Winstead made her standup comedy debut in 1983 in Minneapolis at the Brave New Workshop. She was a national headlining comedian appearing on shows like HBO's Women of the Night and the Aspen Comedy Festival. She wrote and performed for early Comedy Central shows like Women Aloud, and produced the syndicated talk series The Jon Stewart Show, starring the future Daily Show host. She also created Court TV's Snap Judgment and served as the consulting producer on the pilot of The Man Show. During her time at The Daily Show she helped staff the program with signature talents like Stephen Colbert, Beth Littleford, Brian Unger, and Lewis Black. Winstead has appeared on various shows on CNN and MSNBC as well as a panelist on shows such as Politically Incorrect, Tough Crowd with Colin Quinn and the public-access television cable TV/PBS program Mental Engineering (where she was notably featured in an episode that aired following Super Bowl XXXVI in 2002). In 2002, she and Brian Unger created, wrote and co-hosted O2Be, a satire of network morning programs that was broadcast on the Oxygen network. In 2003, she co-founded and served as the program director at Air America Radio. Until March 2005, she was also co-host of Unfiltered on Air America Radio, along with Rachel Maddow and Chuck D. Since May 2005 she has been a contributing blogger at The Huffington Post.