He worked as an acting instructor at Sacred Heart University, where he led a children's theater class. After his first commercial film, Galaxy Quest, came out, people noticed he looked a lot like his co-star Tim Allen.
He played a major role in the science fiction comedy film Idiocracy.
His mother Wendy is a former actress. He had an on-and-off relationship with actress Drew Barrymore between 2007 and 2010. He then dated Amanda Seyfried from 2013 to 2015. In 2016, he began dating musician Lauren Mayberry; the couple broke up in 2018. He and Kate Bosworth started dating in 2022.