Charles Owens grew up in Alexandria, Virginia, across the river from Washington, D.C., and moved to New York in 1992 to enter the jazz program at the New School. His timing was almost absurdly good. Smalls, the basement room on West 10th Street that Mitchell Borden opened in 1994, was about four months old when Owens introduced himself to Borden and asked for work. He got a gig a few weeks later, then took over the club's Sunday afternoon jam session, which the New School sponsored. He was 22.

What followed was one of the longer club residencies of the 1990s New York scene. Owens graduated from the Sunday jam to the Friday late-night slot, which at Smalls meant a downbeat around 2:30 on Saturday morning, and he held it for eight years. For seven months in the mid-1990s he lived in the club, working the door in exchange for a place to sleep and unlimited practice time. "It was my home, literally, for a while," he said later of that period. "The only thing I had to do was work the door and then play gigs and practice. That was my entire existence, you know. I had no cell phone. I had no computer."

His recorded trail from those years runs through other people's records first. Impulse! documented the club on Jazz Underground: Live at Smalls in 1998, and the Charles Owens Quartet got two of the album's nine tracks, "Scenic Roots" and "Losing Victory," alongside sets by the Omer Avital Group, the Jason Lindner Big Band, and the Frank Hewitt Sextet. A year later Fresh Sound New Talent issued Eternal Balance, Owens's first album under his own name, with Lindner on piano, Avital on bass, and Daniel Freedman on drums. That same circle is why Avital's catalog keeps circling back to Owens: he is one of the three tenor players on Avital's piano-less Smalls quartet tape of April 18, 1996, released nine years later as Asking No Permission, and he returns on Room To Grow, recorded live at Smalls in early 1997 and held back until 2007. He also played tenor on Lindner's Premonition (Stretch Records, 2000).

By 2003 Smalls was on the verge of closing, and Owens, facing the loss of the room his musical life had been built around, started taping his own Friday sets on the CD-R deck behind the bar, fed by two condenser microphones hanging over the crowd. Those recordings sat for two decades before he began issuing them as The Last Late Nights, a series of live EPs dated by gig, the first of them 1/25/03. The bands on them read as a roll call of the era: pianist Jeremy Manasia on nearly every set, bassists Hans Glawischnig, Dwayne Burno, and Johannes Weidenmueller, drummers Ari Hoenig, Joe Strasser, and Daniel Freedman.

Owens left New York in 2004 and settled in Virginia, first around Charlottesville and then Richmond, and the move rebuilt his music from the rhythm section up. Beginning with A Day With Us in 2015 he worked as a trio with two players from the Richmond band Butcher Brown: bassist Andrew Randazzo and drummer Devonne Harris, who records as DJ Harrison. The group cut As One (2017) live to two-inch analogue tape at Montrose Recording, pushed further out on Three and Thirteen (2019), whose second volume hands Owens's arrangements to Randazzo's thirteen-piece R4ND4ZZO BIGB4ND, and reached its widest audience with 10 Years (2021), a set that runs Coltrane's "Central Park West" and Led Zeppelin's "Misty Mountain Hop" through the same jazz-funk vocabulary. Owens has kept a parallel acoustic quartet going as well, documented on Golden Moments (2022), and he returned to the SmallsLIVE label in 2018 for a quartet date recorded at the club on November 19, 2017 with Joel Frahm as second tenor, Alexander Claffy on bass, and Hoenig on drums.

He has not stopped commuting. Owens travels back to New York several times a year to play Smalls with his trio and quartet, and in Virginia he has become a fixture of the Richmond Jazz and Music Festival at Maymont, which he first attended as a spectator in 2016, first played in 2018, and once played twice in a single weekend in 2019 after another act cancelled. His 2024 album The Music Tells Us, cut at Spacebomb Studios in Richmond with bassist Cameron Ralston and drummer Kofi Shepsu, adds a Nord Stage 3 keyboard to his own instrumental role. He also works as a teaching artist in the Charlottesville and Richmond area, taking students from beginner to advanced in saxophone, piano, theory, harmony, improvisation, composition, and production.

Owens plays a big, unhedged tenor built on the postwar line he names himself: John Coltrane, Sonny Rollins, and Wayne Shorter. The Smalls years shaped the delivery more than any single influence did, because the late Friday slot rewarded volume, stamina, and long-form playing over neat arrangements; the club, as he described it, had no volume limits and no limits of any kind. What separates his Virginia work from his New York work is the rhythm section rather than the horn. Paired with Butcher Brown's Andrew Randazzo and Devonne Harris, he treats Duke Ellington, Coltrane, Led Zeppelin, Prince, Supertramp, and the Muppet song "The Rainbow Connection" as equally legitimate raw material, running all of it through a backbeat-heavy, organ-trio-adjacent groove while keeping the improvising firmly in a jazz idiom. His acoustic quartet records show the other half of the same musician: a straight-ahead player comfortable trading choruses with Joel Frahm on "Cheryl" at two in the morning.