Leonard was born on March 14, 1956 in Crystal Falls, Michigan. He entered the music business with late 1970s Chicago-based pop rock band Whisper, then later the same band membership, Trillion (name changed for legal reasons), featuring future Toto singer Dennis “Fergie” Frederiksen on lead vocals. His early career also featured short stints as a keyboardist in Frank Zappa’s band in 1976 and The Allman Brothers Band in 1980.

He went on to act as musical director and lead keyboardist for the Jackson Victory Tour in 1984.

“The Lamb Lies Down on Broadway, Dark Side of the Moon, The Wall – that’s what I grew up with and that’s what I dreamed of doing one day,” he recalled in 1992. “I was a big Gentle Giant fan. I was a huge Jethro Tull fan. But I had to feed my children and heat my house, so I wrote some songs with a little girl who became extremely popular. It’s really that simple.”