He received his first national exposure for his daily roundup of the O.J. Simpson trial. After that, he continued to host his regular show on WLS (AM). Eventually he teamed up with Garry Meier to cohost the highly successful Roe & Garry Show. In 2004, amid an impasse in contract negotiations with the station, Meier did not renew his contract with WLS. Roe then became the sole host of the show, which also featured Jim Johnson and Christina Filiaggi. Many praise Roe Conn for having a good sense of humor and for being skilled at articulating his thoughts. In the spring 2006 ratings period, The Roe Conn Show became Chicago's most listened-to radio talk show among adults.