Pickering began his music career playing guitar on the radio with a Milwaukee group called "The Westernaires" in the mid-1950s.

"[2] Prior to being in Our Gang, Nigel was a member of the folk trio The Folksters, who appeared on two 1962 episodes of The Tonight Show With Johnny Carson[1] (November 19 and 26).

The trio included Kenny Hodges,[citation needed] who later played in Spanky And Our Gang.

Pickering first met Spanky McFarlane and Oz Bach at a Hurricane party in Chicago, Illinois, in 1965.

[2] The three, along with Malcom Hale and John Seiter, formed Spanky And Our Gang, best known for songs such as Lazy Day, Sunday Will Never Be The Same, and Like To Get To Know You that were produced between 1967 and 1969.