Milo Ventimiglia This Guy InStyle

Milo Ventimiglia Is Ready for Action

The This Is Us star is trading in his Terrible Towel for a Negroni in his new series, The Company You Keep.

Milo Ventimiglia has finally found a character as unremarkable as he is. His words, not mine. Capturing the heart of Rory Gilmore — and the hearts of millions of teens across the world — in his 2001 breakout role as Jess Mariano on Gilmore Girls and later capturing the hearts of America as Jack Pearson on This Is Us, Ventimiglia’s newest character touches on his longest con yet: remaining completely elusive. 

Not a stranger to action-based television dramas (see: Heroes and Chosen), Ventimiglia looks at home on the set of The Company You Keep. As he walks onto Stage 2 at the Paramount lot for his photoshoot with InStyle, you can sense how closely he holds the responsibility of continuing the legacy the space carries. He tells everyone about the history of the stages he’s filming on, explaining how the low ceilings make it complicated for lighting and sets. As the conversation moves on to the various offices on the lot that used to be occupied by film greats like Alfred Hitchcock, a large structure built to resemble a dimly lit dive bar towers behind him. It’s there on Stage 1 (where Star Trek: The Original Series and The Truman Show once filmed) that Ventimiglia’s current role comes to life. 

Milo Ventimiglia This Guy InStyle
Barbour jacket. Levi’s sweatshirt. Ermenegildo ZEGNA trouser. Brunello Cucinelli belt. London Sock Company socks. Tod’s shoe. Rolex watch.

Alex Harper

Milo Ventimiglia Polaroids


Charlie Nicoletti, grifter by day, bartender by night, runs a con operation out of his Baltimore-based bar with his parents and sister in ABC’s upcoming series The Company You Keep, which premieres on Feb. 19. 

The “family business” gets him stuck in a precarious situation very early on, setting off a series of events that leads him to a romantic weekend spent with Emma, played by Catherine Haena Kim (FBI) — who also happens to be a CIA agent investigating an Irish crime syndicate that recently fell victim to one of Nicoletti's cons. It’s a wonderfully messy twist of events that presents Ventimiglia with a new arena far, far away from idyllic Stars Hollow and the quaint suburbs of Pittsburgh. It’s something Gilmore Girls and This Is Us fans will be surprised to see. 

With an inherently chameleon-like charm, Nicoletti’s nature is to fit in. This quiet, under-the-radar characteristic is not only what drew Ventimiglia to the role, but also something that he finds to be similar to the balancing act he performs daily as an actor and public figure.

“I like to describe him as unremarkable, unmemorable, but that's just who he is when he's existing in life,” he explains. “He has got to live these extravagant lives, reflecting people. And I think that's similar to an actor. I try to be unremarkable myself. I try to keep things limited to what people know about me ... just so that when they're watching a character I'm playing, they're seeing the character. They're not seeing me dressed up. They're just like ... Jack is alive. Jess is alive. Charlie is alive.”

Nicoletti is indeed alive, despite the many attempts on his life throughout the series. And Ventimiglia is barely making it out unscathed himself, explaining that he’s already split his eyebrow open and wears a knee brace to keep up with the action sequences.

“It's funny. When I signed up for this, I thought it was going to be a lot of words,” he jokes.

This departure from his signature family dramas is what piqued Ventimiglia’s interest in the role. But it wasn’t just the action-packed episodes or the cons that lead him here. It’s a sense of familiarity that ties him back to Charlie. 

“I think it was just more about doing something different than Jack. Finding a character that's not a father, finding a character that's not a husband, finding somebody who's still looking for that complement to his life, in a partner, romantically,” he explains. Kim complements him perfectly as Emma — the alluring-yet-cunning counterpart to Nicoletti’s charming and deceitful M.O.  

Milo Ventimiglia This Guy InStyle
Barbour jacket. Levi’s sweatshirt.

Alex Harper

Kim brings the same magnetic appeal from her character on FBI to her role on The Company You Keep — which Ventimiglia describes as a mashup of “Out of Sight meets Ocean's Eleven meets The Americans” and is based on My Fellow Citizens!, a popular South Korean comedy. She also brings with her another, equally important quality that Ventimiglia credits as being a huge help to becoming Charlie. 

As a con man moonlighting as a bartender, you’d need to know how to make a drink. Specifically, Charlie Nicoletti’s drink of choice: a Negroni. Luckily, Kim had him covered.

“I don't really drink,” Ventimiglia admits. “Catherine used to bartend. So, in the scenes where Charlie's teaching Emma how to make a Negroni ... Catherine had to teach Milo how to make a Negroni first.”

