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Milo Ventimiglia Best TV And Movie Roles To Date

Many first noticed Milo Ventimiglia when he got the role of Jess Mariano, Luke's rebellious nephew who blows into Stars Hollow and steals Rory's heart on the WB hit "Gilmore Girls." Those who missed Ventimiglia's turn as a brooding teen discovered him in his lead role on NBC's hit science fiction series "Heroes" as Peter Petrelli. Later, others came to love him as Jack Pearson in NBC's family drama "This Is Us." Ventimiglia has starred in his fair share of popular network TV shows, but he has also done shorter-run series, guest appearances, and films that are worth checking out.

Ventimiglia has been attached to a variety of projects, giving him the opportunity to play many different types of characters. From a brooding teenage bad-boy to an undercover officer, even Ventimiglia's early work shows range, and a desire not to be pigeonholed into a specific archetype. Ventimiglia's adult roles have also been varied, as he plays everything from a superhero to a serial killer. Join us as we explore Milo Ventimiglia's best film and television roles.

Opposite Sex (2000)

In his first lead role, Ventimiglia was cast as Jed Perry in the one-season run of Fox's "Opposite Sex." When 15-year-old Jed moves to Northern California looking for a fresh start after his mother's death, he has a rough go of it. His new school, Evergreen Academy, was until very recently only open to girls. He arrives during the first year that boys are allowed, and there are only three male students in the entire sophomore class. 

Before Jed moves away to attend Evergreen Academy, his girlfriend breaks up with him, leading Jed to swear off women. Finding himself surrounded by girls after this vow is fodder for much of the comedy in the show. Because of its short run, we don't get to explore the world of  "Opposite Sex," but Ventimiglia's comedic timing is on point, and the absurdity he experiences creates some humorous moments. Although this series only lasted one short season, it features some actors who went on to become big stars, including a young Chris Evans.

Boston Public (2003)

In 2003, Milo Ventimiglia was cast as an undercover officer in Fox's "Boston Public." Ventimiglia plays Jack Provesserio in a four-episode story arc. Upon infiltrating the high school as a student, he clashes with a young and idealistic teacher over his developing friendship with her student, the sister of a young man who has been dealing drugs. Jack wants to meet with the supplier operating above the low-level dealers so that he can arrest him for selling drugs to students. 

Although this wasn't a starring role for Ventimiglia, it was an opportunity to play an adult role during a time that he was still predominantly being cast as a teenager (despite being in his 20s). It was also a serious role, allowing him to prove that he could do both drama and comedy. Ventimiglia's role as Jack Provesserio ends when his character is killed in the line of duty, protecting students during a drug bust gone wrong.

American Dreams (2004–2005)

Milo Ventimiglia joined the cast of NBC's "American Dreams" for the last season as Chris Pierce, the new kid at school who starts dating Brittany Snow's character, Meg Pryor. A period drama set in 1960s Philadelphia, "American Dreams" revolves around a group of teenagers and their families as they grapple with the cultural changes sweeping America. Meg Pryor is the main character of the show and part of a conservative Catholic family, which is frequently in conflict with the counterculture movements growing in popularity amongst the youth of the country.

She is a dancer on "American Bandstand," hosted by Dick Clark (who is actually a producer on "American Dreams"). Meg's traditional upbringing is challenged when her brother goes off to fight in Vietnam, and when Ventimiglia's character Chris Pierce comes into her life. Chris is a rebellious teen who wants to be involved in the anti-war effort, challenging Meg's worldview and often leading to family tensions. Ventimiglia knocks it out of the park as a young activist.

Gilmore Girls (2001–2006)

Milo Ventimiglia got his major break when he landed the role of Jess Mariano on the WB hit "Gilmore Girls." Jess comes to live with his uncle Luke (Scott Patterson), striking up a friendship with Rory and destabilizing her relationship with the sweet but dull Dean (Jared Padalecki). Although Jess is a rebellious underachiever, he is smart and well-read, both qualities that immediately draw Rory to him. He was on the show for 39 episodes, most of which saw him featured as a series regular while Rory and Jess are dating. Ventimiglia reprised this role in Netflix's "Gilmore Girls: A Year in the Life" in 2016.

Ventimiglia seems to have come to terms with things not working out between Rory and Jess in the long run. As reported by Entertainment Weekly, Ventimiglia spoke with Scott Patterson on his podcast, saying, "Jess and Rory, I think they were what they needed at the moment from each other. At the same time, you know, it didn't work out. They went in different directions, and that's okay too. That's kind of great." When Patterson asked if Ventimiglia would be willing to reprise the role of Jess again he said, "I think if they did want to bring it back, and if it was Amy and Dan at the helm, and you guys were all showing up, I'd be a jerk not to show up."

