Editor’s note: The below contains spoilers for the premiere of The Company You Keep.There are certain roles that just stick with an actor — the legacy of which can sometimes take away from any future roles they pick up. ForMilo Ventimiglia, he’s fresh off the heels of his iconic role onThis Is Usas Jack Pearson, a role he played for six seasons and one that earned him multiple Emmy nominations. He makes his return to the small screen with ABC’sThe Company You Keep, which is based on the South Korean television seriesMy Fellow Citizens!,and he has the challenging task of taking on a new persona less than one year after theThis Is Usfinale.
Yet the actor doesn’t miss a step in the show’s debut as it’s clear from the jump that he’s able to tap into not just his past role of Jack but also back to hisGilmore Girlsdays as the high school bad boy, Jess. His new character, Charlie Nicoletti, has the charm and the mystery of Ventimiglia’s past roles that make this transition seamless. It’s not always the case, but it’s pretty clear thatThe Company You Keepmade the perfect casting for their charming con man with Ventimiglia at the helm.

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What first put Ventimiglia on the map was playing Jess onGilmore Girlsfor 37 episodes across six years, as well as returning to the role for the reboot. It was there that he stepped into the boy who Lorelei Gilmore (Lauren Graham) didn’t want her daughter, Rory (Alexis Bledel) to see. A troubled youth, Jess first heads to Stars Hollow to live with his uncle, Luke Danes (Scott Patterson). It’s in this role that Ventimiglia was able to present himself as the mysterious bad boy with enough charm to keep Rory interested in him. While short-lived, their forbidden relationship featured plenty of ups and downs but was one that many fans had wished lasted longer, even hoping he’d be who she ultimately chose after the two had a touching, heartfelt interaction in the reboot.

When Ventimiglia steps into the shoes of Charlie inThe Company You Keep, there are shades of Jess that come out in his actions as a con man, especially towards the end of the first episode, when he arrives on a motorcycle donning a leather jacket to see Emma Hill (Catherine Haena Kim) andexpress his feelings towards her. It’s straight out of the Jess playbook — and for fans ofGilmore Girls, a scene that unfolded in the fourth season when he tells Rory that he loves her, same attire and all.
‘This Is Us’ Is Where Ventimiglia Became Infectiously Charming
There were plenty of stops in between, but it was Ventimiglia’sThis Is Usgig that introduced him to a whole new audience and allowed him to become America’s favorite Dad throughout the show’s decorated run. This was where Ventimiglia used his charm to win over the viewers with each scene he stepped into, offering up words of wisdom as both a husband and a father all while pulling at the audience’s heartstrings with every chance he had.
When it comes to playing a con man inThe Company You Keep, there was no doubt he had that brooding, secretive angle covered — but to present a convincing Charlie, he has to be captivating. It’s surreal to see him take this new opportunity and so effortlessly play a believable bad guy who also is someone who could fall in love with an undercover CIA agent. Yet, what he demonstrates inThis Is Usis that he’s more than capable of winning over our hearts, and it doesn’t take long for this new slick-talking character to do the same here. There is some smooth, elegant banter between him and Emma at the bar during their first encounter that instantly provides insight into where this story is heading. No one could blame Emma, someone who is said to be a good judge of people, for falling head over heels for Charlie; after all, Ventimiglia has been winning the audience’s hearts for decades now.

‘The Company You Keep’s Charlie Is a Con Man We Can Root For
There’s been quite a movement lately in being able tocheer for someone who’s doing something bad. While Ventimiglia’s character is certainly not on the level ofPenn Badgley’s Joe Goldberg inYOU, he’s yet another person whose mischievous and illegal adventures won’t deter fans from falling in love with him. It takes a particular caliber of acting to be able to pull this off, so what Ventimiglia can accomplish in just one episode is remarkable. This is his most ambitious role to date, so it’d be understandable if there were some speed bumps along the way. There’s quite a bit of complexity with a character like Charlie, someone who has to not only pull off being a believable con man but have enough suave and allure to win over Emma and be human enough that his family’s storyline, which centers on them being con artists running a bar as a front but also ready to put it all behind them, also strikes a chord with the viewers. From the moment he steps onto the screen, pulling off a card trick with his sleight of hand, Ventimiglia makes it a point to deliver with each line and expression so that nothing takes awayfrom this unorthodox love story.
The Company You Keepwill only go as far as its two leads go, and the early signs suggest both Ventimiglia and Kim were quick to develop chemistry, an essential part of making this narrative work. There also doesn’t seem to be any doubt that Ventimiglia is the right guy for the job. Viewers should be in for a treat as he makes this role his own and continues to add layers to this new show all while pulling from his two most impactful characters, both of which exhibit unique qualities that translate into the DNA of Charlie.
The Company You Keepairs on ABC at 10 p.m. ET on Sunday nights and is available for streaming on Hulu.