As Vilray Bolles marched down Manhattan’s Second Avenue on a rainy afternoon late in 2014, participating in a demonstration against police brutality, he slipped on the wet pavement, fell hard on his right hand, and broke his pinky.
For a guitarist, a broken finger can be a major, if not catastrophic, setback. But the gods were smiling on Bolles. He was, in fact, a lapsed guitarist, having all but abandoned hopes of a musical career, and the universe was giving him a nudge, not just back into music but into a collaboration with Rachael Price, one of contemporary pop’s great vocalists, who, when she isn’t singing cabaret jazz with Bolles, fronts the headlining rock band Lake Street Dive.
Rachael & Vilray have just released their second album together, I Love a Love Song!. Like its predecessor, it consists almost entirely of songs written by Vilray,1 who has a gift for writing songs in the manner of Cole Porter or Harold Arlen—songs composed, as John Updike put it, “in decades when Americans moved within the American dream.”
Born and raised in Brooklyn, where he still lives, Vilray, 38, is “old French American on my father’s side,” he told me when we spoke last fall. Vilray’s mother, who is Nicaraguan, gave him his first guitar when he was 9. He attended Manhattan’s storied Fiorello H. LaGuardia High School for Music & Art and Performing Arts, the setting for the 1980 movie musical Fame.
“High school is the moment I discovered jazz,” Vilray told me. “We were playing big-band jazz for the most part, so I was doing what I’m doing on this record, which is Freddie Green–style quarter-note comping. I definitely wasn’t aiming for virtuosity. Music for me was always more about writing than guitar. Guitar is a means to an
