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We’re big fans of hot, brooding dreamboat Milo Ventimiglia. Here are 16 of his best roles in his career so far, lovingly ranked for your enjoyment.

Jess Mariano forever: An official ranking of Milo Ventimiglia’s greatest roles

Do you like dogs, fast cars, and hot, brooding dreamboats? We do, too! Hot, brooding dreamboat Milo Ventimiglia has been cast opposite luminous Hollywood goddess Amanda Seyfried (Les Misérables) in the upcoming adaptation of Garth Stein’s The Art of Racing in the Rain.

The 2008 novel was told from the perspective of a family dog who evaluates his life through the lessons learned by his owner Denny (Ventimiglia) – a dishy race-car driver with biceps for days. (We may have elaborated on that last part).

We’re big fans of the eminently appealing actor here at Film Daily and have some thoughts about how eclectic and entertaining Ventimiglia’s career has been. Here are 16 of Ventimiglia’s best roles in his career so far, lovingly ranked for your enjoyment.

16. Letterman: Sabrina the Teenage Witch (1996)

Such a minor, brief role that his character doesn’t even have a name. Nonetheless, we’re eternally charmed by the fact Ventimiglia starred as a jock in one of the greatest cult teen shows of all time.

15. Josh: The Divide (2011)

Ending what we’ll go ahead and call the “bad boy” era of Ventimiglia, the actor portrayed a despicable monster losing his grip on ethics and morality in the bunker of an apartment building at the end of the world. It’s a bleak, nasty tale and so is Ventimiglia’s depiction of the character.

14. Frat Boy Milo: Grown Ups 2 (2013)

Look, there’s nothing noble about this role. But there is something exceptional about seeing Ventimiglia sport a bleach blonde frat-flop and perform drawn out, elaborate high fives with Taylor Lautner (Twilight). He’s a total bro and we love him.  

13. Rick Rape: Gamer (2009)

Of course a movie from the deranged minds of Mark Neveldine and Brian Taylor (Crank) happens to also feature the weirdest performance from Ventimiglia on this list. As a horny avatar in a slick PVC ensemble, Ventimiglia delivers strained laughter and creepy come-ons while humping against the leg of Angie (Amber Valletta) like a rabid puppy. The whole thing is as grotesque as you’d expect from the directors (and frankly a shock to see Ventimiglia depict!).

12. Jackson Pritchard: Devil’s Gate (2017)

Clay Staub’s atmospheric creature feature sees Ventimiglia sporting a rough dusting of facial hair and a set of tremendous snarling facial expressions. Works for us!

11. Ted Grey: Pathology (2008)

Though Marc Schölermann’s medical thriller isn’t perfect by any means, Ventimiglia delivers a captivating performance as a student who unwittingly becomes part of a gruesome, macabre game.

10. Chad: That’s My Boy (2012)

The less said about Adam Sandler’s infantile comedy about a kid who impregnates a teacher, the better. However, we do have a soft spot for Ventimiglia’s stern portrayal of a soldier home for his sister’s wedding and about ready to kill her hapless, soon-to-be groom (Andy Samberg).

9. Jed Perry: Opposite Sex (2000)

Starring as one of only three boys who start attending an all girls high school, Ventimiglia was sharp and delightful in this short lived (but surprisingly entertaining) teen comedy show opposite a young Chris Evans (The Avengers).

8. Danny DeMarco: Wild Card (2015)

Playing a despicable rapist about to suffer some distinctly unpleasant revenge courtesy of the woman he attacked (Dominik García-Lorido) and a pissed off bodyguard (Jason Statham), Ventimiglia pushes his pathetic character to perfectly deplorable and often hilarious limits.

7. Paolo: Kiss of the Damned (2012)

Vampire stories are always sexy, right? Damn straight! As you might expect, the combination of Ventimiglia and vampirism makes for a thirsty viewing experience.

6. Peter Petrelli: Heroes (2006 – 2010)

The beloved genre show gave the actor one of his most iconic roles as an ordinary dude with the challenging ability to absorb and demonstrate other people’s superpowers.

5. Jason Lennon / The Ogre: Gotham (2015)

As the Don Juan killer in Gotham, Ventimiglia remains one of the show’s most interesting and ferocious villains to date. As alluring as he is unhinged, the actor is absolutely thrilling in the role as the city’s most hideous serial killer.

4. Rocky Balboa Jr.: Rocky Balboa (2006)

With his jagged accent and proclivity for speaking out of the one side of his mouth, the actor was the absolute perfect choice to play the disappointing son of iconic boxing character Rocky Balboa (Sylvester Stallone). Ventimiglia keeps up with Stallone’s staggering energy in the movie, showcasing hidden depths of anger while maintaining the look of a kid who hasn’t yet figured out how to grow up.

3. Denny Briggs: Madtown (2016)

Charles Moore’s underrated action drama film features one of the best performances of Ventimiglia’s career. While his depiction of a man haunted by family troubles and a singular, harrowing crime hits the soulful beats of his more recent work, it also spotlights the actor’s capability for subtlety and quiet intensity.

2. Jack Pearson: This is Us (2016 – 2018)

TV’s best dad is also one of the hottest. Ever. We could go on forever about how Jack’s casual wardrobe does a great job of showing off Ventimiglia’s impressive biceps, but we’ll keep this professional. The guy delivers a consistently emotional performance in just about every episode of NBC’s family tearjerker, leaving us with a perpetual lump in our throats (and a throbbing in our hearts).  

1. Jess Mariano: Gilmore Girls (2001 – 2006)

Real talk: we will never get over Stars Hollow’s resident brooding, book-loving punk. Jess Mariano was a total jerk for the majority of Gilmore Girls but he still absolutely stole our hearts (and that of Alexis Bledel’s Rory Gilmore).

Ventimiglia was impassioned and irresistible in the role but he also showed off some sterling comedic skills. If there were a way we could just sit and watch this character read the entire works of Allen Ginsberg, we would and it would be just about the dreamiest thing ever.

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