In the sexy new ABC drama series The Company You Keep, con man Charlie Nicoletti (Milo Ventimiglia) and undercover CIA officer Emma Hill (Catherine Haena Kim) cross paths at a turning point in their lives. After a chance meeting at a bar unknowingly intertwines their professions, their undeniable attraction keeps drawing them together in a way that could lead to dangerous consequences for each of their families.

During this 1-on-1 interview with Collider, Ventimiglia, who’s also an executive producer on the series, talked about how this became his latest project after This is Us wrapped, bringing most of the crew over, the appeal of playing a good bad guy, putting this ensemble together, his favorite cons, exploring the Nicoletti family dynamic, what made Kim the perfect co-star, taking away the question of will-they-or-won’t-they, and whether he’d ever direct an episode.
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Collider: This show is a lot of fun. We get so many shows that are so dramatic and that make you weep while you’re watching them, and it’s nice to have something that’s just fun.

MILO VENTIMIGLIA: That was the goal. That was the want. Coming off of This is Us, and how emotionally draining at moments that it was, but also emotionally uplifting, Russ [Cundiff], my producing partner at Divide, and I were looking to be a part of something that was just fun and entertaining. We wanted to give people a moment to unplug and disconnect from life, and just have a good time with Charlie, the Nicolettis, Emma Hill, and everybody on the show.

Image via ABC

It seems like figuring out what to do after like a long-running successful project ends isn’t the easiest decision to make. In deciding what would be next, after This is Us, was there anything that you were specifically looking for? Did you have a list of definite things you wanted to do and things you didn’t want to do?

VENTIMIGLIA: I didn’t have a list of shows that I was going for. It was a little more like, “Hey, I’ve just done five years as America’s father. What’s something different I can do? What’s a little different flavor? What’s a horse of a different color that I can play, with something that’s gonna maybe give an audience an experience and some fun and have them feel something, but yet is a completely new character. And when this show came up on our development radar, we jumped on board because Jon Chu invited us to be a part of it. It just made sense, as a company. It also made sense, as an actor. Here was this wonderful opportunity to play a pretty heartfelt, good bad guy, who is still finding himself at 40 and constantly having to reprise different roles that he plays in his professional life as a con artist.

Did you know immediately that this was something you wanted to be a part of?

VENTIMIGLIA: This project came to us last spring, or sometime in the summer, before I had wrapped up This is Us. I was going into the summer, just before Season 5 on This is Us, and this fell into our development. It was this and a few other projects that we, as a company, were putting together, but I also knew, in the back of my mind, “Okay, well, I’m gonna be free, as an actor.” So, as we start setting up these different projects and pitching different projects, this one just checked all the boxes, and it was also a project that felt like it fit on ABC. Having a deal with Disney and having worked with Disney for several years, they were wanting me to stay with the company, as much as we could. So, moving from NBC to ABC was important to Disney. It just all worked out.

You’ve talked about how you brought the crew from This is Us with you to The Company You Keep. How did that even happen? You hear about one or two crew members maybe carrying over onto different projects, but I don’t know if I’ve ever heard about mostly the whole crew.

VENTIMIGLIA: I had to do it quietly, actually. I had to walk around, from department to department, and go to each department head and just gauge their interest. After you do something together for five or six years, as a group, people maybe wanted a break from each other, just do something else. But what I found was that everybody liked one another. Even some of us that asked a lot of questions during the production meetings, everybody still respected that person that asked all those questions, that maybe takes a little bit of extra time. We just all worked really well together and it became apparent that, if we had the success that we did on This is Us, why couldn’t we just repeat that and replicate that, telling a different story with a different group of actors and different producers. And we have, so far. The crew is the heart of the show. They’re busting their asses and they’re doing great work, and I’m grateful that they came aboard and came along.

It must be an awesome feeling for you to keep that many people employed.

VENTIMIGLIA: What’s funny is that (This is Us creator) Dan Fogelman tells me he can sleep at night knowing that the whole crew is working with me. He was like, “Great, okay, they’re all taken care of.” They’re people that he had looked out for, through several years now, and now he’s passing that on to me.

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You’ve described Charlie has a good bad guy. Because of that, do you try to push things a bit with him, to remind the audience that he isn’t entirely a good guy?

