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He signed on for a spin-off of Gilmore Girls called Windward Circle which was to be focused on the relationship between Jess and his estranged father (played by Rob Estes), but the proposed series never made it to air.Afterward, he dropped down to a guest star/recurring cast member, and he came back for four episodes in season four and two episodes in season six.The comic is about John Barrett, a white-collar New Yorker whose life changes when he becomes addicted to a drug that prevents him from falling asleep.Divide also has a comic book called Berserker written by Rick Loverd.The same year, he was cast as Robert "Rocky Jr." Balboa, the son of Rocky Balboa, in the sixth Rocky installment Rocky Balboa which was released in December 2006.

In between television work, Ventimiglia had supporting roles in the horror films Cursed (2005), directed by Wes Craven, and Stay Alive (2006), as well as starring roles in the short-film Intelligence and the full-length feature Dirty Deeds (2005).He starred as Peter Petrelli on NBC's Heroes from 2006 to 2010, for which he received nominations for Teen Choice, Saturn and People's Choice Awards.He also had roles in the horror films Pathology (2008) and Kiss of the Damned (2013).Ventimiglia also produced and developed a mini web-series called It's a Mall World as part of a marketing campaign for American Eagle Outfitters in 2007.In mid-2007 he starred as the love interest of pop/R&B singer Fergie in the music video for "Big Girls Don't Cry".

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