Gilford was born in Evanston, Illinois, the son of Anne and Steve Gilford. His mother is Lutheran, and his father is Jewish. He graduated from Evanston Township High School and Northwestern University. He worked as a trip leader for Adventures Cross-Country and has led wilderness and adventure trips for teenagers to Alaska, British Columbia, California, Hawaii, and the South Pacific. Gilford also worked as a staff member for YMCA Camp Echo in Fremont, Michigan.[citation needed]
In 2005, he appeared in an episode of Law & Order: Special Victims Unit. In 2006, Gilford landed a regular role in Friday Night Lights, in which he played the role of Matt Saracen in the main cast, from Season 1 to Season 3. In 2009, Gilford was switched to the recurring cast in Seasons 4 and 5. That year, he also made his feature film debut, co-starring in The Last Winter (2006). He had a cameo in the film Rise: Blood Hunter and guest starred in an episode of Grey's Anatomy.
In 2009, he co-starred as Adam Davies in the romantic comedy Post Grad opposite Alexis Bledel. He also starred as Johnny Drake in the romantic drama Dare opposite Emmy Rossum. In 2010, he starred as Gus in the indie drama film The River Why alongside Amber Heard. He had a cameo in the movie Super.

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