In just four years, since his breakout roles in 2010's You Again and the critically-acclaimed but short-lived drama series Lone Star, James Wolk has put together an impressive string of performances. While he's best known, of late, for playing Bob Benson on AMC's Mad Men, he has also showed off his diverse talents in For a Good Time, Call..., Shameless, Happy Endings, Political Animals and The Crazy Ones. The actor returns to the big screen this weekend in the charming indie Always Woodstock, opening in select theaters and on VOD formats November 14.

The story centers on the quirky Catherine Brown, stuck in a miserable job at a New York record label, who decides she needs a change of pace. She packs up everything and moves to her family home in Woodstock, New York. It's there she meets charming local doctor Noah Bernstein (James Wolk)

I recently had the chance to speak with James Wolk over the phone about....

Can you talk a bit about your first reaction to the script and the character Noah Bernstein?

James Wolk: Yeah, it was sent to me and I thought it was a really, really nice story. I thought that the romance between Catherine and Noah was really interesting and I liked that both characters had a sort of shared history of lost parents. I haven't myself, thankfully, but I found that interesting, and I knew some of the people involved in the film, and I was really looking forward to getting involved.

Did you actually shoot this at Woodstock?

James Wolk: No, this was not shot at Woodstock. This was actually shot in California. This was shot up in a ranch, during a time of year where it looked like Woodstock. It was very northern, upstate New York. Yeah, it's amazing what they can do.

I would not have guess California at all. It did not look like most films that are shot here.

James Wolk: Right, yeah. It's unbelievable. In fact, some of the scenes that were supposed be really nice, New York, cool evenings, were actually freezing, because we were in the canyons, up north of Los Angeles, and it was like 30 degrees. It was freezing.

For something like this, did you have a lot of time to shoot this?

James Wolk: No, there wasn't a ton of time. When you're doing an indie, you're limited because the budget is smaller than what it would be otherwise. With this, we had time, but not a ton of time (Laughs). Indie's are really fun in that way, though, because there's a raw feel. Everyone is prepping and doing what they need to do, and then you just go. There's not a lot of time... time is at a premium. There's a yin and yang to it. The good part is that, there isn't time to over-think things. The bad part is you always, as an actor, you always want to keep trying, keep playing. Suddenly you'll find a choice in one of the last takes that you wish you could keep playing with that choice. It's both good and bad, but, ultimately, you just have to adapt to the environment. Instead of knowing you're going to have 10 takes, you really have to grab the other actor and do a rehearsal prior to the camera turning on, so that when it does turn on, you're already kind of warmed up.

I imagine it had to have been so much fun shooting with Allison (Miller). Her performance is so hilariously quirky. Was it hard trying to keep a straight face when she's doing all of this crazy stuff on camera?

James Wolk: Yeah, she's fantastic. Working with Allison was amazing. She's such a nice, kind-hearted, fantastic actress, and really funny. It really brought a lot of levity to the set, and we really had a good time together, yeah, absolutely.

This is (director) Rita (Merson)'s first film. It had a really distinct feel to it. Is there anything that struck you about how she works during your time on the set?

James Wolk: Yeah, I respect Rita for having a really strong vision of the way she wanted her film to be made. I think her confidence level, thankfully, was really high. Sometimes, with first-time directors, they may be a little gun-shy and they may not be able to take control of the set. I really respect Rita for having a strong vision for how she wanted this film to go. She's the writer-director, so that's a really positive thing that she can come and take control of the set.

Is there any behind-the-scenes memory that will always come to mind when you think back about this project?

James Wolk: I remember there was a scene outside where Allison and I were walking with the bike, and it was probably 25 degrees out, and we had to pretend like it's a cool 50-degree night, wearing spring jackets or something. I just remember us both shaking and when the camera turned on, we were trying to convince our bodies not to shake as we were talking. That's something I'll always remember, for sure.

It looked like a fairly pleasant night on screen.

James Wolk: I'm glad it came across that way.

Is there anything that you're working on now that you can talk about?

James Wolk: Right now, I finished two other indies this summer, which were really great experiences. One of them is... the name just changed... it's called This Is Happening, by another first-time director, who is an experienced writer. We had a great time shooting that, and it's getting into the festivals right now. I did another film called The Stanford Prison Experiment, you may be familiar with that story.

I am, yes.

James Wolk: It's a really interesting, true experiment that happened up at Stanford. They made it this summer, and I really felt fortunate to be a part of it, with this really supremely-talented cast. It was a great experience. Both of those are in post right now.

I'm a huge fan of the German film Das Experiment, which is loosely based on the Stanford Prison Experiment. It was phenomenal and the whole story is so compelling.

James Wolk: You know what, I didn't see it, but I heard great things about it, and I am familiar with the fact that it exists. I heard really interesting things about that. I would try to compare the two, but I really have no idea what that film is (Laughs), other than the title. I think this should be pretty cool.

Are they aiming for next year on that then?

James Wolk: You know, I don't want to say, because I don't want to mis-speak, what the directors have envisioned for it. We wrapped this summer, and it's certainly festival-bound. With any independent film, that's part of the story. I know that those guys are really talented, the group working on that, but outside of that, I don't know the timing or any of that, but I'm excited to see what happens with it.

Is there any chance that Bob Benson will come back in the final episodes of Mad Men?

James Wolk: Oh my gosh, that is the question that I wish I could answer, but I can't.

I'm such a huge fan of the show, and I'm just chomping at the bit for them to come back.

James Wolk: Yeah, absolutely. That's one heck of a show. They've got some geniuses working on that thing, some really, really creative people working behind the scenes on that.

Having starred in a number of different TV shows and films, is there a medium you prefer?

James Wolk: You know, I'm drawn to the character and the script first, and whether it's a movie or TV is becoming less and less significant to me. I mean, listen, I think making the perfect film is like the Holy Grail, but I do believe that outside of that perfect film, I think people are looking at film and television as equal mediums. Last year, Matthew McConaughey's Dallas Buyers Club was unbelievable, and you look at his work on that, and his work on True Detective, I don't know which performance I prefer. I think they're both wonderful performances. For an actor, I think it's a really good time to be working in either medium.

Absolutely. There was such a stigma attached to TV actors, less than 20 years ago. If you were a TV actor, you never starred in movies, and now that's gone.

James Wolk: I've only been in the business seven years, and I think it was maybe even 10 years ago that stigma still existed. It's amazing, isn't it? I'm sure, from your perspective too, it's really interesting to see. I think it's great that those barriers are being broken down, because there's so much great storytelling being told in television.

Just to wrap up, is there anything you'd like to say to anyone who may be curious about Always Woodstock about why they should give it a chance in theaters or on VOD?

James Wolk: Yeah, if they're looking for a really sweet film with a great romantic story, and great music interwoven into the fabric of the film, then yeah, definitely check it out.

Excellent. That's about all I have. Thanks so much, James. It was a real pleasure.

James Wolk: OK, take care. Thanks.

James Wolk's Always Woodstock arrives on VOD platforms and in limited theaters November 14.