Milo Ventimiglia’s ‘The Company You Keep’ Kills Its Sexy Heist Vibes with Too Much Family Drama

Before “This Is Us,” Milo Ventimiglia’s major roles felt of one voice. There’s Jess Mariano, the troubled young rebel on “Gilmore Girls”; Peter Petrelli, a tortured nurse struggling to control his powers in “Heroes”; Robert Balboa, Rocky’s son (in “Rocky Balboa” and, later, “Creed II”) who’s stuck in his father’s shadow, even when he doesn’t know who he is without it. Ventimiglia’s specialty was playing the bewildered bad boy with a good heart, and whether it was a woman (like Rory), a calling (like Hiro’s), or a father (like Rocky), he just needed one thing to go right for the rest of his life to fall into place. In other words, he was the guy someone looked at and thought, “I can fix him” — and they were usually right. (Hell, Jess turned out great, and all he did was pine for Rory.)

Then “This Is Us” came along. Jack Pearson wasn’t some kid trying to put the pieces together; he was a super-dad; a dad enshrined in the minds of his children from the second he died in that tragic crockpot accident, all the way through his progeny’s steady maturation into parents themselves. Sure, Jack had flaws (alcoholism, a drunk father of his own, questionable facial hair), but they only endeared him to his family, just as they endeared him to tens of millions of viewers at home.

But even after Ventimiglia made the leap from adrift adolescent to assured adult, one uniting factor remained: earnestness. Jess may have been a shitty boyfriend in high school, but he was serious about Rory — he just didn’t always know how to express it. Peter also approached his responsibilities with purpose, and you know Rocky Balboa’s kid gave it his all. Jack did, too. Even when he wasn’t making life-altering speeches or sacrificing himself for the family dog/photo album, he made every moment momentous, from pool days to game nights. These were the times that mattered, the times worth remembering, and Jack cherished every one.

All this is to say that Milo Ventimiglia isn’t the first person who comes to mind when you think of a con artist. Yes, he appeared in two episodes of “Con Man” — Alan Tudyk’s meta 2015 web series about a sci-fi star clinging to fame — but the “con” in the title stood for “conventions” (and Ventimiglia was just playing himself). Sincerity can help sell a scam, but so long as the audience is in on the gambit, eventually they need to see just how good a liar the hustler can be. Typically, there’s a smile as reassuring as it is revealing (a la Danny Ocean), or a satisfied laugh after a job well done (few better than Paul Newman). Con artists live for the con, so they tend to take pride in pulling one over on their deserving marks.

Which brings us to “The Company You Keep,” Ventimiglia’s ABC’s hybrid heist-and-family drama, where he plays Charlie, a slick but small-time swindler who’s working on his biggest score yet. To most people, Charlie’s just a bartender at a Seattle dive. But to the audience, he’s a silver-tongued man of many faces — a pickpocket, a planner, and a loyal partner-in-crime. The latter descriptor suits Ventimiglia as snugly as Charlie’s custom tuxedo, and his physical skills as a charlatan come across well enough. But there’s no glint in his eye; he’s not having any fun while robbing the rich and disreputable — certainly not enough to justify dedicating his life to the job, as he’s apparently done for 40-odd years. Parts of Charlie are perfect for Ventimiglia — his loyalty to family and friends, his blue-collar cover story, his passion for a new flame — but “The Company You Keep” asks too much of its lead actor, and tries to do far too much itself.

You see, Charlie isn’t just a con man. He’s one-quarter of a con family. His mother, Fran (Polly Draper), and father, Leo (William Fichtner), are career criminals, and they’ve raised their two kids to follow in their footsteps. Charlie is the face of most capers, and his sister, Birdie (Sarah Wayne Callies), is behind-the-scenes running the op. Heck, when we first meet the Nicoletti family, Charlie’s fiancé is part of the crew — before she betrays them, leaves Charlie, and runs off with the $10 million score.

Her exit opens up the already crowded family-heist series to a third genre: romance. After losing his would-be wife, Charlie randomly meets Emma (Catherine Haena Kim) and, wouldn’t you know it, sparks fly. Emma just caught her boyfriend in bed with another woman, so she’s particularly receptive to a little ex-bashing and a lot of drinks. But what seems like a mutual rebound soon proves to be something more. They like each other. They share a connection. Maybe the timing is wrong, but they’re going to have to see this relationship through, for better or worse.

Courtesy of ABC / Scott Everett White

Too bad for the horny couple, “worse” seems inevitable. Emma works as a data analyst for a logistics firm — or that’s what she tells everyone because it’s generally frowned upon to walk around saying, “Hello, stranger. I work for the CIA!” Her family doesn’t even know what she really does, despite her brother running for the U.S. Senate as a successor to their papa, who recently retired from the now-open seat. While the Hills are none too happy about Emma’s lack of a husband, she can rest assured they won’t be prying into her career so long as her brother keeps all eyes on him.

Charlie doesn’t ask too many questions either, after being lulled to sleep by her purposefully boring explanation, but co-showrunners Julia Cohen and Phil Klemmer wisely stress that neither one of them is looking to talk about work. They see each other as an escape from jobs, from family, and from the general stress of their dangerous professional lives. Their attraction, while never as electric as the plot would have you believe, functionally ties the show’s two halves together: Charlie’s heist-driven half, and Emma’s crime-solving half. But then those halves are split into many smaller sections, where Charlie looks out for his family, Emma looks out for hers, Charlie goes to work, Emma follows close behind, and avenues for additional storylines spin out from there.

Their ongoing romance and family drama are squeezed inside episodes built around heists of the week, which make the initial two hours overloaded yet unsurprising. Perhaps it’s better for a broadcast series dependent on its two stars’ charisma to keep its options open, in the hopes that some dynamics will work better than others and the dead weight can be cut as the season progresses.

Still, “The Company You Keep” may not make it that far. Emma and Charlie’s perfunctory hook-ups aren’t lighting the screen on fire. They imply far more heat than they capture, and what’s glimpsed is blocked and captured too awkwardly to resuscitate Hollywood’s flailing sex life. Ace-in-the-hole supporting stars like Fichtner and Callies don’t have enough time to make a lasting impact, and the consistent presence of parents and siblings serves as a cold shower for any flickering flames. Glimmers of wit surface intermittently, lending some hope to a lightweight original in need of more attitude, but the series hues too closely to its straight-laced star.

While it’s nice to see Ventimiglia trying to stretch his range after his biggest role to date, “The Company You Keep” actually ties him further to family patriarch duties, without encouraging the actor to be playful, wicked, or anything but earnest. Heists are just more fun with a winking rascal at the helm, and Ventimiglia’s bad boy alter egos appear stuck in the past.

Grade: C

“The Company You Keep” premieres Sunday, February 19 at 8 p.m. ET on ABC.