Van Winkle made his television debut in a December 2004 episode of the Fox sitcom Quintuplets, and has since appeared in shows such as That's So Raven, Malcolm in the Middle, The O.C., and 7th Heaven. His film credits include one of the leads in Fox's Meet the Spartans, David R. Ellis's film "Asylum", Universal's Accepted and Michael Bay's Transformers. While he has modeled for Abercrombie & Fitch shot by Bruce Weber, Van Winkle appeared in New Line/Paramount's 2009 reboot of Friday the 13th as Trent DeMarco, the character he previously portrayed in Transformers. In an interview with Fearnet, Van Winkle said that he was very hyped about the film, and enjoyed playing in it. He also appeared in Julianne Hough's 2008 music video for "That Song in My Head". In 2011, Van Winkle starred in the suspense thriller film247°F co-starring Scout Taylor-Compton. In 2012, he starred in the independent comedy Last Call about two underachieving cousins, Danny and Phil have to prove themselves when they are charged with managing the family pub, in a bid to save their wayward uncle from prison and financial ruin. He starred as Greg in the thriller Bloodwork co-starring Tricia Helfer. In 2011 and 2012, Van Winkle made guest appearances in television series such as Happy Endings, 2 Broke Girls, and Two and a Half Men. In October 2012, he was cast as Lieutenant Daniel Joshua "Danny" Green, leader of the Naval Mountain WarfareSpecial Forces Unit aboard the Nathan James, in the TNT action drama pilot The Last Ship, also executively produced by Bay. The series premiered on TNT on 22 June 2014. In December 2012, he was cast in a recurring role as Jonah on the second season of The CW's series Hart of Dixie. In 2014, Van Winkle starred as Coke in the comedy filmMantervention. Van Winkle guest starred in an episode of Scorpion, where he played Ensign Nathan Hall, who gets trapped with Walter, Happy and Cabe in a downed submarine and must figure out how to escape before they run out of air. In 2015, he starred in the PixL original movie Bound & Babysitting alongside Tammin Sursok. In 2017, Van Winkle starred as Scott Hays in Hallmark channel original movie Christmas Getaway alongside Bridget Regan.
