Amber Weekes grew up hearing stories about her grandparents’ luncheonette from her father and his sisters, who often worked the counter in the decade after World War II. The family enterprise often manifested the African-American genius that was woven into the neighborhood fabric, serving as a stage when Sugar Hill grooved to a soundtrack that reverberates no less brilliantly today.

“It was a place where the community gathered, and you had all these amazing, creative people all together in Harlem,” says Weekes, a poised and incisive jazz vocalist with infuses every song she touches with her ebullient spirit. “Duke Ellington lived around the corner and would come by for a bite in the wee hours after a show. Lena Horne and Sonny Rollins lived in a building nearby. Sidney Poitier and Harry Belafonte were just starting their careers and they came by to eat all the time.”

More than a collection of songs, ‘Round Midnight – Re-imagined is Weekes’ musical portrait of that luminous moment, filtered through her family’s memories. Working closely with a stellar cast of Los Angeles jazz players and producer, arranger, and conductor Mark Cargill, she sets the scene and fills it with vivid characters, evoking the looks, inner lives, and personalities that could be found in Weekes Luncheonette and its environs. The journey commences on a warm summer night, inspired by the glittering Gotham fairytale that her late father, Martin Weekes, conjured with his stories.

The album opens with a rollicking arrangement of Oscar Brown Jr.’s “Hazel’s Hips,” delivered by Weekes with a knowing wink. Her sly performance is dedicated to the thwarted romance between then-unknown Sidney Poitier and her Aunt Dolores, who was waitressing at the Luncheonette when they met. Engaged but never married due to Nettie Weekes’ disapproval—“She was afraid that my aunt, who was attending Hunter College at the time, would forever have to support a struggling actor,” Amber says—Poitier mentioned Dolores and her sisters in his 1980 memoir This Life, describing her as “The Angel of the Luncheonette.”

That irresistible family tale gives way to a wider focus with the bossa nova standard “Summer Samba,” a sensuous arrangement that captures the tingling excitement of a new romance. From earthy pleasure to sacred promise, Weekes glides through the neighborhood to contemplate the Cathedral of St. John The Divine, an imposing Harlem landmark. In a dedication to her mother, Weekes offers up a sublime prayer in the form of pianist Duke Pearson’s “Cristo Redentor” and the Negro spiritual “I Want Jesus to Walk With Me.” That’s guitar legend Phil Upchurch offering a sorrowful benediction.

Weekes’ gift for developing thematic medleys is another thread running through the album, with Sting’s winsome “Sister Moon” pairing artfully with the beloved Porgy & Bess lullaby “Summertime” (effectively arranged by pianist Bob Remstein). The bittersweet medley takes us Downtown, catching a young couple in Battery Park, gazing upon the “lights of the River Hudson.” Weekes borrows the line and the moment from a poem written by her father at 16 while riding on the Staten Island Ferry with then-girlfriend Marpessa Dawn (who gained international fame as Eurydice in the Academy Award-winning 1959 film Black Orpheus).

Rodgers and Hart’s “My Romance” and the classic blues “Don’t You Feel My Leg” (a song immortalized by New Orleans great Blue Lu Barker) aren’t a medley, but they offer a yin/yang perspective on the pursuit of pleasure. The former is an intimate duet with pianist Eddy Olivieri celebrating the quiet intensity of a cocooning couple. Cargill’s supple string arrangement accentuates Weekes’ lustrous, swooning vocals, much as Dwayne Benjamin’s trombone provides a lusty counterpoint to her lowdown vocals on the latter track, which takes us to a smoky club where a blues singer regales a group of buddies out on the town.

The album’s emotional centerpiece is The Bar Suite, a bibulous tryptic inspired by her father’s love of Frank Sinatra. The three songs introduce Weekes’ primary character, catching up to her in the middle of a warm summer day as she wanders into a bar for “Something Cool.” Weekes possesses a lovely sound, warm and fine-grained in every register, but her deft navigation of the piercing narrative makes it clear that she’s also a captivating musical storyteller.

A seamless segue into what Sinatra called the ultimate saloon song, “One For My Baby,” goes down like smooth whisky, setting up “The Man Who Got Away,” a song that Weekes’ father sang so often (as “The Gal Who Got Away,” a la Ol’ Blue Eyes) that it’s almost a tangible part of her childhood.

The album closes with a series of vignettes. A giddy couple saunters down Park Avenue in Natalie Cole’s “Lovers,” delighting in each other’s company. Our sad friend from The Bar Suite wobbles back to her Long Island digs for a lonely, late-night reverie with “Round Midnight” while hoping for a reunion with her lover. Olivieri accompanies Weekes as the curtain closes with a besotted duet on the 1929 standard “More Than You Know,” offering the denouement of your choice. “Is this a newly engaged couple?” Weekes says. “Did our Lady from Long Island hear a key in her door? You decide.”

She may leave the last choice in the hands of her listeners, but Weekes is fully in command throughout the album. Her most ambitious project yet, Round Midnight – Re-imagined is the work of an artist with a powerful vision and the creative resources to bring it vibrantly to life. She recorded the skeleton of the album some 15 years ago when it was essentially a calling card for festivals and venues. It was only during the pandemic that she and Cargill decided the time was ripe to fully flesh out the concept, expanding the arrangements with strings. The result is a document of an unforgettable time and place by a singular artist.

A singer from earliest childhood, Weekes grew up in a home suffused with music. In addition to being a fine singer who idolized Sinatra, her father was a trombonist. Her mother also possessed a highly musical ear. “They both wanted us to pay attention to the lyrics and would make us sit down and really listen,” she recalls. “I was a kid, but the stories meant something to me.”

Early on she studied with the esteemed jazz pianist/arranger Phil Moore and his wife, vocalist Jeanne Moore (now Jeanne Pisano). A devotee of the American Songbook, Weekes was also drawn to more contemporary material, forging a particularly strong bond with the music of Oscar Brown Jr. Under the wing of the great, but often overlooked LA jazz vocalist Sue Raney, she developed her own sound.

Weekes has made a name for herself on the talent-laden Southland jazz scene in recent years with riveting performances and her critically hailed 2019 debut album Pure Imagination. She quickly followed up in 2020 with the tasty holiday album The Gathering. Unwilling to let the pandemic keep her down, she felt the time was right to fully realize her vision for ‘Round Midnight, thus the project was Reimagined. Summoning the resilient spirit of an era that can feel like a distant world, the album is “a gift of love and music and healing,” from an artist who brings that glorious past into our uncertain future.

Andrew Gilbert is a Berkeley-based music writer who covers jazz for the San Francisco Chronicle, San Jose Mercury News, and KQED.