The Bedford Diaries (2006)

In 2006, Milo Ventimiglia played Richard Thorne III in the miniseries, "The Bedford Diaries." This series explores the lives of students in a controversial human sexuality class at a fictitious university in New York City, all of whom come from different walks of life with wildly varying backgrounds. While many of the students are privileged financially, some are commuter students who live in other areas of New York, making their experience at school different than their wealthier classmates.

Richard is the new editor of the student newspaper, and he is pursuing a story about a married professor who had an affair with a student the prior year. He is also a reformed alcoholic who is trying to take life and school more seriously, but he still speaks with fluent sarcasm. Ventimiglia's character is the most compelling of the group of students, but Matthew Modine as Professor Macklin, who teaches the human sexuality class, is also an underappreciated gem on "The Bedford Diaries."

Rocky Balboa (2006)

2006 was a big year for Milo Ventimiglia. He had two shows on network television, as well as a prominent role in a major theatrical release. Ventimiglia plays Rocky's son, Robert Balboa Jr., in "Rocky Balboa." From a physical perspective, the casting is absolutely perfect — Stallone and Ventimiglia even have the same crooked grin, because both actors, interesting enough, have similar facial nerve damage.

In this film, Rocky has been retired for years. He now runs a restaurant and is grieving the death of his wife Adrian, when an exhibition boxing match with the current heavyweight titleholder brings Balboa out of retirement. This decision puts a strain on his already complex relationship with his son, Robert, played by Ventimiglia. His role in the film isn't huge, but it has heart and depth to it. Father-son relationships can be complicated, especially when the son feels like he is living in the shadow of his father, as Robert Jr. does.

In 2006 when asked in an interview with Movie Web about a pivotal scene between Rocky and Robert, Ventimiglia said before filming started he discussed the scene with Stallone, "we started discussing Robert's problems and the way he was viewing his life. Sly said to me, 'It's not about how hard you can get hit, it's about how hard you can get hit and keep going forward.' It's funny to see that line at the top of the trailer. It relates so much to what the kid needs to hear ... It serves as a starting point about where this father-son relationship goes."

Heroes (2006-2010)

The role that would finally make Milo Ventimiglia a major television star came after 11 years of acting. In 2006, Ventimiglia was cast as Peter Petrelli, an EMT with superpowers in NBC's science fiction hit show "Heroes." Over the course of four seasons, we explore the world of superheroes and villains in this imaginative series. Ventimiglia's Peter Petrelli is a quintessential hero: he's an honest, hardworking young man from a wealthy family who wants to make his own way in the world. Driven to help people, Petrelli goes into healthcare.

Although the fame of his character is a testament to his acting skills, it also meant it was hard to move on from Peter Petrelli when the series came to its end. In an interview with Access Hollywood, Ventimiglia said that he couldn't get a job for an entire calendar year after "Heroes" reached its conclusion. He actually considered leaving the business, moving to Italy and, living the simple life — but before he took the plunge away from Hollywood, Ventimiglia got a part in a film and continued with his career as an actor.

Chosen (2013)

In 2013, Milo Ventimiglia was cast as Ian Mitchell, a lawyer forced to kill in order to save his family in the Crackle original series "Chosen." In the first episode of the series, Ian Mitchell wakes up to a box at his doorstep. Inside, it contains a gun and a photo of the person he must kill in three days' time, or his kidnapped daughter will be killed. Over the course of this tense, action-packed series, we watch a normal family man transform into a reluctant assassin to protect his family.

Ventimiglia spoke with Daily Actor about his role in the streaming series, heaping praise on both the production and the director, saying, "What attracted me to it was a good character with a great story, you know, something kind of interesting and original and the filmmaker, you know, Ben Ketai. He's an awesome guy. He's a great shooter. He understands story and heart and character."

The Whispers (2015)

In 2015, ABC's "The Whispers" aired for only one chilling season. This mysterious science fiction series is about an invisible entity manipulating children into harming others. Milo Ventimiglia plays a John Doe, found in the African desert, with no knowledge of who he is. He later travels to the U.S., eventually learning that he is Sean Hennigan, a man who went missing on a mission for the U.S. military and was presumed dead. 

