Cleveland, late 1950s-early 1960s
1956 ad, from Detroit/Windsor, ON, with Cleveland's Hornets
Not a lot of details available on Skippy Roberts. He is mentioned a few times in the Plain Dealer from 1959 until 1963.
He recorded two 45s that we know about. The first one was a local release on the Pett label, which is probably related to the songwriters J. Petrella and M. Petrella. The record is a R&Bish rock and roll record, well produced, likely recorded at Audio. The publishing is Reserve which means there is probably some connection to the Reserve label.
The second 45 came out on the Lark label from Los Angeles. It's a stronger rocker with Skippy showing a wide vocal range. The sax and guitar playing is pretty aggressive, we defintely want to know who they were!
One of the PD bits lists Skippy performing as part of a "modern jazz concert" led by well know saxophonist Joe Alexander and including the Four Jacks who are credited on the Lark 45, they are the backing vocal group, it seems.
His last PD mention is Skippy playing Leos Casino in 1963.
Little Pumpkin / Rock 'N Roll 'N 45 - Pett no # (RCA master J8OW-3370/1), 1958
Holy Mak'Ral Andy / Brown Sugar - Lark 457, May 1959