How Milo Ventimiglia identifies with con man Charlie in ABC's sexy 'The Company You Keep'

Spoiler alert: This story contains details from the premiere of “The Company You Keep.”

From The Big Three to the big con.

Milo Ventimiglia returned to TV Sunday as a swindler, after a brief break following the conclusion of NBC's “This Is Us” in May after six-season run. Sans Jack Pearson's mustache, he leads ABC's “The Company You Keep” (10 EST/PST), created by Julia Cohen and Phil Klemmer and adapted from a Korean drama.

Ventimiglia, 45, portrays Charlie Nicoletti, a man devoted to his family business of conning. But the premiere episode reveals the suave Charlie is the one being hustled. His fiancée, who robs the Nicolettis of $10 million from a high-stakes heist, putting his family, which owns a Baltimore bar, in debt to a major criminal organization.  

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The role of Charlie appealed to Ventimiglia, who appreciated how different the character was compared to Jack, an adoring father of three and doting husband.

“He's got a lot of layers,” Ventimiglia says of Charlie. With "the complexities of these cons the family pulls off, he's got to be a chameleon, and he's got to be charming, and he's got to be engaging. He's also got to be dangerous.” 

In addition to "This Is Us," Ventimiglia also acted in hit shows shows "Heroes," on NBC, and WB's "Gilmore Girls."

When contemplating a role, he looks for the opportunity to have fun. “You've got to know that it has legs," he says. "So when ... I was looking at this as an actor, it was, ‘Hey, is this a character that is going to be challenging and satisfying? Is it someone that is going to go the distance? Do we have enough story within who all of these characters in the show are?’ And I think we do.” 

Charlie nurses his heartbreak at a hotel bar, where he meets Emma Hill (Catherine Haena Kim), a CIA agent who has discovered earlier that day her boyfriend was having an affair. While knocking back drinks, the two playfully lie to each other about their jobs and upbringings.  

“OK, now tell me something true,” Emma demands.

"I’m a criminal,” Charlie says, in a brief moment of honesty, to which Emma responds, “I’m CIA.” They both laugh off the truth and end up spending 36 hours in a hotel suite getting to know each other and having passionate sex.

“What we're looking at in the beginning, (is) two trains on a collision course,” says Ventimiglia. “How do lives and heart and emotions unravel beyond that?” 

Charlie is torn between pursuing his new love interest and focusing on his family’s hustles.

“Charlie's going through a bit of a transition where he's existing in a way that he has for so long with his family,” says Ventimiglia. “They've been pulling grifts and whatnot since he and (Charlie’s sister) Birdie (Sarah Wayne Callies) were kids. It's all very second nature to him. So identifying that maybe you want something different and you want something more and the inspiration behind that is a new romantic partner, I can definitely identify with that.” 

Ventimiglia and Kim’s chemistry is off the charts. While the scenes appear steamy onscreen, Kim describes them as funny, silly and a tinge awkward to shoot.

“It's like we're in this bathtub and being all sexy and in between, I'm like, ‘If I see one extra bubble, I'm going to kill you,’” she says laughing. Or in a scene where the couple is having sex in bed, “There's our wonderful hair and makeup team and wardrobe team and they come in and somebody will offer me water and powder my nose and brush out my hair. I'm just like, ‘This should be a service you get in real life.’”

Though Charlie and Emma have an intense connection, their jobs naturally put them at odds.

“Emma has been chasing the woman that's holding Charlie's family’s debts in hand,” says Kim, 38. Despite “a fun fling for the weekend,” which “turns into something more substantial, they have no idea, of course, that things are going to get complicated professionally for both of them.” 

But Ventimiglia says it won’t be too long before the characters discover who their love interest really is. He promises, “It happens pretty quick.”

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