The Unconventional Secret To Milo Ventimiglia’s Success

Milo Ventimiglia
JACKET AND TOP: Ermenegildo Zegna

Photo Credit: Mark Squires

… IS KINDNESS.

BY LAURA SCHREFFLER
PHOTOGRAPHY MARK SQUIRES
STYLING ILARIA URBINATI
GROOMING BARBARA GUILLIAUME

Milo Ventimiglia
JACKET, PANTS AND TOP: Ermenegildo Zegna
WATCH: Rolex

Photo Credit: Mark Squires

NOT MANY PEOPLE would dare to take an Airstream up to 90 miles an hour, but Milo Ventimiglia, believe it or not, has always had a bad-boy side. Still, the truth behind his need for speed is much more Milo the man and less, perhaps, the rebel many used to make him out to be. He tested the limits of his 55 mph chrome caravan because he was hell-bent on getting to work on time. And that, too, is badass, though perhaps not in the conventional way. Which is okay, because conventional Milo Ventimiglia is very much not.

Fans typically correlate him with one of two roles: Jess Mariano, Gilmore Girls’ rebel without a cause, or, more often these days, his current small-screen character, Jack Pearson, the flawed but fantastic dad of three on NBC’s This Is Us. The truth? He’s somewhere in between.
The Milo Ventimiglia of today, a man on the brink of turning 44, toes the line between these two amalgamations. He has a thing for Harleys and favors leather jackets like Jess; like Jack, he is kind, responsible and paternal — an intriguing trait for a perpetual bachelor. Call it the best of both worlds.  

But let me backpedal here and set the scene for how Ventimiglia came to be speeding across the U.S. of A. in his big silver bullet. Last spring, he was about to start filming Evel, a limited series about daredevil Evel Knievel, in New Mexico. His transformation was complete: a lush, dyed-blond mane, blue contact lenses, a waddle, thatches of tufty chest hair. He learned to do wheelies on vintage motorcycles; no hardship, pure fun. And then, on March 13, two days before production commenced, Covid-19 shut it (along with the rest of Hollywood) all down.

After hearing about the panic and the toilet paper wars back home in Los Angeles, he opted to stay in Albuquerque for three months. His rented house was already paid for, so why not? He hunkered down and chilled out. With Hollywood still shuttered months later, realization dawned that the road trip he had been attempting to take for the better part of three years, the one he never seemed to have enough time for, could finally happen. So he took a Covid test, headed to his hometown of Anaheim, Calif. — which also happens to be the home of Disneyland and Great Adventure (so fitting) — to give his mom and dad a hug and made tracks.

“There was no obligation to be on set, which meant that I could be anywhere,” he explains to me over Zoom in March. “So I said, ‘You know, I’m just going to go on the road for a little bit.’”

That “little bit” turned into a 10,000-mile adventure: a pitstop in Utah to visit one sister, a journey to Oregon (where he also owns a home) to see the other, some camping in between and the purchase of his hot new ride (that Airstream) — which, though it sounds so “f—ing chic and cool,” was a pretty big departure from a Harley, his transportation of choice. (And it was definitely preferable to that one time in the past year that he took a flight, double-masked, shield up, hoodie pulled tight, looking like some kind of “weird video game character.”)

Ventimiglia would have kept on going, too, if duty hadn’t called. “I was just taking the southern route, and my plan was to go out to Georgia, hang a left and go up the Eastern Seaboard, and then come back across the Dakotas and whatnot, go back through Montana, Idaho and Oregon again and drop back down. But then I got called up again on This Is Us, so I was like, ‘Oh, all right. Let me just turn around and take the fastest road I can to get back to California.’ So that’s what I did.”

