The Quiet Art of Being a Sideman

By Katie Ogletree | Photography by Jim Clark

There is a particular kind of musician who can spend a lifetime standing beside the spotlight without ever being diminished by it. In jazz, these musicians are called sidemen. The word can sound secondary, but anyone who has spent time listening closely to great jazz knows better. The right bassist can transform a soloist. The right drummer can change the emotional temperature of an entire performance. A great rhythm section doesn’t just accompany the music; it creates the environment in which the music becomes possible.

Steve Gilmore has spent nearly seven decades mastering that art. Now, let’s be clear: they don’t just hand out the name “sideman” to anyone. To even be considered one, you have to know how to play every single song in the Great American Songbook in every key, at any reasonable tempo, with people you’ve never met, without sheet music. That is no small feat.

Steve was born in Trenton, New Jersey, in 1943 and began playing bass at the age of twelve. By fourteen, he was already performing professionally. Growing up within reach of Philadelphia’s jazz scene, he absorbed live performances by musicians including John Coltrane, Max Roach, Sonny Rollins, and Wynton Kelly.

His musical education eventually took him to Toronto’s Advanced School of Contemporary Music, where he studied with one of the giants of the instrument, bassist Ray Brown. From there, Gilmore developed his career the old-fashioned way: by playing, listening, traveling, and working.

He worked with musicians such as Ira Sullivan, Flip Phillips, Al Cohn, Zoot Sims, and Mose Allison. He also became part of a remarkably durable rhythm partnership with drummer Bill Goodwin. That relationship would become central to one of the defining chapters of his career: in 1974, Gilmore and Goodwin joined the newly formed Phil Woods Quartet; in 1977, under The Phil Woods Six, they won the Grammy for Best Jazz Performance by a Group for “Live” from the Showboat; in 1982, they won for Best Instrumental Jazz Performance, Group for More Live — The Phil Woods Quartet; and in 1983, the group won Best Instrumental Jazz Performance, Group for At the Village Vanguard — The Phil Woods Quartet.

The Phil Woods organization itself describes Gilmore and Goodwin as original members who remained with the group for more than thirty-five years. The longevity alone is remarkable. Jazz musicians traditionally move from group to group, but the two became the rhythmic foundation of Woods’ ensemble through years of changing personnel.

Gilmore’s résumé reads almost like a map of American jazz. Over his career, he has worked with figures including Dizzy Gillespie, Chet Baker, Art Blakey, Philly Joe Jones, Sonny Stitt, and Freddie Hubbard, while also crossing into the worlds of Tony Bennett, Tom Waits, Bernadette Peters, Rosemary Clooney, Les Paul, and Dave Matthews.

The new nonprofit documentary film Sideman: The Legacy of Steve Gilmore finally puts the spotlight on the musician who spent his career making sure the spotlight fell on everyone else. Produced and directed by Emmy-recognized documentarian Dave King in partnership with the SOWAL Foundation, Sideman combines archival material, new interviews, studio sessions, and a live performance to tell the story of Gilmore’s extraordinary career. The project also includes a companion soundtrack intended to preserve and extend his musical legacy.

“Somewhere along the way, I realized it needed the sound of Steve himself—still playing, still listening, still holding the room together the way great bass players do,” says King. “That is how this album began.”

Steve Gilmore, Bill Charlap, Dennis Mackrel, and Jon Gordon walked into Sear Sound studio back in March 2026 as four master musicians with separate histories, languages, and lives in music. They had not spent years touring together or rehearsed this album to form a comfortable rhythm together. They came together in New York City’s oldest recording studio and trusted the thing that great sidemen know better than almost anyone: how to listen.

Bob Green, producer/director Dave King, and Steve Gilmore

Bill Charlap is widely regarded as one of the great living interpreters of the American Songbook, a pianist with the rare ability to make familiar songs feel newly discovered. Dennis Mackrel was Count Basie’s final drummer, later entrusted with leading one of the world’s most celebrated jazz orchestras. Jon Gordon received the Thelonious Monk Award for alto saxophone, one of the highest honors a jazz musician can earn. And Steve Gilmore brought the authority of a lifetime spent making other people sound legendary.

Contrary to popular assumptions, sidemen are not supporting characters. They are the quiet architects of jazz, and this album is proof. According to King, the recording sessions are intended not only to document Gilmore’s playing but to create a career-defining album for another generation to experience.

The filmmakers explicitly position the film within that larger goal as they prepare to premiere it this fall. Sideman focuses on what it means to continue working as a professional musician late in life and on the peers who helped create the soundtrack of the last seven decades. The greatest lesson in Steve Gilmore’s story may be that sometimes the most important person in the room is not the one standing in the spotlight. And for Steve specifically, he is never really in the background. He is the foundation of each great performance.

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Check out Sideman: The Legacy of Steve Gilmore, coming soon from producer/director Dave King and the SOWAL Foundation. Visit SidemanTheFilm.com to learn more.