Born in 1959 in Wichita, Kansas, Eskelin grew up in Baltimore, Maryland with his mother Bobbie Lee, a Hammond B-3 organist who led her own jazz groups during the '60s. His father, whom he never met, was cult song poem musician Rodd Keith. Eskelin began playing the tenor saxophone when he was ten years old and soon after began learning how to play jazz. By the time he was in high school, he was already playing professionally, buoyed by week-long summer jazz camps led by Stan Kenton & His Orchestra that he attended annually at Towson State University. After high school, he also studied at Towson before moving to New York City in 1983. It was during this period that he studied with saxophonist David Liebman. He made his recorded debut with 1987's Joint Venture, a quartet date with trumpeter Paul Smoker, bassist Drew Gress, and drummer Phil Haynes. The following year, he appeared with the same group, minus Smoker, for Setting the Standard.
In 1990, Eskelin again recorded with Gress and Haynes on Forms. He then joined tuba player Joseph Daley and percussionist Arto Tuncboyaciyan for Figure of Speech. The solo saxophone recording Premonition arrived on Prime Source in 1993. Around the same time, Eskelin formed a trio with keyboardist and accordion player Andrea Parkins and drummer Jim Black. Together, they released a series of zany, yet structurally inventive albums beginning with 1994's Jazz Trash. Eskelin and Parkins also paired as a duo for 1997's Green Bermudas before reuniting with Black for 1997's One Great Day... and 1998's Kulak, 29 30.
On his own, Eskelin continued to put together increasingly varied projects, including 2001's Vanishing Point with violist Mat Maneri, cellist Erik Friedlander, and bassist Mark Dresser. He then returned to his trio with Parkins and Black for 2003's Arcanum Moderne. In 2005, he marked the tenth anniversary of the trio with Ten. He then paired with pianist Sylvie Courvoisier for the 2008 duo album Every So Often. Another duo album, Inbetween Spaces, appeared in 2010, this time with drummer Gerry Hemingway. He joined fellow saxophonist David Liebman for 2012's Non Sequiturs, followed by several live albums. He also appeared on 2012's Dirigo Rataplan, playing with trumpeter Dave Ballou, bassist Michael Formanek, and drummer Devin Gray. 2017's Sensations of Tone found him working in a trio setting with bassist Christian Weber and drummer Michael Griener. The same group returned in 2019 with Pearls. ~ Matt Collar, Rovi