
Whiteside was a gifted singer who learned his craft on the streets of Queens starting at the age of 13 singing in Doo Wop groups. Over the next five years, he learned to not only sing lead but also all four support parts (bass, baritone, 1st tenor and 2nd tenor).
Not to be limited to just his voice, Kenny also learned to play jazz drums and, but the age of 18, he was singing in his own group and playing drums in bands including one of the youngest jazz ensemble to ever play at Birdland.
Over the decades, Whiteside became known as a versatile entertainer, not only performing as himself but also in tribute performances to Elvis Presley (The Echos of Elvis Tribute), Jackie Wilson, Marvin Gaye, Barry White (all in Soul Lives On Tribute), Engelbert Humperdinck and Dean Martin. In addition, Whiteside also had a vocal training business.
Kenny joined the Cleftones in 1997, singing both lead and background vocals, joining original lead Herb Cox, Mac Todd (who also joined in 1997), Kevin Jeter and Nick Saunders who has been with the group since 1970. Whiteside can be seen in the group's appearances on the PBS Doo Wop specials and heard on the 2002 album The Cleftones: Live Today. He remained with the group until just recently when his illness forced him to the sidelines.
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