Rainbow Jimmies is largely devoted to Gray Cottage Studies, composed for Todd Reynolds. The seven studies, scored for violin with vibraphone and/or drumkit, were written by Hollenbeck while at the Blue Mountain Center arts retreat in the Adirondack Mountains. He credits “early morning canoe trips, the deer, the residents and staff” as inspirations.

Reviewing Rainbow Jimmies in All About Jazz, Troy Collins wrote, “Hollenbeck's compositions always bear the distinctive stamp of his singular style – an eclectic but cohesive amalgam of advanced jazz harmonies and post-minimalist rhythms bolstered by tuneful melodies and driving rock-like intensity. Revealing a keen ear for melody… These introspective variations reveal Reynolds' lyrical virtuosity as he unfurls bittersweet cadences ranging from austere to soulful, interweaving with Moran's scintillating accents and Hollenbeck's subtle interjections.”