VENTIMIGLIA: I think there’s a lot of opportunity, in whatever character you play, to find some redeeming qualities. Not necessarily all of them, but you do what you can. What I like about Charlie is that he has complications because of his profession and because of his family, so he’s not squeaky clean, and that’s just more interesting than anything. We’ve definitely had uglier moments for Charlie that are probably a little more on the professional side. The one thing that I’ve heard from a lot of people who have seen the show is that they’re rooting for Charlie to pull off these cons and crimes, and that they want to see him succeed, which is encouraging. It’s nice to see someone who’s on other side of the law, but they’re doing it for a better reason than the dirty criminals.

There are certainly worse people than him and his family in the show.

VENTIMIGLIA: There are.

We get a very clear sense, from the beginning, that there could be some really fun, really interesting cons throughout the season. Do you have any particular favorites that you’ve gotten to do, so far? Are there any personas that you’ve had so much fun with, that you’re hoping you can maybe bring them back again?

VENTIMIGLIA: We’ve got a gun runner coming up, of unknown romance language descent. He was a lot of fun. The photo assistant was pretty charming and lovable. We bounced around quite a bit. Some of these cons and some of these characters function a little more in real life than anything. It’s just strapping on a different identity and trying to see through who the target is, who the mark is. I’m sure some of them will pop back up. What’s more fun is seeing the con collective material, like wigs or clothing or a ring or glasses. All of that gear is shared amongst the family. You may see Charlie in a pair of glasses over here in one con, and then you may see Leo or Birdie in them in the next.

With a family like this, who clearly has been doing this for a long time, I would imagine they have their routine and their things that work for them.

VENTIMIGLIA: Yeah, they definitely do. They’re picking up jobs from and farming jobs to other folks in the neighborhood, and they’re spreading the wealth. They’re not just taking for themselves. When the family makes money, other people make money.

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When you’re someone like Charlie, whose family has made a business out of lying and manipulation, is it challenging for him not to lose a sense of who he really is, since he can’t really be that person with anyone other than his family, or is he able to maintain who he is, underneath all of that?

VENTIMIGLIA: I think he’s able to maintain who he is underneath all of that, but I think he’s gotta be very selective about who he lets into his world. The truth is, if he slips to the wrong person and lets them know that he and his family are pulling these cons and grifts, maybe they have a moral compass beyond Charlie and the Nicolettis and they say, “Hey, I need to report this to the proper law enforcement channels.” So, I think Charlie sets himself up for a bit of a lonely life. He has a lot of strength within himself to understand that he’s gotta look out for his family.

One problem with living from score to score, as a family of con artists, is that you have no recourse. If someone cons you, there’s nothing you can do about it. How will the betrayal that happens in the pilot ripple through the season? Is that going to be something that this family is going to have to continue to deal with?

VENTIMIGLIA: Yeah. The con that Tina pulled over on Charlie is ultimately something that they’re gonna have to wear for quite a while. Being indebted to the Irish mob and Daphne is something that propels the season. They’re constantly watching as they’re pulling off cons to pay off that debt, thinking they’re getting a little more out of the hole, but finding themselves deeper and deeper in a bad situation.

Normally, viewers have to spend seasons of a show getting frustrated because they don’t know if the characters will ever get together. What is the fun in getting that out of the way and just getting to play with that dynamic, from the very beginning?

VENTIMIGLIA: The fun is probably just understanding how it’s actually gonna work between people that are so invested in their professional lives. How does that work, personally? That’s what we explore, going through the series. You may have two people that are right for another, but can they actually be together? Does it work, or is it something that’s just a moment in time, and you have to move on from it and accept that it just doesn’t go the way you think it will. Do those people remain in one another’s lives? What does that look like?

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It’s funny that when these two characters meet, they ask each other to reveal something true, and in that moment, Charlie tells Emma that he’s a criminal, and Emma tells Charlie that she’s CIA, but neither of them believes the other’s truth. What do you think it says about them that, even though they have that moment where they’re honest with each other, they don’t seem to believe each other?

VENTIMIGLIA: I don’t know what it says about either of them. I think they’re both wanting truth and honesty, but they’re also not willing to sacrifice or compromise with the holes they’ve dug themselves in, professionally. Being honest in a moment, after having wrapped that truth in a group of lies, how much can you rely on that truth then? It becomes a little flimsy. Even though it was all in good fun, there was a lot of mistrust built around even one single truth. That doesn’t trump everything.

Even without knowing that Emma is CIA, for Charlie to get involved with anyone who doesn’t know he’s a con man is a risk. What is it about her that makes him take that risk, when he clearly knows he shouldn’t be?

VENTIMIGLIA: I don’t know. That’s the one thing I can’t answer. That’s way too risky. In my mind and in my opinion, Charlie has been reckless, for himself and for his family, and I can’t answer that one for him. Sorry.

