In 1998, Skinner began co-hosting a progressive weekend radio show called "Ski & Skinner" on WLS in Chicago where she was fired after announcing, on air, that she was running for the U.S. Senate. In 2000, Skinner became co-host of The Doug Stephan Show, a syndicated national morning show heard on over 400 radio stations across the United States. Skinner's show inspired two listeners, Anita and Sheldon Drobny, to create the Air America Radio Network featuring Al Franken and other liberal radio hosts.