1995

Milo Ventimiglia

October 09

Milo's Fresh TV Debut

Ventimiglia, who studied theatre at UCLA and San Francisco's American Conservatory, lands his first paying acting role on The Fresh Prince of Bel-Air. In 1996, he stars as a gay man in the short, Must be the Music, which opens to rave reviews at the 1996 Sundance Film Festival.

2000

Milo Ventimiglia

July 17

Milo's Many Failed Series

After a series of failed TV shows (CBS' Brooklyn South and the Touched By An Angel spin-off Promised Land), Ventimiglia headlines the highly touted Fox series Opposite Sex. In this teen angst dramedy, he plays one of three boys entering an all-female institution. "I'm thinking about the future," the actor, 23, tells Tennessee's News-Sentinel. "If this show is a hit, then that's great. If it isn't, it has been a learning experience." The show turns out to be a learning experience.

2001

Milo Ventimiglia

October 30

Rory Gilmore's Jess

Ventimiglia plays the intelligent rebel Jess Mariano on the WB's Gilmore Girls with Alexis Bledel (left). After two seasons, he is set to carry his character into a highly anticipated spin-off. But it doesn't come together. Creator Amy Sherman-Palladino, who compares the actor to Johnny Depp and Jake Gyllenhaal says, "The door is always open for his return."

2002

Milo Ventimiglia

Taking it Offscreen

Ventimiglia and costar Alexis Bledel (right) keep their off-screen relationship low profile. In 2006, Bledel admits to PEOPLE that they have discussed marriage: "I think everybody who has been dating for more than a couple of years probably talks about it at some point." In July 2006, after three and a half years together, Bledel and Ventimiglia announce their breakup. "There's an emotion that goes with that," he tells Men's Fitness in 2007. "I didn't really keep myself together as I should have."

2004

Milo Ventimiglia

October 03

American Dreams

Ventimiglia, 27, plays Chris Pierce, an anti-war activist and Brittany Snow's (left) onscreen boyfriend, on NBC's 1960-era drama American Dreams. The role hits close to home. "My dad did two tours in Vietnam," Ventimiglia tells Tennessee's News-Sentinel. "This is a landmark character for me because it does tie into my father."

2006

Milo Ventimiglia

September 25

A Heroic Return

After starring in the failed WB series The Bedford Diaries with Gossip Girl star Penn Badgley, Ventimiglia plays Peter Petrelli on NBC's new sci-fi series, Heroes. "When I first read the script, I was like, 'Wow, that's great, [Peter] can fly!' But he can't," Ventimiglia tells the New York Post. "Instead, Peter feels other people's emotions and makes them aware of what they're capable of. What that turns into is very interesting, but I don't want to spoil it – people will find out pretty quick what that really means."

Milo Ventimiglia

December 20

Playing Rocky's Boy

Ventimiglia, 29, plays Sylvester Stallone's son in the latest Rocky installment, Rocky Balboa. "I thought if Rocky and Adrian had a child, (Milo) would be a perfect offspring. He sort of resembles her and (looks like) he'd be intimidated by Rocky," Stallone (left) tells USA Today. The movie eventually grosses more than $70 million at the box office. "(Stallone) wrote the film, he directed it, he starred in it," Ventimiglia tells Men's Fitness. "If I could do that, do it all – producing, directing, acting – I'd love it." Ventimiglia devotes his time to Divide Pictures, the three-year-old production company he co-founded, which will produce shorts for American Eagle and other film and TV projects.

2007

Milo Ventimiglia

May 11

Unexpected Success

In its first season Heroes pulls in more than 14 million viewers weekly, and Entertainment Weekly puts Ventimiglia on one of five covers dedicated to the show's frenzy. The special edition reflects the success of TV's top-rated new series, which makes household names of formerly unknown stars like Ventimiglia, Ali Larter and Hayden Panettiere. "When we were doing the photo shoot for this story," costar Adrian Pasdar tells EW, "we were all looking at each other like we were our own stand-ins. We kept waiting for the real stars to show up."

Milo Ventimiglia

May

Milo, the Lover Boy

Ventimiglia plays Fergie's love interest in her hit video, "Big Girls Don't Cry" (left). His performance as the pop star's "shirtless, chiseled man-pillow" ranks him at No. 12 on EW.com's Sexiest Video Guest-Stars of All Time.

2008

Milo Ventimiglia

January 06

'Halo': A Heroic Pairing

Although he plays her uncle onscreen, Ventimiglia, 30, is spotted holding hands with costar Hayden Panettiere, 18, at an L.A. mall. The PDA confirmation of their relationship comes after months of denials from both stars. "When you're in the public eye, you try to keep whatever you can private," he tells GQ. In February 2009, the couple calls it quits.

Photo Credits

BIOGRAPHY (top to bottom): amazon.com; Sara De Boer/Retna; Everett Collection; JPI

Edited by Julia Wang

Milo Ventimiglia

Celebrity Central / Top 25 Celebs

 

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