By Jason M. Rubin

On To Oscar With Love, the jazz vocalist brings warmth, wit, and a fresh perspective to twelve songs by an underappreciated master storyteller.

Oscar Brown, Jr., whose centenary was October 10, was a poet, singer, songwriter, playwright, activist, and, most of all, a storyteller. It’s a shame that he was not more successful in his lifetime, and nothing less than criminal that he is largely forgotten today. Based in Chicago, he was not unknown nationally, but his many talents and refusal to compromise artistically seemed to limit his opportunities to become a bigger star (one of his songs is titled “Opportunity Please Knock”).

Brown was such a compelling storyteller that even his fans share stories about his impact and influence on them. Here’s mine. I was driving to Randolph, Massachusetts, one night, listening to the late Eric Jackson’s “Eric in the Evening” jazz show on WGBH radio. I was headed to my uncle’s house, where I was to present to my aunts, uncles, and parents my first draft of a eulogy for my grandfather, who had passed away just a day or two prior.

As I neared the house, Eric started playing a song of heartbreak that instantly captivated me – so much so that when I parked the car, I stayed put because the song was still playing. I wanted to hear the end and learn who the singer was. But Eric went wordlessly into the next piece, and I had a job to do, so I shut off the car and walked into the house. I was working at WGBH then, so the next day at work, I emailed him and asked who it was. It was Oscar Brown, Jr., and his epic “Rags and Old Iron.” Eric volunteered that when he was younger, the release of a new OBJ album was cause for celebration among his friends, and they would gather together to listen to it.

Los Angeles-based jazz singer Amber Weekes has her own stories of Brown, which helped inform her immaculate performances of twelve of his compositions on her new album, To Oscar With Love, which came out on August 7. This album is a much-needed tribute to the man, one that hopefully will introduce his music to a new generation of listeners.

“When I was a child, my family was driving somewhere when an Oscar Brown, Jr., song called ‘The Snake’ came on the radio,” she said. “My mother told me and my sisters to stop chatting and listen. Both my parents were singers and my mother also loved stories and knew the song had an important lesson that she wanted us to learn. That was the first song of his I heard.”

The song is about a woman who rescues a poisonous snake, which at first seems grateful but then bites her; when she asks with her dying breath why he bit her, the snake answers, “You knew damn well I was a snake before you took me in.” Brown’s fables almost always are a blend of wisdom and humor.

Oscar Brown, Jr. Photo: courtesy of the artist

Weekes grew up in musical household and, in her words, “I was pretty much born singing.” In addition to her parents being singers, her grandparents owned a luncheonette in the Sugar Hill district of Harlem that attracted customers such as Duke Ellington, Harry Belafonte, Sidney Poitier, and Diahann Carroll. In fact, Poitier romanced one of her aunts until her grandmother put an end to it, as she wanted the aunt to finish her social work studies. But that story informed Weekes’ singing of “Hazel’s Hips,” a song in which Brown deploys the “male gaze” toward a curvy waitress. With lines like “Hazel’s eyes are divine/And her hair is so fine/But her hips bring the tips,” the song presents a challenge for a female singer (the song was also covered by Chaka Khan).

“It is indeed the male gaze,” she said, “but I think it’s still a relevant story to tell, and at the end Hazel has the last word. Oscar Brown, Jr.’s songs are like mini-plays and the singer is a character and storyteller. I enjoy inhabiting these characters and adding my own voice to his songs, even though most are from the male perspective.”

A notable exception is “Strong Man,” which Abbey Lincoln asked Brown to write for her. Lincoln wanted to sing about good and kind men, rather than the drunken, unfaithful dogs that more typically are the subject of blues and torch songs. It is one of the highlights on To Oscar With Love, Weekes’ voice warmly conveying her appreciation for a lover who is “smiling between every kiss.”

Singer Amber Weekes. Photo: courtesy of the artist

With 125 published compositions to choose from, selecting just a dozen was hard work for Weekes, especially because Brown had such a deep and masculine voice and point of view. A small handful were originally recorded on her previous albums, suggesting that this project had been gathering momentum for a few years.

“There are some songs that as a woman I can’t do because it would misrepresent his lyrics,” she said. “But I wanted to do ‘A Ladies’ Man’ because it’s one of my favorites, so I brought in a male singer, Adam ‘Aejaye’ Jackson, to be the ladies man and I sang what became a narrator’s role. I did the same with ‘Rags and Old Iron’ by having him sing the part of the rag man. At the same time, ‘Work Song’ is a very profound song about a prison chain gang, yet when I sing it I’m able to bring in the perspective of a woman whose man was incarcerated, reminding people that the person in jail is not the only one impacted. It’s challenging because I want people to get to know me but at the same time I want to introduce people to Oscar.”

To Oscar With Love is Weekes’ fifth album as a leader; it was produced, arranged (strings and horns), and engineered by Mark Cargill (Dancing With the Stars, American Idol, Lady Gaga). Her backing band is stellar, as evidenced right away on the first track, “Mr. Kicks,” a bouncy number from one of Brown’s plays (hint: Kicks is Satan’s emissary). The musicians include Tony Campodonico on piano, Paul Jackson Jr. on guitar, Fritz Wise on drums, and several horn players.

The album works so well that I couldn’t help but ask if there would be a Volume 2. “Maybe,” she said. “I can tell you that this won’t be the last time that I record one of his songs. I’m going to do everything I can to keep his name and music alive.”

Weekes is planning a national tour and is hoping to include a stop in the Boston area. For more information, visit www.amberweekes.com.

Jason M. Rubin has been a professional writer for 40 years. He has written for The Arts Fuse since 2012. His books include SHORTS: A Sizable Collection of Short Fiction (2025); Villainy Ever After (2022), a collection of classic fairy tales told from the villains’ point of view; and Ancient Tales Newly Told (2019), a pairing of two historical romances, one set in 17th-century England and the other in Biblical Jerusalem and Sheba. Jason also teaches journaling workshops. He holds a BA in Journalism from the University of Massachusetts Amherst. Learn more here.