David E. Kelley has dreamed up some unbelievable TV characters over the years, but the slick adman Zach Cropper played by James Wolk in Kelley’s new CBS sitcom The Crazy Ones, premiering Thursday, seemed like his most preposterous creation yet.

“Originally in the script, he was described as ‘George Clooney, but better looking and more charming,’” recalls Crazy Ones director and executive producer Jason Winer. “And on top of it, it’s a comedy, so you have to be funny. I thought that was impossible, but then in a later draft, David added the idea that he sings. And I was like, ‘David, you’re killing us! How in the world are we going to find somebody handsome, funny, charming, and who can sing?’”

Enter Wolk, who ended up being so perfect for the supremely confident protégé to agency head Simon Roberts (Robin Williams) that even Kelley couldn’t believe his good fortune. “James comes in and he hits the triple crown,” says the show’s creator and executive producer. “To be honest, we were all surprised at how easily he was able to riff with Robin. When I saw the first cut, we were all like, ‘Wow, we’ve got something even more than we anticipated.’”

Indeed, the biggest surprise to many who have seen the Crazy Ones pilot is that Wolk gets some of the biggest laughs. During a scene in which he and Williams improvise a racy jingle about fast food in an attempt to woo Kelly Clarkson as a McDonald’s spokeswoman, Wolk manages to one-up his comedy legend costar. “Oh, he can go more than toe-to-toe, he leads the way,” says Williams. “He kicked ass. Literally, I was going, ‘Damn! I’ve got to catch up!’ Which was wonderful, because it was very freeing to know that you’ve got backup. You’ve got a riff, and somebody is just right along there with you.”

Wolk, 28, has been surprising audiences ever since his breakthrough role in 2010’s Lone Star as Bob Allen, a Texas con man living a double life. While the Fox drama was critically acclaimed but infamously canceled after only two episodes, the actor persevered, earning more praise in last summer’s USA miniseries Political Animals before taking Mad Men by storm this season as another hustler named Bob: Bob Benson. “This is all pretty mind-blowing to me,” says Wolk of his Mad Men and Crazy Ones good fortune this year.

Though Wolk’s impressive comedy chops on The Crazy Ones will be surprising to fans who know him solely from his dramatic roles, the actor says he’s been honing them since he his childhood in Farmington Hills, Michigan. “We just had a free, fun-loving family, a ton of laughter, a ton of singing, a ton of goofing around,” says Wolk, who actively searched for a sitcom during pilot season last spring. “I’ve always loved doing comedy. I’m kind of a goofy guy at heart. So for me, this was really an amazing opportunity to be able to showcase that side of myself. And the people who know me best—my family, my loved ones—said, ‘Finally we’re really seeing the you that we know!’”

But it’s the part no one knew anything about—Mad Men’s enigmatic Bob Benson, introduced early in the season as an eager-to-please, always-grinning suck-up who eventually was exposed as a Don Draper–like chameleon who had invented his entire backstory—that really launched Wolk back into the ether. At first, thanks to creator Matthew Weiner’s über-clandestine approach to all things Mad Men, the actor knew as little about Bob as viewers did. “I really was in the dark when it first started,” says Wolk, who wasn’t even told how many episodes he would be appearing in. “I knew there was something beneath the surface, but I didn’t know exactly what it was. They email you your pages from week to week, so until you come to the table read you really don’t know exactly what the script looks like. So it keeps you on your toes. It’s also nerve-wracking! But ultimately, I had no idea where Bob Benson was going.”

He found out soon enough, however. A few episodes in, “I started to have suspicions that hey, this guy isn’t who he seems he is, and this is kind of a Talented Mr. Ripley–style guy,” Wolk recalls. “And then as it unfolded, and it became very clear that he was not who he said he was, Matt [Weiner] came down and had a conversation with me, and I became privy to what was going on.”

It was another chance for Wolk to play a con man character after Lone Star, though the actor can’t explain why TV creators keep seeing such a capacity for deception in him. “I don’t know!” he says. “I take it as a compliment because those are my favorite roles to play, quite frankly. I think it’s so amazing to play a role with duplicity, so I’m honored that I keep getting chosen to play these great roles.”

At the time of Lone Star’s abrupt cancellation three years ago, Wolk says he wasn’t sure he’d ever work again in Hollywood. “It was a weird thing,” he says now of coping with the show’s demise. “If you have a good head on your shoulders, you walk into this business and think, ‘Oh, I would never get swept up in the excitement of being in the limelight. That’s not important to me.’ And that very well may be, but when you’re on the ride that Lone Star was, which was this insane skyrocket to the moon, I would think even the most grounded people in the world would somehow start to believe in a little bit of that hype.

“And so when that goes away, it feels like you have failed somehow, because you’ve put a certain amount of stock and truth in that hype. But the lesson you learn is that that stuff can come and go with the winds, and what’s important is choosing work that has integrity and is fulfilling to you creatively. So there was just some interesting growth that went on with me because of that, and I really value having gone through that now that I’m standing here on the other side.”

After the show’s cancellation, Wolk bounced back with guest stints on Shameless and Happy Endings before his next high-profile role, as Sigourney Weaver’s son Douglas Hammond in Political Animals. Though the show, which was nominated for five Emmys, was billed as a miniseries, USA had intended to bring it back for a second season if ratings were robust. They weren’t, and Wolk still sounds wistful about what that second year could have been like as a slowly unraveling Douglas managed his mother’s (second) presidential campaign. “I was so happy that it was a miniseries, but had it gone … gosh, there was so much story to tell, and I love that Douglas was starting to come undone,” he says. “He was really coming unwound at the end of that. I loved that, and I was excited to see that go further.”

He feels the same way about Mad Men’s Bob Benson, he says, and is eager to return for the show’s final season, which AMC recently announced will be split into two parts. That’s assuming, of course, that Weiner wants him back. “I’d love to be back on that show. I had a great time working on it and I think they felt the same way. And if there’s a story to be told, I’d love to be there,” Wolk told The Daily Beast in July. Asked again in September if he had an update about Bob’s possible return, after the Mad Men writers room had reassembled and begun plotting out the seventh season, Wolk’s non-answer was telling: “Even if I did, I couldn’t say anything.” (Translation: see you soon, Bob!)

His Crazy Ones boss Kelley says he’ll try to free Wolk up if and when Weiner comes calling. “I’ve always been of the mind-set that you try to work it out,” Kelley says. “It’s good for the shows mutually and it’s good for the actor.”

That two big shows might soon be jockeying for his services makes Wolk even more thankful for Hollywood’s embrace after Lone Star’s flameout. “I’m so grateful have that support,” he says. “For people to keep saying, ‘We want to see more of this guy, even though the shows have not always been out-of-the-box successes,’ is a huge compliment to me. Maybe even more so than if it were just an easy path for people to jump on board. But to have them say, ‘Yeah, we know that that didn’t work out, but we want to see more of you,’ that’s been amazing.”