Actor Chris Elwood first appeared on TV as a guest star on the series In the Heat of the Night in 1994 but was ultimately recognized as one of Ashton Kutcher's wingmen on the MTV prank show Punk'd in 2004. Three years later, he joined the cast of the reality series Flipping Out, which focuses on the day-to-day adventures of real estate investor Jeff Lewis.
In the first season of Flipping Out, Elwood was referred to as the "Trash Guy" and by the second season, he became the "House Manager." He was eventually fired by Lewis for not doing his job well, which caused tension in his marriage with Jenni Pulos, who also appeared on the show as Lewis' assistant.