Through the 20th century and into the 21st century, a string of African-American male singers have graced stages throughout the United States — singing the blues; crooning smooth ballads, cigarette in hand; jumping up and shouting until the lights went out; and singing jazz standards and bebop lyrics hard in the groove. However when it comes to explicit songs of African-American daily life, no one’s has covered a broader vocal canvas than Oscar Brown, Jr. — the songwriter, poet, civil rights activist, actor, essayist and playwright.

Coolness and the “Signifyin’ Monkey”

I became aware of Oscar Brown in my sophomore year at Evander Childs High School in the “Boogie down Bronx”. At that time, in order to sit at the table for cool kids, there was a prerequisite — know the lyrics to “Signifyin’ Monkey.” I had never heard the song or knew anything about the singer/lyricist Brown. It was one of the songs from his debut album Sin & Soul (Columbia Records, 1960). The song is funny as hell because of its moral ending: don’t talk stuff to people bigger than you, especially if you know they can kick your butt; and always remember that the monkey is always looking to start some mischief. In African-American folklore, the monkey symbolizes mischief and trouble making; his humor could easily lead to catastrophe.

After getting album title from Vance, the senior, who made memorizing the song mandatory to coolness status, I immediately went out and purchased a copy. After listening to the album day and night, I finally had it memorized. Knowing the lyrics to the song added to my standing at the coolness table. Most importantly, the girls sitting at nearby lunch tables got a kick out of us singing the song in unison, even though, we may not have done so in the same key.

Ironically, while memorizing “Signifin’ Monkey,” I fell in love with the entire album and memorized most of the songs. The 12 songs (10 original and two covers) are all treasured gems that circle joys and sorrows, reflecting the realities of the “humdrum blues.” African-American life songs so descriptive that they will damn near bring you to tears . Listen to the lyrics of “Like Rags and Old Iron” or “Somebody Buy Me A Drink”. While in others, they are so humor full you may fall off your chair from laughter. Or there are a few like “Afro Blue” which may have you humming in unison.

Penning Words to Composers’ Instrumentals

On this debut album, Brown penned his lyrics to such noted instrumentals, Cannonball Adderley’s “Dat Dere” and Nat Adderley’s “Work Song” and Mongo Santamaria’s “Afro Blue.” Nina Simone later recorded his lyrics of “Afro Blue,” “Work Song” and “Bid’em In.” The pioneer gospel singer Mahalia Jackson’s recording of his “Brown Baby” went straight to Baptist church pews (there is no better lullaby your bouncing baby).

His lyrics like Langston Hughes‘ and Amiri Baraka‘s captured the real spirit and soul of African-American life from his bouncing baby girl “Maggie” to the slaves’ selling block “Bid’em In.” Yes, he sings vividly of that promised “Forty Acres and A Mule.” Brown’s songs represent the fundamental elements of African-American music; the oral storytelling of the ancestors, from the cadence of field negroe’s call and response to gospel, the blues and swing.

Meeting Oscar Brown in Person

It was years later at the Cape May Jazz Festival (Cape May, New Jersey) where I met Oscar Brown, Jr. after his performance at the after party. Carol Stone, the festival’s co-founder introduced us. I was in awe. Wow, is it really Oscar Brown, Jr.? Yes it is, somebody please slap me. During our conversation, I proudly gave Oscar the whole high school “cool”story. He thought it was funny and cool at the same time. At the end of the night, we agreed to meet for breakfast the following morning. There was no sleep for me that night. Waiting to have breakfast with my idol was just too much.

At breakfast, he was smooth, hip and dedicated to the struggle. He said to me, “The struggle lives in my music, the lyrics are my bullets against injustice.” The following year, fortunately for me, Brown returned to the festival. For those following few days, breakfasting together became our ritual. In the years that followed, we often communicated with each other, even though, he lived in California and me, in the Big Apple.

Popular Interpretations of Oscar Brown’s Works

Brown’s lyrics could be statements about lackadaisical governmental policies or beautiful songs softly flowing in the African diaspora, “Afro Blue” for example has been performed by songstresses Dianne Reeves, Dee Dee Bridgewater, and Lizz Wright. Vocalist Karrin Allyson was so inspired by Brown’s lyrics, she recorded several of his songs. Before his death, Brown was scheduled to contribute lyrics to Allyson’s 2006 album Footprints; instead, as a tribute, she recorded his songs “A Tree and Me” and “But I Was Cool.” Many jazz singers have sung Brown’s lyrics to “Jeannine” — the most popular presentation was by vocalist King Eddie Jefferson, the melody was composed by pianist Duke Pearson. Pianist Wynton Kelly recorded Brown’s “Strongman” (Piano Riverside Records, 1958) with his trio.

The year 2004 was big for New York City, it marked the premiere opening of Jazz at Lincoln Center. As an honored guest, Brown joined the dynamic poet Sonja Sanchez in performing one of his poems. JALC has become one of the most influential jazz institutions in the world and fittingly Brown was a part of that great opening.

His first recorded work was a collaboration with another outspoken musician the drummer and composer Max Roach. Max’s composition We Insist! Freedom Now Suite (Candid Records 1960) was directed at the United States during the civil rights movement.

As a playwright, Brown attempted to launch his musical stage production of Kicks & Co., in New York City (1961). Although the play was not a financial success, it did receive critical acclaim, due in part to the participation of a young Muhammad Ali, in the role of Buck White.

Oscar’s coined term “edutainment” was the driving force behind his lyrical and cultural revolution. While Brown was singing the truth from equality to love, Columbia Records was trying to figure out where this genius of an artist musically fit in. Was the category “easy listening” or jazz? Since they didn’t have a clue Oscar’s contract was not renewed.

The Original Gansta Rapper and Politics

Brown penned over 1,000 poems; an abundance of songs  — 125 have been published; wrote over a dozen musical stage plays, several of which are written entirely in rhyming verse; and recorded 12 albums. Brown was a hip intellectual and a street cat whose knowledge was shared through his music from the pulpit to the street. It was a writing career that spanned over a half a century. He was the original gangsta, laying the road map for Tupac, Ice T, NWA, A Tribe Called Quest, and even Will Smith’s soft rap.

His multi-faceted music was the recorded soundtrack of a racist stained America. It led him to run for a seat in Illinois state legislature, and, for a seat in the U.S. Congress. He is probably the first jazz musicians to ever run for political office. Although he didn’t win, he, like former Presidential candidates Shirley Chisholm, Jesse Jackson and Rev. Al Sharpton, made a point for awareness of unfair racial conditions in the United States.

Little did I expect that a high school cool experience would lead me to meet my jazz-singer-idol Oscar Brown, Jr. and become a friend of his. Wow! For me, the song that best describes this lyricist and singer is “But I Was Cool.” He was always that plus respectful, insightful and friendly.

Check out his video performance Oscar Brown Jr. & Friends – JazzBaltica 1998.