Milo Ventimiglia
JACKET: Dolce & Gabbana
T-SHIRT: The Optimist
PANTS: Basic Rights
BOOTS: Kurt Geiger
WATCH: IWC

Photo Credit: Mark Squires

He didn’t haul ass the entire way — he stayed mostly within the confines of the trucking and trailering limits of 55 mph — but yes, there were moments when the gas pedal became his best friend. (This might explain why he has temporarily traded in his slow ride for a swifter one: He arrived at our photo shoot in the new BMW M8 Competition. Coincidentally, he had just shot a commercial for the brand’s M4.) And if he had truly been running late? Forget about it. He would have done whatever it took to make it to the set on time for the September 19 start date. People were counting on him, after all. The Rolex Submariner he’s currently wearing — which is engraved with This Is Us and his initials — serves as a pretty stellar reminder.

For seven out of every 12 months for the past five years, he has lived and breathed This Is Us, the tearjerker tale of the Pearson family — Vietnam War vet Jack; his wife, Rebecca (Mandy Moore); and the Big Three, biological twins Kevin (Justin Hartley) and Kate (Chrissy Metz) and adopted son Randall (Sterling K. Brown) — which time-hops between the 1970s and the present day. Ventimiglia plays Jack Pearson poignantly. He struggles with his own demons as a recovering alcoholic, but he prevails in the end, managing to wrestle them to the ground for the greater good of his family. Ventimiglia has accrued a substantial cult following, endless adoration and three consecutive best actor Emmy nominations as a result.

Yet his character has been dead for three seasons (which is a weird statement only for those who haven’t seen the show).

Surprisingly, Jack’s death wasn’t as traumatic for Ventimiglia as you might expect, given how much chronic weeping the series invokes in its viewers. “I always knew that the character in the present day was gone, and because I knew that he was gone, I just played him ‘as if’ and focused on exploring younger Jack — Jack in Vietnam, Jack falling in love, Jack kind of reimagining who he is, being a veteran of war. I always knew we had a lot of latitude to travel with him, and there was going to be a lot to explore. I also knew that at a certain point, just given science, the kids were going to be growing up, and we had to age with them.”

So it might be the beginning of the end for the hit series, which reaches 8.2 million viewers per week in its fifth season. “That’s what we’re hearing, so I guess you could say ‘last season-ish,’” Ventimiglia tells me. “Dan Fogelman, our show’s creator, always imagined fewer episodes than that, but given the broadcast schedule, [the network] wants 20-some episodes a year, as many seasons as you can get. But with that, creatively, we run into problems. I mean, my character is dead, [and because of the timeline changes] the younger actors who play our kids are growing up and bumping against the ages of the actors who play the same characters as teenagers. So it’s kind of like, well, which one do you choose? There are a lot of roadblocks creatively that the writers just can’t get around. I mean, they can do tons of visual effects to make me look like I’m in my 20s, but we can’t make growing 13- and 14-year-old kids look like they’re 8 again. It’s like reconciling quantum physics or something. Time marches on, and we really can’t hold it back.”

He pauses, then laughs. “Do you remember that photograph in Back to the Future that Marty McFly has, where his sister and brother start to disappear, and then he starts to disappear? I feel that way with Jack. There’s a version where we’re running out of runway with stories that we’re telling for him, but it doesn’t mean that Jack’s story can’t support a Kevin story or a Randall story or a Kate story or a Rebecca story.”

If the next season is to be the show’s last, the beginning of the end is imminent. The fifth season will wrap this week, while the sixth is slated to start shooting this summer, coronavirus restrictions withstanding. And though his storyline may be supporting the others, Ventimiglia is adamantly not done with Jack — or the show — just yet. In fact, he’s exploring new challenges by directing his second episode of the series; “Jerry 2.0” will air on May 18. The show has provided him a platform to grow, with it as well as within it, and he wouldn’t change that for the world.

“I love my job, and I love my crew. We’ve got a great cast, and they’re all wonderful people,” he says, adding, “I’m doing the show as long as they’ll have me, and I think I’ll be on it as long as the show’s on.”

Milo Ventimiglia
SWEATER: Todd Snyder
PANTS: Brioni
WATCH: IWC

Photo Credit: Mark Squires

BEFORE MEETING VENTIMIGLIA, I get the lowdown. The truth is uncomplicated: above all else, the guy is just so f—ing nice.

