That could change with his most recent releases, especially the single released on Madjack Records this March, "I'll Be the One" b/w "People." Unlike the raunch 'n' roll purveyed by Jack Oblivian, this solo release is unabashedly happy-go-lucky pop. The A-side, for example, certainly sounds like an A-side, and could make for a potential hit if this was the 60s or the 80s. (Or maybe now, what do I know?)
The tradition of power pop in this city is a rich one, even if it's sometimes overshadowed by the blues, soul, and rock 'n' roll. Winchester's bouncy take on a declaration of love would fit right in on an album by Good Question, the group started by local pop-meister Van Duren in the early 80s. Giving it that extra 80s shimmer are some tasty synth licks that are nestled in the guitar-driven track.
The flipside mixes a slower bounce with a trace of poignancy, as Winchester croons about humanity in a more wistful manner, like a cross between Herman's Hermits and the Kinks. The warmer, more traditional sounds of piano and organ dominate this one, in keeping with its earlier touchstones, and in a way it's more affecting than the A-side. The extra touch of vulnerability draws you in.
Winchester is nothing if not prolific, and there are more recent releases to be heard as well. While the aforementioned tracks are on a physical release, the new tracks on Bandcamp are clearly post-coronavirus, solo excursions on acoustic guitar. Both "Fortune Favors the Bold" and "I'll Be Sad With You" go a long way in demonstrating Winchester's eclecticism, exuding a mellow folk melancholy that is especially cathartic in these quarantined days. "Fortune" is especially moving, a portrait of a spurned lover blindsided by rejection and striving to make sense of it all. Musically, it's more venturesome as well, dipping into some fascinating dissonance in the coda that adds further shadows to the mood.
Winchester has been ahead of the live-streaming curve since shelter-in-place began, and that may be the perfect place to hear these songs in the context of his wide-ranging songwriting chops. As an everyman singer with a restless imagination, there's no telling where he's headed next.