He did interviews with such luminaries as Hank Williams, Elvis Presley, and Fats Domino. Gleason was one of the first critics to perceive the importance of Lenny Bruce, Bob Dylan, and Miles Davis.
Gleason was both an observer and a contributor to what is sometimes termed the San Francisco Renaissance, the era of increased cultural vitality in that city which began in the mid-1950s and fully bloomed in the mid-to-late 1960s. In the later 1960s, Gleason was a widely respected commentator and he chose to write supportively of the better cut of the Bay Area rock bands, such as Jefferson Airplane and the Grateful Dead.
With Jann Wenner, Gleason founded the bi-weekly music magazine, Rolling Stone, to which he contributed until his death in 1975.
For ten years, he also wrote syndicated weekly columns on jazz and pop music, which ran in the New York Post and many other papers throughout the US and Europe. For twelve years, he was an associate editor and critic for the leading jazz publication, Down Beat.
For National Educational Television (now known as PBS), Gleason produced a series of twenty-eight programs on jazz and blues, Jazz Casual,
featuring B.B. King, John Coltrane, Dave Brubeck, the Modern Jazz Quartet, Jimmy Witherspoon, and Sonny Rollins, among others. The series ran from 1961 to 1968. He also produced a two-hour documentary on Duke Ellington, which was twice nominated for an Emmy.
Gleason's lasting legacy however, would still be his work with Rolling Stone. His name, alongside the late Dr. Hunter S. Thompson still remains on the magazine's masthead today, more than three decades after his death as testimony to his legacy.