And the thing is, I want him to be nice. You want him to be nice. After all, he plays the GOAT of TV dads. It would be a crying shame if he turned out to be a jerk.

When I ask him if he would describe himself this way, his mouth curls into his signature lopsided smile, the result of dead nerves in his lower lip. “I crack a joke sometimes and say, ‘What I lack in talent I make up for in being nice.’ So hopefully people just want to be around me for that working purpose.”

He’s being modest, but his comment is also accurate. He’s the kind of person who makes everyone feel special, who pays it forward without expecting anything in return. It’s not an act. He’s the real deal.

An example: he spent the last few months commuting between Los Angeles and Orange County to take care of his parents. His Vietnam War veteran dad, Peter, “broke his leg out of f—ing nowhere,” and his mom, Carol, is in cancer remission. “All of a sudden, baby boy has got to go down and do a bit more for them,” he says, noting that this is why he’s already received Moderna’s Covid-19 vaccine. But more important, he has always tried to see them as much as possible (or as much as his work schedule allows). “My parents only live 45 minutes away from me, so I try to go and see them as much as I can, but that’s not always the case. Sometimes I’m like, ‘Hey, Mom and Dad, I’ve got two hours on a Sunday morning. Can you guys come up to L.A. and just hang out for a minute quietly, because I’ve been talking all week and I just want to sit with you?’ And they do. My mom and dad are the best. They’re incredible people.” 

This inherent loveliness is why Ventimiglia is close with his castmates, and even closer with the crew. In fact, he’s kind of like — wait for it — the dad of the production…even when the show is not technically in production.

“I would check in on random people over the break. Like, I’d call one of my electrics, who had a hip replacement. ‘Hey, Tony, how’s the hip? How’s Billy doing? Oh, Billy’s good? Okay, cool. Just let the boys know I’m thinking about them.’ I’d check in on people, just so we all find a way of keeping connected.” This, of course, includes costars Brown, Metz, Hartley, Moore, Chris Sullivan (who plays Kate’s husband, Toby) and Susan Kelechi Watson (who plays Randall’s wife, Beth). He likens this tight-knit crew to the family you leave behind when you head to college for the first time: you know they’re always going to be there for you, and that you’ll always make your way back to them.

On set is no different. He shows up on his days off, often with a camera in hand to play unofficial cast photographer. He is a cheerleader, waiting in the wings to offer support during critical scenes. And he is always there to celebrate the endless hours that the 300-plus-person crew put in. “I try to boost morale and make sure everyone’s feeling good, and when we’re on set, spoil them with food trucks and coffee trucks and all that. And Mandy is right there with me. There are usually a lot of messages and gifts from Mom and Dad,” he confides.

And in his opinion, that’s the way it should always be, especially when your name is the first on the call sheet. Sure, its purpose is to organize the schedule, keep the cast and crew accountable, but for him, it’s a responsibility that he takes very, very seriously. “I’ve got to make sure I do my job, but in addition to that, I’ve got to make sure the tone on set is fun and that everybody feels welcome, everybody feels their place of contribution to the making of the show, for the morale of the group.”

Not that it would make much difference if he was number one or number 20: he treats everyone the same regardless of his rank, or theirs. “I’m always just there to make people laugh and feel good, hopefully.”

This sentiment extends far beyond his This Is Us family. Ventimiglia uses his celebrity status to give back to a plethora of philanthropic organizations in a very hands-on way.

Milo Ventimiglia
JACKET AND TOP: Ermenegildo Zegna

Photo Credit: Mark Squires

In 2019, the year before the world went to shit, he was circumnavigating the globe, stopping in Kenya with the Red Nose Day campaign to end child poverty. Immediately afterward, he traveled to Washington, D.C., to hang out with military vets like his dad and meet current Defense Department employees at the Pentagon to discuss a stronger military-civilian connection. And I haven’t even mentioned the United Service Organization (USO) tours he’s been doing for over a decade, the most recent of which was a 10-show, six-day holiday tour across Europe in December 2018 to bring deployed servicepeople some holiday cheer. There aren’t many folks who would actively set foot in hot zones like Kuwait, Iraq and Afghanistan, but Ventimiglia has never shied away from an opportunity to help others.

