[2][3] As a young man, according to an interview with his daughter, Jennings was a dancer with the Billy Hicks Sizzling Six swing band and was a dance show promoter.
He always had a story and a whole lot of jive he swears his spiel can bring the dead back alive.”[6]The Call and Post job ended a little over a month after he was hired when he was in a serious car accident.
He covered the music scene, mostly jazz, under the heading of a weekly column called “Diggin’ the Scene.” He started a readers’ poll to select the best local bands, the best players on different instruments, and the best female and male singers.
Rowan of the Call and Post, while welcoming the new writer to that paper, had noted Jennings' complaints about how much his “Jive Colym” had been edited.
In one of his first “Jivin’ with Jennings” columns for the Tribune, titled “The Birth of Jive,” he wrote:“Many factors have contributed to the development of the English language since the days of Alfred the Great, King of the Saxons.
"He then offered a jive version of Hamlet's soliloquy beginning with “To dig, or not to dig the jive; …Jack, that is the question.”[11] Jennings’ time at the Tribune came to an abrupt end after just six months with an announcement on the front page of the paper that he and sports editor Kenneth Brown “are no longer connected with the Detroit Tribune in any capacity and are not empowered nor authorized to act for same.”[12] Jennings and Brown launched a magazine called Swingsation and produced one issue of a publication called The Word.
His artwork explored different themes, including portraits of jazz artists, streetscapes, children, flowers, and nudes.
A 1956 review of an exhibit of his pastels at the Grand River Art Gallery in Detroit noted that:“Most of his drawings impart a message for contemporary society, primarily the segment from whence he came.
He is a crusader on drawing paper, wanting to bring to the public eye the sordid environment that some children have to grow up in.”[13]A 1958 review of a one-man show of his oil paintings in Detroit commented:“The canvases are peopled with black, brown, and beige, youth and age.
Mixed with a little humor, a bit of terror, and a touch of beauty, the impact of Jennings’ paintings is refreshingly alive.
A spacecraft consisting mostly of a bass, with a cymbal, a violin, and the bell of a saxophone also forming parts of the craft, is in the reddish-orange sky above with a sax player on board.
Writer Carissa Kowalski Dougherty, in a 2007 article on race and jazz record cover design, said that Jennings’ artwork on the two Dolphy albums referenced the art of Salvador Dalí.
)[4]“The dreamlike qualities, visual distortions, and strange juxtapositions of Jennings’ landscapes reflect Dolphy’s particular brand of free jazz.
Surrealism may also have appealed to Jennings for other reasons; Richard Powell notes that several African-American artists, including Getrude Abercrombie and Hughie Lee-Smith, were drawn into a quasi-surrealist style because it allowed them to express their alienation for society.”[16]Jennings produced another more straight-ahead portrait of drummer and bandleader Max Roach used for the cover of Roach's 1962 album “It’s Time."
"[21] The video also describes Pryor shooting up his home, including a fish tank and a painting of Charlie Parker by Jennings (although it doesn't identify the artist).
In 1964, Jennings married Ann-Charlotte Dahlqvist, a Swedish flight attendant for SAS who had been a singer with a swing band in the 1950s.
Jennings died in Los Angeles on December 18, 2005, eight days after the death of his friend Richard Pryor.