His twenty-five years of playing experience has involved performances with Wynton Marsalis, Eartha Kitt, Michael Brecker, Slide Hampton, Wycliffe Gordon, Chuchito Valdes, and the New York Voices. Other Indianapolis and Midwest-based performers with whom Kenny has worked and recorded include the Debarge Family, Rob Dixon, Pharez Whitted, Fareed Haque, Derrick Gardner and Melvin Rhyne. For several years, he played in a trio with Frank Smith and pianist Frank Puzzullo at a downtown Indianapolis restaurant. Starting in 2009, he was active in a family fusion band, Hananeel, with his brother, a nephew and others.

In 2011, Kenny purchased Owl Music Group, an outgrowth of Owl Records, a local jazz label. A year later, he became Owl’s CEO, turning the company into a humanitarian arts organization reaching out to young musicians and community organizations such as the Julian Center and the Wheeler Mission Ministries. The Community Outreach arm brings music to these agencies and supplements the concerts with served meals. The Night Owl Session, is devoted to enriching the lives of youth through music education, engagement, and entertainment. In collaboration with public-school systems, it provides mentoring and direction to aspiring instrumentalists and singers considering music as a career. All facets of the music industry are explained to participants, while the core emphasis is motivational. “We encourage them to jump into their passion for music,” says Kenny, “but also let them know that struggle and sacrifice are needed.”  Since 2016, Phelps has been an adjunct jazz percussion instructor at Butler University.