Bob was expecting. Bob was ready to run.

Right. Up until then, nothing has fazed him. And everyone yells at him! Ken, Jim, Pete … did you ever feel like the resident punching bag?
It’s funny. There are so many pressures on these guys. You see them dealing with so much. And then Bob comes in smiling ear to ear. He’s an easy target, quite frankly. But he’s confident in himself. That’s something the producers told me: “You don’t become bashful about your own sense of self. He has real confidence.” Even though there’s an affable quality to him, there’s also a confidence, a steely resolve to take those punches and roll with them, which I loved.

You’ve said that your past as both a shoe salesman and a bar mitzvah emcee might have made you right to play this guy who can ingratiate himself with just about anyone. Tell me all about the emceeing.
I grew up in a town where there were an immense number of bar and bat mitzvahs. When I was 15, I was approached by one of the bar and bat mitzvah companies to, like, dance and pass out glow sticks and do inane stuff, and I was told that ultimately it would lead to emceeing. So I started when I was 15 and everyone thought I was 18 or 19 because I was really tall. No one knew my dad was dropping me off five blocks before the temple. I emceed in metro Detroit throughout college, and even when I moved to New York, I would actually fly back on a Friday, emcee on a Saturday, and fly back on Sunday so that I could audition during the week. It was a big part of my life.

And you enjoyed it?
It was fun. I look back on it very fondly and I’m grateful for everything it gave me, but I think I was ready to retire my emcee suit at the end of it. I did it for, like, six years! You can find old Jewish newspapers from Detroit that have my promotional ad in them. It was a totally insane time in my life. Paul Rudd was also a bar mitzvah emcee, you know? It was like being a local rock star in Detroit. I think it would be the funniest thing in the world to write a TV show or a movie about it. It’s prime real estate.

Hey, if Channing Tatum could do it … You also perform a little on your new CBS show, The Crazy OnesYou sing with Robin Williams in the first episode. 
That came out of nowhere. We were shooting the scene, improvising, and a writer threw out the idea to sing and before we knew it, we were improvising what I think will be known as “Drive-Thru Lovin’.” Luckily there was no intimidation factor. It was extremely impromptu. Pure fun.

You’re working for both Matt Weiner and David E. Kelley now. What are the differences in how they run their shows?
Both are obviously incredibly prolific. For Mad Men, we really had to stick to the script, and you want to. It’s not like you feel your hand is being forced. The words you get are the words you say. With The Crazy Ones, we were really encouraged to improv and go off script. It was interesting to be in both worlds at once because I was shooting them at the same time.

If Bob’s story continues into next season, are you able to return in the same way Alison Brie works on both Community and Mad Men? Have you worked that out with CBS?
We haven’t discussed anything formally, but if the opportunity exists and there is a further story to be told for Bob, I would love to be a part of it.

Mad Men’s James Wolk on the Bob Benson Reveal