After living in Minneapolis to manage a friend's band and do freelance music writing, DeRogatis first joined the "Chicago Sun-Times" in 1992; he left in 1995 to join "Rolling Stone" magazine, a job that lasted eight months, and was back at the "Sun-Times" in three years. While at "Rolling Stone" magazine, he was fired after writing a negative review of Hootie & the Blowfish's album "Fairweather Johnson". The review irked "Rolling Stone" publisher Jann Wenner who had it pulled from publication. DeRogatis's employment with the magazine was terminated after he revealed this incident to the public.