From his stint on Happy Endings making the heart of Adam Pally’s Max skip a beat, or the caring brother to Sebastian Stan’s gay addict T.J. on the gone-too-quick Political Animals, to this past season when he touched the unsuspecting knee of Vincent Kartheiser’s Pete Campbell on Mad Men, James Wolk has not only made us swoon with his dreaminess but also surprised us with his array of characters in both sitcoms and dramas.

This fall, we’ll see Wolk back in the sitcom world as Zach Cropper who, in the actor’s words, is “the office lothario” on the new CBS sitcom, The Crazy Ones. Created by David E. Kelley (Ally McBeal, Boston Legal), the series revolves around a Chicago-based advertising firm run by the father/daughter team of Simon Roberts (Robin Williams) and Sydney Roberts (Sarah Michelle Gellar).

James Wolk as Zach Cropper in The Crazy Ones. (photo: Monty Brinton/CBS)

We caught up with Wolk earlier this week at the CBS TCA party in Beverly Hills and he explained his journey in TV the last few years, his hopes for his new character, and if he knew his character Bob's whole story when he started his Mad Men gig earlier this year.

TheBacklot: The first time we ever talked was at the Paley Center event for Lone Star.

James Wolk: I remember that! Like this day three years ago!

TBL: And look what’s happened in three years!

JW: It’s been amazing!

TBL: Have you been able to step back and take in everything these past years?

JW: You know what? It’s been really busy, and this summer I was able to take some off and just sit back and think about everything and it’s been an incredible time this last year.

Wolk, David E. Kelley, Sarah Michelle Gellar, Robin Williams, Jason Winer

and Amanda Settle at this week's TCA panel. (photo: Sonya Flemming/CBS)

TBL: Looking at your career and going from Lone Star to your stint on Happy Endings to Mad Men and now The Crazy Ones, can you make sense of the trajectory or is it just how things fell?

JW: You know, it’s about finding good material and being surrounded by amazing people, it truly is. I just feel so blessed for everything that’s come my way.

TBL: The pilot for The Crazy Ones was so fun. Talk to me about your character and where we’re going to see him go.

JW: He has Peter Pan syndrome. Zach doesn’t want to grow up. He’s the office lothario, he loves going on these wild adventures with Simon and B.S.-ing his way through meetings. I think there’s going to be a lot of fun to be seen there with Zack. He’s really going to enjoy the ride.

TBL: Talk to me about working with Robin Williams.

JW: Unbelievable. Incredible. He’s an icon and I love him as an actor. I love him as a human being. He’s everything I could’ve imagined and more.

TBL: And you held your own with him in the pilot when you guys do your riffing [with Kelly Clarkson!].

JW: Thank you!

TBL: Was that rehearsed or did you just go in and wing it?

JW: We did not rehearse that. We actually went in with the scene as written. We sat down, we started laughing and singing and before you know it we were 90 yards off the rails, cracking off [and] trying not to cry in the middle of the scene.

TBL: Talk about working with Sarah. Could we get some romance between Sidney and Zack down the line? What do you think?

JW: Who’s to say? I think anything can happen. It’s all up in the air. Sarah is amazing. She’s so great on the show and the relationship between she and Robin Williams – the Sydney and Simon relationship – I think is really the heart of the show and she’s lovely but who knows. We’re sitting at the beginning and it will be interesting to see where it all goes.

TBL: Was it important that the show have heart, which this one seems to have outside of being really funny?

JW: Those are the kinds of comedies that I love watching is that you can come back to something real, there’s a baseline that is real so for me that is important and it’s a David E. Kelley show so it’s going to have heart.

Wolk earlier this year on Mad Men with Vincent Kartheiser

TBL: What did you learn from your Mad Men experience?

JW: That experience for me was, one, of working with amazing actors and, in my opinion, one of the most incredible ensembles on TV. So just to watch those guys work and see a show that’s in its sixth season that’s still kicking ass and taking names is just fun to watch all that happens

TBL: Did you know when you stepped into the role where they were going with Bob?

JW: No, I had no idea on day one where that was going. Eventually it was revealed to me in order for me to play the character in a realistic way but day one I did not know that’s where they were going!

The Crazy Ones premieres September 26^th on CBS.