From March to July 2005, Gayheart starred in a Broadway production of "Steel Magnolias". David Rooney of "Variety" praised her performance, writing: "Exuding all the breezy confidence of a girl who's always been popular and pretty, Gayheart's Shelby provides a strong center, allowing only brief glimpses of the cracks in her cheerful, optimistic veneer and refusing to be treated as fragile goods by the clucking women around her." She also appeared in a minor role in the Christmas horror-comedy film "Santa's Slay" (2005). In 2007, Gayheart guest-starred on "Ugly Betty" as Jordan, an ex-girlfriend of Alexis Meade. The following year, she returned to Broadway in a revival of the comedy, "Boeing-Boeing" opposite Christine Baranski, Mark Rylance, Greg Germann, Paige Davis, and Missi Pyle. She had a guest role on "The Cleaner" in 2009.