Though Jason Gedrick is primarily a supporting actor, his first role was relatively impressive for a newbie; in 1983, he appeared as an extra in the cast of Bad Boys with Sean Penn, who encouraged Gedrick, then a Chicago high-school student, to further pursue acting. Penn's advice paid off fairly quickly, considering that by 1985, Gedrick had landed leading roles in Iron Eagle, The Zoo Gang, and The Heavenly Kid. In 1988, Gedrick starred as a washed-out basketball player-turned-police officer opposite Meg Ryan and Kiefer Sutherland in Promised Land, and went on to play small roles in Born on the Fourth of July and Backdraft. Between film roles, Gedrick kept busy with stage work, starring with Helen Hunt and Don Ameche in a Broadway production of Our Town, as well as an off-Broadway production of Mrs. Dally Has a Lover with Judith Ivey.
Though Gedrick was less successful on the big screen during the mid-'90s, the actor was praised for his television work. In 1996 and 1997, Gedrick starred as a murder defendant in Steven Bochco's Murder One, and later starred opposite Ken Olin and Joe Pantoliano in CBS's critically acclaimed series EZ Streets. Gedrick was also recognized for his work with Danny Aiello and Joe Mantegna in The Last Don and The Last Don II, both six-hour CBS miniseries. Gedrick enjoyed similar success for his lead role in the CBS drama Falcone, which was based on the feature film Donnie Brasco, and would go on to land a lead role alongside Billy Baldwin and Chazz Palminteri in One Eyded King (2002). Gedrick could also be seen in NBC's Boomtown (2002) and the made-for-cable drama A Date With Darkness: The Trial and Capture of Andrew Luster.
In 2006 he joined the cast of NBC's television series Windfall, which co-starred his former Boomtown alumni Lana Parilla. Though Windfall was short-lived, he would return to television for the A&E original movie Kings of South Beach (2007), in which he worked alongside Donnie Wahlberg. Gedrick appeared on seasons 3 and 4 of Desperate Housewives to play the love interest du jour, and joined the cast of HBO's drama Luck in 2012.