“I’ve been in the business for 25 years, but it’s not lost on me, the position that I have in a public sense, in a social sense, because of what I’ve done in front of the camera. So what I like to do is use that for good. If I can impact someone positively just by smiling at them or acknowledging them, seeing them, that’s great. I find it so much easier to smile at someone, so much easier to be kind to someone — and not just do it because I expect it in return, but just to put good out into the world,” he says, adding, “I can’t only think of myself. I’m always thinking about everyone else. That’s just the way I’m built. I take everybody and everything into consideration.” 

And sometimes, that’s been to his detriment.

“I definitely would put people before me all the time, and I think people took advantage of that when I was younger. I wasn’t a carpet to be walked on, but I think I spent so much time trying to make other people happy that I really forgot how to make myself happy. Then I started to understand, ‘Well, if I can fill myself up and make myself whole, then I can actually provide for others.’”

He came to this conclusion when he reached his 30s, when he had already been acting for more than a decade (having made his debut on The Fresh Prince of Bel-Air in 1995), with TV projects like Gilmore Girls, American Dreams and Heroes as well as films like Rocky Balboa (playing Rocky Junior) under his belt. “I went through a breakup and then kind of rebelled a little bit — my own version of rebelling — which I don’t even know how to describe. It just felt like a rebellious time. And then I kind of had this moment where I was like, ‘Wait a minute. I’ve done well in my career. What do I want to do? How do I want to grow and see my career grow? What do I really want to present to the world?’ And I just figured out that I’ve got to be happy and do things that I want to do. Even if there’s something I don’t want to do, it doesn’t mean I have to be a jerk. I can politely say no, thank you. I’ve actually gotten really good at saying no. If I’m invited somewhere and don’t really want to go but feel obligated, [in the past, I’d have gone]. Now, I can say, ‘Thank you very much, but I can’t. Thank you. Thank you.’ Literally, I’ll keep saying thank you until people kind of get it. I didn’t want to run myself ragged being in service to so many different people. So I got to a point where I was like, ‘I’ve got to make sure that I’m focusing on myself and looking out for myself, and with that, I can be truly available to other people.’”

Around the same time, he came to another realization: his career had to come first. “Everything is second position to work — everything. I’ve had friendships and relationships that definitely had a hard time with that. I’d get home from work and a girlfriend would want to spend time together, and I’d have to make sure I did spend time with her, sit down and eat, maybe turn on a movie for 20 minutes. But when my bowl is empty, I’ve got to go into my office and close the door and work for another two hours so my lines are spot on and I’m ready to be on set the next day, so I’m not wasting time for the crew. You kind of have to dedicate yourself to it in a greater way, and some things are going to be sacrificed while others can run concurrently.”

So he gets it when the situation is flipped; he doesn’t get upset when a date has to be postponed or a friend cancels plans. “This has very much led me to be accepting when friends and romantic relationships have things that are important to them. It’s like, ‘Yeah, go do that, I understand.’ You have to give someone room to live their life to their fullest, and hopefully those two lives can just run on the same track.”

Milo Ventimiglia

JACKET + PANTS: Dolce & Gabbana  
T-SHIRT: COS 

Photo Credit: Mark Squires

WITH HIS YOUTHFUL good looks (which he credits to genetics and, “let’s be honest, f—ing boring things” like his diet, beauty sleep, and not drinking or doing drugs), penchant for motorcycles and bachelor status, Ventimiglia reminds me of a young George Clooney. At 43, there’s something boyish about him, yet he’s very distinctly a grown-ass man. The dinner he describes making the night before our conversation — mac and cheese, but an elevated mac and cheese — just serves to punctuate this point.

