Growing up, Jeremy says he tried to be "just like his brother". Jeremy was a model for Abercrombie & Fitch and starred in the Disney Channel original movie The Cheetah Girls 1. In 2005 he had a role on Dawson's Creek playing Dawson Leery's best friend Joel Davidson.
He played an actor/model named Jeremy Hamilton in 2006 on the television series Gilmore Girls. In 2006 he was seen in the horror film Hostel, which grossed $29 million worldwide. In 2007, he appeared in the romantic comedy film The Painted Veil with Naomi Watts and Edward Norton.