In an interview with KSiteTV, Milo said of his character, "He has no memory of who he is ... he has no memory of where he is going. He just has this pull, this sense of direction that he has to follow. Kind of call it an instinct ... to go somewhere. But it's also very much a path of destruction — not by his hand, necessarily — but he's cloaked in darkness." As the show progresses, Ventimiglia's character Sean comes into clearer focus. Unfortunately, the series was canceled after only one season, but it is nevertheless an unsettling and interesting mystery worth checking out.

Gotham (2015)

After having a hard time getting cast for over a year after "Heroes" ended, it seems like Milo Ventimiglia is choosing parts with the goal of no longer being pigeonholed into a specific character type. To that end, he took the role of Jason Lennon (The Ogre), a serial killer, on three episodes of Fox's "Gotham." Although this wasn't a leading role, Ventimiglia was a terrific guest star — he is terrifying on the show. In an interview with Fox 11 Los Angeles, Ventimiglia shared how he tried to get into the character's head, playing Lennon as someone who is looking for love, despite being a serial killer, with a skewed perception of what love is.

In an interview with the Hollywood Reporter, Ventimiglia said, "[It's fun to have] the opportunity to step outside of yourself and create a character that, in real life, we just can't do. I mean, we can, but we'll go to jail." Ventimiglia was a fan of the series, watching it to support his friend Ben McKenzie, who plays Jim Gordon in "Gotham." When asked about taking the role, Ventimiglia said, "The idea of who this guy is, and why he is, is so compelling that every turn, every kill, every moment for this guy — there's a reason why he's doing it all. It may not be your reason or my personal reason, but there is a reason." Jason Lennon's story arc on "Gotham," is twisted, frightening, and pretty awesome.

Creed II (2018)

Several years after the release of "Rocky Balboa," Milo Ventimiglia would reprise his role as Robert Balboa Jr. in "Creed II." The appearance itself is barely more than a cameo, but it is essential to the story. When "Creed" came out, longtime "Rocky" fans wondered where Robert was. Why wasn't he taking care of Rocky while he was sick with cancer? In "Creed II" we get our answer — the father and son are estranged. Although Ventimiglia is only on screen for one scene, where Rocky shows up at Robert's door at the end of the film, we can't help but wonder if Ventimiglia will play Robert Jr. in later installments of the growing "Creed" franchise.

As reported by /Film, Sylvester Stallone has been vocal about "Creed II" being the last time he will play the iconic role of Rocky Balboa. But the new boxing franchise has been successful in having other actors reprise their roles — even Dolph Lundgren returns, coming back to play Ivan Drago in "Creed II." Even if Ventimiglia never plays Robert Balboa Jr. again, it was cathartic to see the father and son come together one last time. For franchise fans, it feels like an appropriate place to leave Rocky's story.

The Art of Racing in the Rain (2019)

In 2019, "The Art of Racing in the Rain" won audiences' hearts. The film is an adaptation of a bestselling book of the same name by Garth Stein. Milo Ventimiglia plays Denny Swift, a race car driver who buys a golden retriever puppy, naming him Enzo, after Enzo Ferrari. The story is told from the perspective of Enzo, voiced by Kevin Costner. Denny is the center of Enzo's universe, and he grows up accompanying Denny to the racetrack. Enzo even wants to be reincarnated as a human in his next life so he can become a race car driver too. Ventimiglia is excellent in his role, and you can't help loving him as much as Enzo does.

But one day Denny meets a girl, falls in love, gets married, and starts a family. While Enzo is initially reluctant, he comes to love Denny's wife and his new human sister. "The Art of Racing in the Rain" is a story about the special bond between a man and his best friend, and the way family pets can be emotional support during our hardest times. It is tender and sad, but oh so sweet.

This is Us (2016-2022)

If you haven't seen "This Is Us," you've been missing out. In 2016, the NBC family drama became an instant hit with viewers. The series explores the Pearson family both in the present day and through flashbacks, as we see the three siblings' childhood and their parents' courtship before the kids were born. Mandy Moore and Milo Ventimiglia star as the parents in this series, with Ventimiglia playing the role of Jack Pearson. The show pulls at your heartstrings when you realize Jack is no longer alive in the present day, and you have to keep watching almost against your will to discover how he dies.

Jack Pearson is a complex but lovable character. When asked what he learned from playing Jack in an interview with E!, Ventimiglia said, "Gosh, Jack's shoes are definitely hard to fill. You know, for as golden as Jack is, he's equally flawed and yet he's still very loved ... Knowing that there's the balance — equal parts of the good and the bad — and always striving to be good, I think that's always been a constant theme of my life. You put the best foot forward and hopefully you're impacting people positively."