Bernie and Rita Jacobs began what could be claimed as the first alternative radio station in America. In the conservative 1950s, at the height of the Joseph McCarthy hysteria, WFMT played not only classical music, but political discussion, theater, and folk music. Mike Nichols and Norm Pellegrini formed the nucleus of station personnel.

Mike decided to host a folk music program on Saturday evenings in 1953. The station signed off early in those days, so the folk program, which began around 11 PM, extended the broadcast day. Yes, The Midnight Special never began at midnight. Mike invited local folk musicians including Fleming Brown and Big Bill Broonzy to jam in the studio that once was the ballroom of an old hotel on the west side of Chicago. Mike Nichols decided to move on to New York, relinquishing the chance to be a nationally famous folk show host. Norm Pellegrini became the host of The Midnight Special as it evolved into a record program, as well as becoming WFMT's program director. Ray Nordstrand, an economics Ph.D. candidate at Northwestern University and a former part-time radio announcer at an Evanston station joined WFMT as an announcer and advertising salesperson, and ultimately served as general manager. Norm invited Ray to share the hosting responsibilities of The Midnight Special. Thus it was for the next 30 years. Various celebrities guest-hosted the program over the years, including Tom Paxton, and theater director Robert Falls.

Although station ownership changed twice, The Midnight Special persevered in its Saturday night time slot. In 1974, Ray Nordstrand hired Rich Warren to assist him with The Midnight Special, as well as to work on general production chores at WFMT. Rich understudied Ray and was invited by Norm to guest host the program in 1983. He quickly became a regular host, alternating with Norm and Ray. He became the program's sole host in 1996 and continues the program's legacy.