Harmony of Wine and Song

Singer Kristen Lee Sergeant ’04 has both a full-bodied wine label and a full-throated jazz career.

A photo of Kristen Lee Sergeant wearing an off-the-shoulder red top, smiling and looking down.
Jordan Frey
Kristen Lee Sergeant

On a sunny Tuesday afternoon in Manhattan, jazz vocalist Kristen Lee Sergeant ’04 is headed to a rehearsal for an upcoming show in Boston. But first she stops at Oak & Steel, an upscale wine merchant opposite Carnegie Hall.

It’s a special place for Sergeant, who worked there to make ends meet while starting out as a performer in New York City. Now it’s one of the specialty stores that carry Two Notes, a Bordeaux-style blend she created in 2016 with Grammy-winning saxophonist and composer Ted Nash.

At the store, Sergeant expertly swirls Two Notes in a glass and slowly sips the wine. The bottle is from the label’s second vintage, issued in 2019, a milestone that happily coincided with the release of her sophomore album, “Smolder.” “It’s pretty uncanny that they came out at the same time,” she says. “Both are creative projects I’m very passionate about.”

Sergeant launched a second career as a wine expert while finding her voice as a singer. “It’s been sort of a wayward journey,” she says.

Growing up in the small Massachusetts town Manchester-by-the-Sea, Sergeant loved the theater and was a professional actor by high school. In fact, she left her graduation ceremony early because she was cast in a local production of “Grease.” “I was wearing my costume under my gown,” she says with a laugh.

She briefly attended New York’s Wagner College, the University of New Hampshire and Harvard Extension School before transferring as a sophomore to Brandeis, where she studied classical music under Pulitzer Prize-winning composer Yehudi Wyner and was awarded the Ira Gershwin Prize at graduation. She says the university encouraged her to dive into different musical genres: “I was welcome to explore everything I was curious about.”

Sergeant moved to New York City after Brandeis, determined to pursue musical theater and opera. She performed in Shakespeare, Gilbert and Sullivan, and a rock opera about the Olympic figure-skating scandal involving Tonya Harding and Nancy Kerrigan.

Yet nothing felt quite right. “I realized everything I’d done was so I could sound like someone else, whether it was to fit into a composer’s vision for an opera or as a character in a show,” she says. “When you do that, you sacrifice individuality. I needed to figure out how I wanted to sound. I’d never asked myself that.”

In 2006, Sergeant’s roommate persuaded her to see legendary jazz singer Marilyn Maye — known for making more appearances on the “Tonight” show with Johnny Carson than any other entertainer in the program’s history — who was staging a New York City comeback. Sergeant was instantly hooked, captivated by Maye’s improvisational skills and intimate connection with the audience. “It was a turning point,” she says. “Something clicked. That was the kind of performer who really moved me.”

She began singing with a big band, taking lessons with jazz vocalist Tom Lellis and honing her technique at small gigs in the city. In 2014, Sergeant won the New York Jazz Forum Arts vocal competition. Two years later, she released her first record, “Inside Out,” and made her debut at the iconic Manhattan club Birdland. She’s also appeared at other NYC landmarks, including Dizzy’s Club, the Iridium, Joe’s Pub and the Metropolitan Museum of Art.

Along the way, Sergeant was working at Oak & Steel, imbibing everything she could learn about wine. She eventually became a certified sommelier, serving at the Grill, Gotham Bar & Grill, and other top Manhattan restaurants. The side job helped pay the bills as she put together “Smolder,” a fire-themed album composed of jazz standards, original songs and an arrangement of Spandau Ballet’s 1980s pop tune “True.” DownBeat magazine chose the album as an Editor’s Pick, noting in its review that “Sergeant’s training as an actress and classical vocalist enable her to craft moments of engaging drama, whether she’s seductively sliding into a note with a near-whisper, delivering a breathy revelation or belting out a lyric with full-throated muscularity.”

Meanwhile, Sergeant and Nash — who met as musicians and now live together in Upper Manhattan — discovered a mutual passion for wine and began talking about creating their own. The couple used Sergeant’s expertise to connect with a winemaker in Santa Barbara, California, who helped them develop Two Notes, a combination of Cabernet Sauvignon, Cabernet Franc, Petit Verdot and Malbec that retails for around $35 a bottle.

Coming up with the perfect blend was a true collaboration. “Ted prefers bolder California wines,” Sergeant says. “I prefer things that are more Old World. Left to our separate devices, the wine would not be as interesting as it is.”

Featured in Wine Enthusiast in 2017, Two Notes can now be found at select retailers, restaurants and jazz clubs in New York and Boston. Sergeant and Nash, who are looking to expand into other markets, plan to launch a second, lower-priced label. “This is not a vanity project,” she says. “This is part of our livelihood, something that we want to grow.”

In the meantime, Sergeant is working on her third album, which will include more original tracks. She’s also developing a stage show about the life of singer-songwriter Peggy Lee, whose husky voice elevated songs like “Fever” into hits. Sergeant is touring more, too, recently appearing at events in Los Angeles, Milwaukee, Minneapolis and Anchorage.

Occasionally, she sings at a venue that is serving Two Notes. “Not many performers get to have that particular thrill,” she says.

Heather Salerno is a freelance writer living in the Greater New York area.