The success of a show like this obviously largely depends on the chemistry between the two leads. When that’s so important to what you’re doing, do you have a moment of panic, before casting your co-star? Were you ever worried that you wouldn’t find the right person?

VENTIMIGLIA: You put it out there, and you put your faith in process working. Sometimes it is a leap of faith and you’re hoping that someone will deliver, but there are also a lot of references. People forget that Hollywood is, in fact, a business, and people’s resumes are checked, double-checked, and triple checked. References are vetted. You start calling around and asking about people, to understand who you’re getting into business with. There’s the creative aspect of it, but there’s also just being around people and the kind of people you surround yourself with. I don’t think there’s ever a place of fear of not finding the right person, but it’s about finding the right person that’s gonna work for everyone. We know what we need in front of the camera and behind the camera. You have to find someone that’s gonna satisfy the director, casting, a studio, and the network. It’s all a math equation and a puzzle that’s put together in different dimensions, and that can feel nearly impossible or improbable to make happen.

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What was it like, the first time you met Catherine Haena Kim? Did you get an immediate sense that she was the right person to play this character?

VENTIMIGLIA: There was an excitement. There was capitalizing on what we all saw in her. I believe she hadn’t really gotten an opportunity like this, ever in her career, to play someone that felt like there was a lot of room to breathe and create for herself, and work with our writers, and work with our production teams, to have ownership stake in it, as well. We talked about how it was her desire to do the work and to be there. It came from a very pure place of, “Look, I’ve done X, Y and Z, over my career as an actor. I’ve also bartended and taken job jobs, just to keep the lights on.” She had a real want to collaborate and be present, and we all saw that. For that, we were like, “Hey, let’s give someone an opportunity.”

We’re also in a position where, as producers, we could give a relatively unknown actress an opportunity that wasn’t gonna hinge or hang completely on her. There’s myself, and Charlie, at the center, and we were able to build a cast with a lot of wonderful actors, on both sides of the families. Billy Fichtner, Sarah Wayne Callies, and Polly Draper are all very, very known. James Saito is very known. Tim Chiou has worked, but maybe isn’t as recognizable, even though you know his face. Same thing with Freda Foh Shen. Felisha Terrell, who plays our big bad Daphne, has worked and been around, but also said she hasn’t had an opportunity like this, ever, to explore a character the way that she can with Daphne. It’s wonderful to give opportunities. You’ve gotta give people a chance. Someone gave me a chance, a long time ago, and as a producer, I’m just looking to pay that forward.

Once you had all the actors in place, did you have time to get to know each other? What was it like to find the chemistry between not just Charlie and Emma, but with Charlie and his family?

VENTIMIGLIA: When you’re jumping into a new group of actors, who are all peddling emotions and we’re all emotional beings, and we’re also coming to it with our own ideas and intellect and wants, creatively, it doesn’t matter what the setting is. Whether you’re playing what Charlie and Emma are, or it’s Charlie and Birdie, it’s all communication and having conversations to understand how you can support your scene partners, and what you can give them and what they can give you. It’s just collectively finding what’s best for the show. It’s all the same. It’s just making sure you’re on the same page. If someone isn’t feeling good about something, you communicate why. If you’re both feeling great about it, then you’ve found a moment that’s pretty wonderful. These characters were allowed to live, and it’s pretty wonderful. It always goes back to communication. If you over talk what you play, you can make sure that you have this roadmap to accomplishing what you’re wanting to accomplish, within the context of the scene or an episode of TV. because you are to hop in the car and head to the airport.

You directed some episodes of This is Us. Would you like to direct an episode of this show? Is that something you’ve thought about, or that you’re planning to do? Even if it’s not in the first season, are you hoping to direct an episode?

VENTIMIGLIA: The difficulty for me in directing this show is that I’m constantly needed on set, so I have no time to prep. The only opportunity I’d probably get to direct would be the beginning of a new season. I was on a Russell Crowe movie (Land of Bad) when we were prepping the first episode of this, I wasn’t able to do it. And we had Ben Younger direct the pilot, so I wasn’t able to direct that. It’s something that I, of course, wanna do and plan on doing. We’ve got some great directors lined up through the season, like John Huertas and Anna Mastro, and we’re trying to pull in some friends to come in and be a part of our group. We’ve already started planning and mapping out, should we get picked up for a second season, who’s gonna be involved and pick up some episodes. We’re trying to keep it all within the family. I’m really, really doing my best to keep it all within the family, as much as we can.

The Company You Keep airs on Sunday nights on ABC and is available to stream at Hulu.