And while the entire population of House of Dragons fans on the internet could also assist in this lesson, Ventimiglia would never know that. A few people on the set laugh at his blissful ignorance of social media snafus when the Negroni Sbagliato makes its way into conversation. If The Company You Keep is responsible for further continuing the online discourse of the popular Italian drink, Ventimiglia has nothing to add to the discourse. His non-alcoholic con-man drink of choice would be “something clear with bubbles.” And he leaves it at that.

Milo Ventimiglia Polaroids


Instead, Ventimiglia’s social media presence is much more subdued and confined to travel photos and the occasional selfie. He credits his off-screen lifestyle to be the most romantic thing he can do for himself. Well, that and his skincare routine: “Moisturize. You have to.” 

Eagerly jumping in to help the photographer on set load her camera with film – discussing a particular brand of Japanese film he loves to use and even snapping a photo in the process – it’s clear Ventimiglia has an appreciation for the medium. The thrill of lining up a shot on a camera mixed with his love for the history of the places he visits presents fans with a look into his life when he’s not in front of a camera or on a large sound stage. It is as if you’re standing next to him on a cliff in Gruyere, Switzerland, or sitting next to him, admiring the vastness of Joshua Tree National Park. With each post, he curates a travel diary that seems almost too intimate for the general population. 

“You have to start within yourself, and find your worth, and find what makes you happy,” he says. “Find the activities that make you happy and go do those things.”

Eventually, Ventimiglia postulates, this self-acceptance and internal work is what helps lead you to the right people — soulmates, if you will. A person who most likely exists in this world, but not until the work is done on your end to cultivate that type of relationship. 

Milo Ventimiglia This Guy InStyle
Irish Crone sweater. Todd Snyder jeans. Ralph Lauren belt. Kurt Geiger boot. London Sock Company socks. Rolex watch.

Alex Harper

“I'm sure we're all bound in the universe in some way ... energetically crushed together and pulled apart, ripped apart,” he says after admitting everyone, including himself, is searching for that one person in life. “We're all trying to find partnership. We're all trying to find that person that can put up with our shit. But I think there's got to be something more behind the scenes working that would actually kind of put two people together and make it work. Penguins choosing each other, things like that.”

For now, he’s focusing on himself. Asking for help when he’s struggling and seeking advice from others along the way. However, when it comes to the love department, Ventimiglia is cautious to draw any advice from his most iconic characters.

Jess Mariano is deeply embedded in our hearts and minds as one of the O.G. internet boyfriends. But to the disappointment of the prospering Gilmore Girl fan base still religiously posting on Tumblr, Ventimiglia doesn’t really think about him at all. I mean, who can blame him? While some can still clearly picture a fresh-off-the-bus Jess, staring out over Stars Hollow for the first time from the steps of Luke’s Diner set to “This Is Hell” by Elvis Costello ... it was over 20 years ago. 

Milo Ventimiglia Polaroids


“Jess was a child,” Ventimiglia says. Twice. When it comes to love and relationships, he confirms what many struggle to come to terms with: Jess Mariano is not the blueprint for anyone’s boyfriend — whether it be on the internet or real life. And he means it in a mostly positive way. 

“I think Jess had a lot of life to live. And I don't think he was quite set up the best way in his younger years — not having a father, not having a parent. He had to find his way on his own a little bit,” Ventimiglia explains. “And I think he got to it a little quicker, just a place of ... acceptance of who he was, and what he wanted to be, and who he wanted to be around.”

Begrudgingly tucking away a 1,000-word take on why Jess Mariano is arguably Rory Gilmore’s best boyfriend for that exact reason, it is easier to admit that his second-most-notable character is one that truly embodies the ideal boyfriend. So much so that in 2016, Ventimiglia graduated from internet boyfriend to internet husband. With an ‘80s mustache added on top.

Jack Pearson walked into our lives wearing nothing but a Terrible Towel and sent everyone into a frenzy, ushering in a new wave of fans. A dedicated father and husband, Pearson quickly became America’s dad. His untimely death by Crockpot — a plot that took 32 episodes of This Is Us to reveal — weaves in and out of his family’s lives as they grow up to become parents and spouses themselves. However, Ventimiglia remains more detached from his character than one might expect. 

Milo Ventimiglia This Guy InStyle
Barbour jacket. Levi’s sweatshirt. Ermenegildo ZEGNA trouser. Brunello Cucinelli belt. London Sock Company socks. Tod’s shoe. Rolex watch.

Alex Harper

Milo Ventimiglia Polaroids


Not a father himself, he pulled his inspiration for Jack Pearson from the father figures in his own life — similarly to how he based Jess Mariano on a childhood friend. Always the “attainable hero,” as Ventimiglia refers to him, Jack had an impact on people who tuned into the show weekly to be comforted and consoled by its aspirational family values. 

“This is someone that we can all strive to be,” Ventimiglia explains. “It goes beyond just men, women, old, young — any background. It's like, ‘Let's just strive to have a golden heart.’ We all have our hang-ups. We all make our mistakes. But fundamentally, who Jack was? He was just a good, solid man.”