His process was definitely labor-intensive, or at least more work than ripping open a box of Kraft. He shares his process step-by-step, saying, “I cooked the pasta and drained it, running a cold bath on it real quick to stop the noodles from cooking and to keep them firm. I put cream cheese inside the hot pot and let that kind of milk up a little bit before throwing the pasta back in with just a touch of ghee to give it a different taste other than just butter, and then I put the powdered Annie’s mix on it with some smoked salt on top. I made it a little fancier. I also had an arugula salad with a truffle oil dressing that I made, and a sweet potato that I forgot at home because I was going to bring it to work today. Damn.”

When I tease him about his gourmet take on the ultimate frat-boy food, he laughs. “Motherf—er said truffle oil? What an asshole!” But in all seriousness, the dude can cook (even if he does prefer Postmates for ordering food when his parents come to visit). Survival of the fittest and all that. “I mean, I’m a 43-year old single guy, you know. I’ve lived on my own for 25, almost 26 years.”

His home for the past 20 years has been the west Los Angeles suburb of Mar Vista, once the sleepy kid sister of Venice, which has blossomed into the hub known as Silicon Beach. Not that he spends much time there — Ventimiglia is a busy guy. When he’s not working on This Is Us (he has a 5 a.m. start time, with hair, makeup and daily Covid-19 tests, plus 12 hours of shooting daily) or traveling, he’s making films like the romantic comedy Second Act with Jennifer Lopez, Grace of Monaco with Nicole Kidman and The Art of Racing in the Rain with Amanda Seyfried, as well as putting in endless hours with his production company, DiVide Pictures, which has produced projects like the dramedy Relationship Status, web series Chosen and two comic books with Top Cow Productions, among other ventures.

In addition to shooting season six of his hit show, he has bigger plans for directing in the future. “That’s always been a goal, to direct more. But every time I’d line up a directing gig, I’d get an acting gig. The acting gigs pay more and are a little shorter timewise. But as my career marches on and I’m able to maybe be a little more selective, then I’ll have a little bit more time to focus on directing,” he says.

He’d also like to see the Evel Knievel series get off the ground, though he’s aware this might not be the right time. “Corona kind of kind of killed it for the moment, and hopefully it will be back, but it’s kind of tough with the state of the world to bring back a character like that,” he muses. “He did a lot to inspire people, but he really wasn’t the best guy. I think if anything, we’d be telling the story as a bit of a cautionary tale, like be careful who you exalt to hero status.” (This turn of phrase strikes me as being particularly apt, given that one of Ventimiglia’s most famous roles was playing superhero Peter Petrelli on NBC’s Heroes.)

In the meantime, he’s not losing sleep over it. His life is too full to do otherwise. In addition to his plethora of projects, he’s back in school, after a six-year hiatus, to learn Japanese. “Japan is always my travel go-to. I love Japan so much that I started going to school to learn the language, to read, write and speak. Part of me feels like, yes, I’m getting a practical skill, being able to communicate. But also, I feel like I’m learning art.”
If anything, the last year has taught him to take advantage of the time he has versus the time he doesn’t, to focus on the things he loves and to continue to live his life the way he lives it: unapologetically, but nicely.

“The last year reaffirmed my life a little bit,” he says. “I came to the conclusion that I’m just going to continue the way I live, because the world needs it. Maybe if someone picks up on a positive attitude and they hang on to that, and their next interaction becomes positive when it could have been a shit show, well, that’s good. It sounds very simple, like Forrest Gump simple, but it’s true: do what makes you happy. It’s definitely a hard lesson that I had to learn. I’ve had friends in my life — my closest friends — finally say to me, ‘Hey, Mi, you’ve got to live your life, the version of the life that you want to live. Don’t make excuses or feel the need to justify anything to anybody.’ We are all deserving of having control over our own lives, the direction of our own lives and being to have happiness, success and companionship.”

And there you have it. Nice guys — truly nice guys — don’t always finish last, nor do they always put others first. They do the best they can and try to be the best version of themselves they can possibly be. In fact, I think that’s what we’d call “winning.”

Milo Ventimiglia
JACKET AND TOP: Ermenegildo Zegna
WATCH: Rolex

Photo Credit: Mark Squires

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