The Little Boy Blues were formed in 1964 by Ray Levin(bass, piano), Paul Ostroff(lead guitar), Lowell Shyette(vocals, guitar) and James Boyce(drums), while they were attending the University of Illinois at Chicago. They started out playing Chicago Blues and songs like "Heartbreak Hotel." Lowell's neighbor, the owner of IRC records, heard the band and signed them to a recording contract soon after they formed. The record company wanted them to record in a more commercial style, so they dropped their blues style and recorded their first single with a British Invasion sound. The single featured two Lowell Shyette originals, "Look At The Sun" and "Love For A Day."
"Love For A Day" was heavily requested on local radio, which led to them becoming a popular opening act for big name bands playing in the Chicago area, including the Yardbirds, the Rolling Stones, Paul Revere & the Raiders, the Association, the Lovin' Spoonful and others. For these big shows, the band recruited Billy McColl as an additional vocalist, and to add excitement and stage presence to their live shows. They slowly evolved from a blues band into their classic garage-punk style.
In 1966, the Little Boy Blues released two more singles. The first was the Willie Dixon tune, "I'm Ready," backed with a Little Boy Blues original, "Little Boy Blues Blues." The second, "I Can Only Give You Everything," is one of their two classic fuzz-laden singles. They continued to play many live shows at Chicago area clubs including many performances at the Cellar in Arlington Heights, Illinois. They also became the house band at Like Young, Chicago's hippest teen club, where they played every Sunday night. They also made an appearance on Dick Clark's "Where The Action Is" television show. In 1966 Lowell Shyette left the band and was replaced by Frank Biner.
1967 brought the release of their fourth single (on Ronko), "The Great Train Robbery," backed with Donovan's "Season Of The Witch." The first was garage punk at it's best, while the second showed the band evolving into a more psychedelic style. As 1967 progressed, their sound got more psychedelic, incorporating jazz influences and flute. The Little Boy Blues were a leading counter culture band in Chicago, and played many events such as Be-ins in Lincoln Park and benefit concerts for the local underground newspaper, The Chicago Seed. They also played many shows at psychedelic clubs including the Electric Playground and the Cheetah in Chicago and the Electric Theater in New York. During this period, Billy McColl and Paul Ostroff left the band. They experimented with a succession of guitarists before settling on Peter Pollack.
On the strength of "The Great Train Robbery" they landed a contract to record an album for Mercury Records. Due to personal and artistic differences James Boyce quit the band, and after recording had commenced on the album, he convinced Frank Biner to leave too. These unexpected departures threw the band into chaos. Unwilling to lose the opportunity to record an album, Marc Coplon(vocals) and Bill Mooney(drums) were recruited, and recording continued. The loss of two key members caused the resulting album to be uneven and untypical of the Little Boy Blues sound. The band survived for about a year after the album was released, but didn't release any more records.