Growing up in Massachusetts, Kenny joined his first band at age ten. At the time a self-taught drummer, he played in local bands throughout junior high and high school, playing rock 'n' roll. At sixteen, he decided to focus on classical music, and began to study seriously with members of the Boston Symphony Orchestra. He went on to study at the University of Massachusetts and at Indiana University, where, among other honors, he was awarded the school's prestigious Performer's Certificate. During the summers, he participated in the Aspen and Tanglewood Music Festivals.
After graduating from Indiana University in 1976, Kenny passed on several offers of timpani positions in other countries, and decided to head for the East Coast, where he studied drum set in Boston and New York. During this time he began to concentrate on jazz and fusion music, and in 1977 he returned to Bloomington, Indiana and spent several years in a popular local band, playing throughout the Midwest. He eventually heard of an opening in another Indiana band, and in 1980 he began a long and extraordinarily productive relationship with John Mellencamp.
In the Mellencamp band, Kenny developed a powerful and innovative style. His solid backbeat became the driving force behind Mellencamp's long run of definitive hit records. During time off from the Mellencamp band, Kenny developed an enormously successful career as a studio musician, playing on hundreds of records, and doing live shows and tours with many different artists.
In recent years, Kenny has played major tours with The Smashing Pumpkins, Bob Seger, Melissa Etheridge, John Fogerty and Joe Cocker as well as many limited promotional dates for a wide variety of artists. In addition, from 1993 to 1997 Kenny was an Associate professor of Percussion at Indiana University.