Rachael and Vilray: Carrying a Torch

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 (footnote 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 (footnote 2). I definitely wasn't aiming for virtuosity. Music for me was always more about writing than guitar. Guitar is a means to an end, the end being songwriting. I am not a versatile guitar player." Which is and isn't true: Vilray is a deft, harmonically sophisticated rhythm guitarist, a complete accompanist capable of essaying the occasional solo.

"I graduated from LaGuardia by the skin of my teeth. I got my real education at Tower Records, where I spent all my babysitting money. It was a complete education for me, going through AllMusic's jazz guide, that big thick book of all the jazz CDs that were ever made, and circling things and falling in love, especially with sidemen. After I went through all those big-band settings, I went chronologically through the later stuff, from Bird to Pharoah Sanders, bop through hard bop through post-bop through '60s avantgarde."

Vilray then attended Boston's New England Conservatory of Music, majoring in jazz composition. That's where he met Price. He was selectively diligent. "I was very serious about cutting classes to spend time in practice rooms, tinkering around on piano or playing guitar. I was shedding composition. But I was only there for a total of two semesters over two years. I didn't come near graduating."

Returning to New York in 2005, he essentially quit music. "I felt like I couldn't hack it on an economic level." He took an accounting job in Long Island City. "I had musician friends who showed up on my doorstep and said, 'What's going on here? You should be playing.' I told them, 'I'm just a guy with a job now.' I was okay with that."

Breaking his finger, Vilray said, was like a divine warning shot. "It's as if the universe was telling me, in the kindest way possible, 'Your body is a finite, breakable thing. You'd better use it while you've got it.' In early 2015, a friend who booked shows at Bar Below Rye, a tiny club in Williamsburg, Brooklyn, told me, 'I'm going to book you for a gig three months from now, so start thinking about what you're going to play.'"

When the cast came off, Vilray took his brother's National resonator guitar into the Metropolitan Avenue subway station in Williamsburg, "a nice, reverberant space where I could get some confidence in my singing. This was toward the end of the long era of no cellphone reception in subways, so I had an audience. It was encouraging as hell because I learned I could get across. Women, mostly, would come up to me crying and say, 'My boyfriend just left me' or 'I just fell in love,' and that the songs really connected with them. It's a great thing to have your audience turn over every 20 minutes or less; you can play the same songs over and over and really hone them. I went after work three or four afternoons a week until cellphones penetrated the subway. I went from making $250 in three hours to a tenth of that. People were otherwise engaged."

By that time, he had played his comeback gig. He doesn't remember details, "but I think it went fine. It didn't make me want to never play another one." He began a casual run at Bar Below Rye, perhaps two shows a month.

Vilray and Rachael Price had stayed in touch, especially after Price moved to New York. "She tried to intervene, in maybe 2012, 2013," Vilray said. "She said, 'You like jazz, I like jazz, let's play together.' We did, but I was so rusty it just didn't go anywhere. I was in no position to play with anybody, let alone somebody of her caliber."

When Price heard he was playing again, she stopped by Bar Below Rye to provide moral support. "And that," Vilray said, "is how we got started."

Rachel Price with Lake Street Dive

During the decade when Vilray's career lay fallow, Price's career was gathering momentum. She and three other NEC students founded Lake Street Dive in 2004. The band scuffled until 2012, when a YouTube video of their sinuous, jazzy cover of the Jackson 5's "I Want You Back" went viral. Their third album, 2014's Bad Self Portraits, went to #18 on Billboard's Top 200. Their fifth, Free Yourself Up, peaked at #8, by which time Lake Street Dive was headlining festivals and packing auditoriums. The band's cardinal virtue is its highly collective nature—five accomplished musicians in a seamless blend—but Price's thrilling alto voice and wicked onstage shimmy are the big draw.

Price, 37, grew up in the Nashville suburb of Hendersonville, Tennessee. As a little girl, she fell in love with Ella Fitzgerald's voice. "From ages 5 to 15," she told me last autumn, "all I did was listen to Ella and learn her performances note for note." She was also inspired by Doris Day, a topflight 1940s big-band singer before she became Hollywood's cuddly housewife next door.

Raised in the Baha'i Faith, which she continues to practice, Price toured the world as a child soloist with Baha'i choirs directed by her father, himself an established, multifaceted musician. Several of those early performances have found their way onto YouTube, and they're astonishing.

As a teenager, Price studied at the Nashville Jazz Workshop, becoming intimate with show tunes and standards. "I learned probably 300 standards when I was a teenager," she said. "Those songs have never left me. It's like learning a language in childhood." Intent on a jazz career, she majored in jazz voice at NEC, studying with the influential Dominique Eade. "Until I worked with Dominique, I'd been only, really, copying my idols," Price said. "Dominique helped me strip away affectations, see what was left, and build from there."

In 2007, Price graduated into her own identity crisis.

"There were only a few career paths I could see as a jazz singer. It wasn't like in the '30s or '40s, when you could look at lots of different styles and imagine yourself falling into one." As much as she loved standards, Price couldn't see singing them for a living. "There wasn't enough authenticity in that. I was lucky to find myself in a band where everyone wrote original music"—where she invented herself after all, as a belter capable of tremendous subtlety. Her jazz background was a tremendous gift, providing her with a sonic palette that's broader, arguably, than any other rock singer today.

Still, a need was going unmet until Price dropped in at Bar Below Rye. "Vilray's performance reconnected me to jazz," she said. "It was one of those nights that is literally life changing. I was like, 'I don't want to do anything except sing with you in this bar for 25 people.' He said, 'Yeah, great,' and we started doing shows, and the vibe was perfect."

Vilray quit his day job and, due in large part to Price's star power, the duo rose quickly to the top of the cabaret circuit. Their first, 2019 album drew critical raves. Last November, they celebrated the second album's release with four shows at the ritzy Café Carlyle, where, since 1955, Bobby Short, Eartha Kitt, Judy Collins, and others have serenaded Manhattan's affluent.

Footnote 1: Bolles goes by his first name professionally; it's pronounced Vill-ree.

Footnote 2: Green was the Count Basie Orchestra's indefatigable rhythm guitarist.


Indydan's picture

Thank you Tony for writing such a great article about an awesome duo. I love their first album. I will very happily listen to the second one.

cafe67's picture

at the first sentence

Indydan's picture

Shouldn't you be watching Tucker Carlson?

mauidj's picture

So do you analyze every entertainers political actions and affiliations before you lend them your ears? How very right wing of you!

ThomasS's picture

Grabbed me at the first sentence. I know both Rachael and Vilray and can vouch for the accuracy of this account, which is very interesting and well-written.

jzh10's picture

The singing is lovely, and the new songs are often low-key subversive with humour - the message is why do women bother with men? Great stuff.
Looking forward to more live dates and really hopeful for a show in Toronto one of these days