In a short time in Hollywood, James Wolk has amassed a series of credits that most young actors would kill for. In addition to roles in series such as Lone Star, Shameless, Political Animals, and The Crazy Ones (Robin Williams’ final TV series), Wolk made quite a mark as the mysterious Bob Benson during the past two seasons of Mad Men. He’s also appeared in several independent films including Rita Merson’s first feature, Always Woodstock, which opens today in select cities (and is available on VOD).

always-woodstock-posterAspiring singer Catherine Brown (Allison Miller) finds herself living a life she never dreamed for herself. Stuck at a dead end job in New York at a large record label, Catherine spends her days as the wrangler for the label’s most difficult star (Brittany Snow).  But when she is unceremoniously fired, and then comes home to find her long-time fiancé (Jason Ritter) in the arms of another woman, she decides that it’s time for a change. Catherine moves back to her family home in Woodstock to get back to what she has always wanted to do: write music.  One night, at a local bar, Catherine stumbles into local doctor Noah (James Wolk) and cannot deny the chemistry between them. Little by little, Catherine starts to write music, helped by a local legend, singer-songwrite Lee Ann (Katey Sagal).  As Catherine and Noah start to fall in love, she realizes that success has a lot to do with finding your true self. Always Woodstock also stars Rumer Willis, Alexie Gilmore, and Ryan Guzman.

I spoke to James Wolk about this film and his crazy experience on Mad Men.

Danny Miller: Noah seems like one of the most “normal” roles you’ve had. Was playing the nice guy in a movie a relief after some of your other recent parts? 

James Wolk: You know, one of the best things about being an actor is that you get to take on all these different characters — it’s always exciting. My mom always wanted me to be a doctor, so that was fun! I did enjoy playing someone with clear motivations for a change.

You’ve worked with some very well known directors as well as several first-time directors. Does that lack of experience ever worry you? 

Rita Merson did a great job on this film and commanded a lot of respect on the set, both with her script and her directing. You never know when it’s someone’s first film. If you like the script and you get a good vibe, you just kind of roll the dice. This was a very fun project with an incredible cast — Allison is a wonderful actress. You have to trust your gut feelings. Look, some of the most experienced directors can have a movie that goes haywire, you just never know. You take everything into consideration and say, “Okay, I want to take a chance on this.”

I imagine making a small film like this is a very different experience from some of the more high-profile projects you’ve been on.

It kind of feels like everyone is thrown onto a boat with oars and we all have to row together to get to shore. There’s definitely an excitement that comes with that kind of timeline. The good news is that there’s no time to overthink things — you just kind of run into it.

alwayswoodstock2

It was a pleasure to hear Allison and Katey Sagal sing in this film. Were you hoping that Dr. Noah might get a chance to pull out his guitar?

No, I was quite happy to leave the singing and guitar playing to Allison and Katey — they do it so beautifully. But I actually love music and I do play the guitar a little bit — nothing professionally!

I know that you can’t say anything about the upcoming episodes of Mad Men, under penalty of death, but I have to say how intrigued I am by your character, Bob Benson. It’s so rare for a new character to come on the scene that late in a series and engage the viewers to the extent that Bob has. Is Mad Men a show you were desperate to get on?

Well, to be honest, I did always think it would be a great show to be on but I had no idea what the character would be like when I auditioned. All I knew is that they were reading people for a new character but they told us nothing. So I went in and read for Matthew Weiner and got the call that very day that I got the role — it was so quick! But even then I had no idea what was going to happen with Bob Benson, I just knew that he was some new guy at the firm. I ended up having an incredibly wonderful and creative journey with that character.

Is it strange working under such a shroud of secrecy?

Yes! I think the weirdest thing was that I was working on the show for about six months and I couldn’t even tell my friends and family what I was doing. I couldn’t say I was on Mad Men at all because they like to keep new characters a total surprise. I was putting in all this hard work and I literally couldn’t utter a word to anyone I knew that I was on the show. That was difficult!

madmen1

Did being on Mad Men change how people respond to you on the street?

Yeah, it’s been gradual for me. The best story about that happened when I was in this very remote part of Kauai. I was hiking with my girlfriend with almost no one around and there was this couple a ways away. Suddenly I hear the woman screaming over at me, “Hey! Are you Bill Benson?” She got the name wrong but I still couldn’t believe it because we weren’t that close to them and I had a beard at the time! I just laughed and thought, “Well, this has certainly reached the masses if I have a beard and I’m on the far corner of an island and people are calling out my character’s name!”

You’ve had the chance to work with so many great people during your career. How was it working on Robin Williams’ last show?

So amazing, I loved every minute of it. It was really special. I also played Sigourney Weaver’s son on a mini-series called Political Animals with Ellen Burstyn and a killer cast. I think my M.O. is that I do really good shows with great people that only last one season. But it’s all good!

Any other movies coming out?

I’m really proud of the two films I did this summer. One of them is a comedy called This Is Happening by Ryan Jaffe, another first-time director. Mickey Sumner plays my sister and Cloris Leachman is my grandmother. I had a blast on that. And I also made a film called The Stanford Prison Experiment with Ezra Miller and Billy Crudup that’s a psychological thriller based on a true story. That was an awesome experience as well.

Well, good luck on the upcoming craziness with the final episodes of Mad Men, even though I know you can’t even tell me to what extent Bob Benson will be around.

You got that right. But thanks!