Chelsey made her TV debut on Scare Tactics (2004) and her first leading role in a film was in Dr. Chopper (2005). She went on to guest star in The Office, CSI: Miami, Journeyman, Better off Ted, Happy Endings, Rizzoli & Isles, Mike & Molly, and New Girl, among others. Crisp also starred as Chloe, one of the contestants on the mock reality game show, The Joe Schmo Show.