Born in Detroit, Michigan, he grew up in the northern suburb of Berkley, Michigan. Crenshaw graduated from Berkley High School in June 1971. Crenshaw began playing guitar at age ten. From 1968 to 1973 he led the band Astigafa (an acronym for "a splendid time is guaranteed for all", a lyric from The Beatles' "Being For The Benefit of Mr. Kite"). He got his first break playing John Lennon in the off-Broadway touring company of the musical Beatlemania.While in New York, he recorded a single, "Something's Gonna Happen", for Alan Betrock's Shake Records, after which he was signed to Warner Bros. Records. Retro rocker Robert Gordon took Crenshaw's "Someday, Someway" to #76 in 1981, and Crenshaw's own version made #36 the next year; it would be his only solo Billboard Top 40 'Pop' hit. On the Cash Box magazine chart the song reached #31.