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. 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. 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. The latter descriptor suits Ventimiglia as snugly as Charlie’s custom tuxedo, and his physical skills as a charlatan come across well enough. But to the audience, he’s a silver-tongued man of many faces - a pickpocket, a planner, and a loyal partner-in-crime. To most people, Charlie’s just a bartender at a Seattle dive. ![]() 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. Con artists live for the con, so they tend to take pride in pulling one over on their deserving marks. 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). 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. 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). These were the times that mattered, the times worth remembering, and Jack cherished every one.Īll this is to say that Milo Ventimiglia isn’t the first person who comes to mind when you think of a con artist. 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. Peter also approached his responsibilities with purpose, and you know Rocky Balboa’s kid gave it his all. 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. Jose Perez/Bauer-Griffin / GC ImagesĮarlier this year, Sherman-Palladino and Palladino - who worked with the actor on “Gilmore Girls” - told TODAY about seizing the opportunity to bring back Ventimiglia.‘Barry’ Enters a Strange New World - and Can’t Shake the Old Oneīut even after Ventimiglia made the leap from adrift adolescent to assured adult, one uniting factor remained: earnestness. Rachel Brosnahan and Milo Ventimiglia are seen on the set of "The Marvelous Mrs Maisel" on Jin New York City. However, their one-night stand was interrupted by “Handsome Man’s” wife - and that was the extent of his appearance. The two would then go on to flirt and have long conversations, before taking things to the next level. ![]() He meets Midge while casually walking in Central Park. Ventimiglia’s character appeared in episode seven of the Amazon Prime show's fourth season. “We will see a nice, more extensive Part 2 to ‘Milo and Rachel,’” Palladino revealed, adding that viewers will “find out his name” in the upcoming episodes. In a new interview with TVLine, creator Amy Sherman Palladino and writer Daniel Palladino confirmed that Ventimiglia would be making an “extensive” appearance in the show's fifth and final season.
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