Crawford made his film debut in the 2006 supernatural horror-thriller The Covenant, as Tyler Simms. In March 2007, he landed the role of main character Nate Archibald on The CW's teen drama series Gossip Girl, making his television debut. In 2008, Crawford co-starred in the crime-thriller Loaded, and portrayed the lead role in the supernatural horror film The Haunting of Molly Hartley. The following year, he played English singer-songwriter Leona Lewis' boyfriend in the video for her single "I Will Be", which was released in January 2009. That same year, Crawford was named "Summer's Hottest Bachelor" by People.