It’s this embodiment of selflessness that Ventimiglia sees as a lasting impact of his time spent on This Is Us. Sure, there are some parallels between Jack and himself. “I think both of us are not without our faults, but we always do our best, try our hardest,” Ventimiglia explains. But the thing he misses most about playing Jack Pearson? 

Mandy Moore,” he states without hesitation, causing the room to break out into awws. “I miss my friend.” 

While Moore and Ventimiglia are both working on new shows (she is executive producing and starring in Hulu’s Twin Flames), they also find themselves on opposite coasts — Moore filming in New York and Ventimiglia in Los Angeles. They keep in touch despite the distance. 

“We've recently sent some messages back and forth,” Ventimiglia explains, eliciting more quiet awws. “I was checking in on her and her husband, and the babies, and whatnot, and she [was] checking in on life over here.”

While the romance of Jack and Moore’s character, Rebecca, may not have swept Ventimiglia into his feelings, it seems that departing from the cast and its crew certainly did. To the extent that when Ventimiglia returned to the Paramount lot for The Company You Keep, he brought the This Is Us crew with him, noting that he doesn’t have to miss them as much — just Mandy Moore. 

Spending five days a week on set, you can see how much of Ventimiglia puts himself into his productions. He pauses throughout his shoot and interview with InStyle to make sure those around him are getting what they need — most of the time to acknowledge the crew by name as they pass. In those sudden pauses, he never misses a beat and picks up the conversation right where it had left off. A professional, sure, but most certainly a mark of someone who is anything but unremarkable. 

Read on to learn more about Ventimiglia’s favorite music, his take on astrology, and just how much he loves a sweet treat. 

Milo Ventimiglia This Guy InStyle
Cotton Citizen T-shirt.

Alex Harper

Favorite place you’ve visited?
Japan. I studied a lot of Japanese culture and history when I was a kid. I spent quite a bit of time there and started learning the language and everything. I got so into it. 

Is there a place that you've never been to, that you'd like to go?
The moon. 

Do you have a favorite joke to tell?
It’s too dirty to tell.

If you were to spend $1,000 in a day, what would you buy and why?
Probably food. But not for me. [I’d] walk into a Sweetgreen and buy everybody salad. 

First album you owned?
Nevermind by Nirvana. 

Favorite cheesy pickup line?
God ... I would always just walk up and introduce myself. It's not cheesy. That's the thing. It's just direct. Just, “Hey.” Start from a good place.

What's your go-to coffee or tea order?
Hot matcha, plain with honey or coffee with oat milk and honey.

What’s your favorite food?
Sweets, which is trouble. But it keeps you going when you're shooting long hours. 

Any sweets in particular?
Chocolate. Cakes, cookies, danish. Donuts, popsicles, pie. A lot of pie with ice cream on top. [You] could even put a slice of cheese [on top] if you want to add a little bit of salt on top of your pie. That one is for my mom.

Favorite genre of music?
I grew up on the Smiths. I grew up on a lot of ‘70s rock. Led Zeppelin, Stones, Jimi Hendrix, all that. [I] kind of go back to it a lot. 

Favorite bagel order?
Easy. Sesame bagel, scooped, with cream cheese, and either tomato or cucumber. But then you have to put seasoned salt on top of it. 

Favorite book?
There are a couple books that I read once a year. The first one is a book called Replay by Ken Grimwood. I'm always shy to talk about it, because I hope they never make the movie, although there's a really good script of it right now. But it's just a wonderful book about a man who's living his life over and over and over and over again. 

The other one is written by a guy named James Frey. It's called The Final Testament of the Holy Bible. It's about the second coming of Christ, but it kind of takes the whole concept and puts it on its head. It's a very beautiful story of love and loving people entirely.

Do you believe in astrology?
I have fun with it. Born in July. Definitely Cancer: I can get crabby and [have] organized piles of things around my house. When it's a full moon, I'm just kind of staring at it. And I think that's kind of a thing with Cancers; I'm kind of ruled by the moon. I think there is probably some kind of accuracy and a little bit of magic that comes with it — and I think everybody needs a little bit of magic.


  • Photographer
  • Alex Harper, assisted by Bailey Clark

  • Videographer
  • Brandon Scott Smith

  • Stylist
  • Ilaria Urbinati

  • Special Thanks To
  • Polaroid

  • Senior Editorial Director
  • Laura Norkin

  • Creative Director
  • Jenna Brillhart

  • Senior Visuals Editor
  • Kelly Chiello

  • Video Director
  • Justine Manocherian

  • Fashion Direction
  • Samantha Sutton

  • Associate Photo Editor
  • Amanda Lauro

  • Assistant Camera
  • Derek Sullivan Smith

  • Executive Producer
  • Bree Green

  • Booking
  • Talent Connect
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