Jennings, Lyfe

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Lyfe Jennings


Singer, songwriter

Lyfe Jennings is a singer and songwriter, crafting emotional ballads with a unique sound that blurs the lines between R&B, hip-hop, and folk music. The platinum-selling recording artist is also a multi-instrumentalist who plays guitar, bass, and piano. Critics have called Jennings a throwback to the R&B singers of the 1960s, including such legendary artists as Sam Cooke and Al Green, while his use of hip-hop beats and collaborations with rappers connects his music to contemporary developments in R&B. Some critics have even credited Jennings as a pioneer of a new genre; one that National Public Radio (NPR) host Corey Moore called "Folk Soul." Building on the success of his debut, Jennings released two additional albums, gaining fans and prestige with each release and helping to define a new generation of R&B music.

Spent Ten Years in Prison

Chester "Lyfe" Jennings was born on June 3, 1973, and raised in Toledo, Ohio, where he and his four siblings—sister Dawn and brothers Charles, Jay, and Paul—attended the city's public schools. Jennings's interest in writing and playing music began when he was in elementary school, and he performed with the choir at Cavalry Baptist Church. Before he was in high school, Jennings was already writing his own songs. "I've been writing since I was little," Jennings said in an interview with Rhonda B. Sewell in the Toledo Blade in 2003. "You need an outlet for the problems that you face, and I went through all the things associated with the streets."

Jennings's uncle, Keith Dotson, was a working musician who sang with the Toledo Motown group KGB. In the 1980s Dotson's sons Tim and Chris formed a teen singing group, which they called The Dotsons, and asked Jennings, then ten years old, and his brother Jay to join the group. The Dotsons wrote and performed songs reminiscent of the popular R&B vocal groups of the time like Troop and New Edition and were popular at local talent competitions. Though successful in the local circuit, The Dotsons eventually disbanded as Jennings and his family members drifted apart. Jennings became involved in crime, and at age nineteen he was convicted of third-degree arson and sentenced to prison.

Jennings remained in prison for almost ten years, having failed his parole evaluations, but found ample time to work on his music. He sang with a prison gospel choir and learned to play the acoustic guitar, the only instrument he was allowed to use. "When I was in jail, I did a lot of soul searching," Jennings said to Brandi Barhite in the Toledo Free Press in 2008. "I set myself some goals and that translated to music." In 1997 Jennings received a copy of Erykah Badu's album Baduizm and, in listening to Badu's introspective compositions, began developing songs that explored the more philosophical side of romance, urban life, prison, and the African-American experience.

Performed on Showtime in Harlem

Though Jennings was incarcerated until December of 2002, he found a receptive audience among his fellow inmates. As his release drew near, Jennings decided on a new goal, to perform live on Showtime in Harlem, a televised musical variety competition produced at the Brooklyn Academy of Music. Jennings convinced prison administrators to allow him to film performances given to audiences of inmates and was allowed to send his audition tape to the show's producers. Two days before his release from prison, Jennings received word that his audition tape had been accepted. At twenty-eight years old, Jennings thought that he had little time to waste, though he had learned to accept the limitations that prison had placed on his development. "You start your career when you start it," he told Barhite.

Jennings chose the stage name "Lyfe," to reference the trials of life and to his tendency to ask the question "why" in his compositions, he explained to Sewell. Two days after his release he recorded a four-song demo album, and a little more than three weeks later he performed before an audience of millions on Showtime in Harlem.

In 2005 Jennings told Corey Moore in an interview on NPR that the Showtime audience seemed skeptical when he walked on stage, unsure how to respond to an artist who looked and dressed like a rapper but was carrying an acoustic guitar. Jennings eventually won the audience over, and he won the Showtime in Harlem talent competition after five rounds, gaining confidence and fans with every performance. Jennings sold and distributed his four-song demo album at his performances and later recorded additional tracks to form a full EP called What Is Love?, which he distributed at his concerts in New York and back home in Toledo.

After Showtime in Harlem Jennings began touring, and he received offers for recording contracts from a number of prominent studios. Jennings won a promotional deal with the Budweiser brewing company and was asked to perform at a convention for the National Association for the Advancement of Colored People (NAACP). In 2003 he moved to New York City and settled in Brooklyn, where he continued performing and shopping his demo to record companies. Before he was signed to a recording contract, Jennings had already been asked to perform as an opening act for hip-hop performer Nelly at Radio City Music Hall.

Produced Own Debut Album

Jennings signed a record deal with Sony Music Label Group U.S. in 2003. Sony president Don Ienner told Gail Mitchell in an interview in Billboard magazine in 2005 that he only listened to three songs before deciding to offer Jennings a contract. Sony executives were uncertain how to market Jennings, whose style placed him between R&B and hip-hop audiences. In addition, Jennings's sparse instrumentation and delivery were more in keeping with folk music. "I play the guitar and tell stories about real life," Jennings told Mitchell. "That's close to what folk singers do. But my lyrics lean toward rapping."

Sony executives eventually decided to let Jennings produce his own album, a feat that is uncommon for emerging artists. "We knew it was a creative risk," Ienner told Mitchell. "But we wanted him to make a statement in his own beautiful voice and in the way he reads his lyrics. Anything else would not have been authentic." The title of his debut album, Lyfe 268-192, which was released in August of 2004, gave homage to the identification number he was given in prison. Sony kept Jennings on a grueling touring schedule throughout 2004 in an attempt to foster sales, and teamed him up as an opening act with fellow alternative R&B singer John Legend. The single "Must Be Nice," became a top-forty hit and entered Billboard's Hot R&B/Hip-Hop Singles and Tracks top five category.

At a Glance …

Born Chester Jennings on June 3, 1973, in Toledo, OH; son of Sandra Temple; children: Phoenix, Elijah.

Career: Singer, Sony Music, 2003—.

Addresses: Office—c/o Columbia Records, 550 Madison Ave., 24th Fl., New York, NY 10022-3211.

That Jennings's album was successful despite a lack of recognized producers and guest appearances was evidence to many critics of his talent and originality. Billboard called the debut an "anti-bling album." The record went gold, reaching sales of more than 500,000 copies, in the summer of 2005, and Sony continued to push Jennings with an aggressive online promotion and summer touring schedule. In addition, the label produced a special double-disk version of the album with live footage and interviews on the second disk.

Though Jennings's story and time in prison were an obvious selling point for urban youth who respond to the criminal image, Jennings refused to either glamorize or diminish his experiences. "I'm from the streets and I'm writing for the street cats," Jennings told Sewell in 2003. "I want to tailor my message for people in the streets so that they can take something away from my music." Though he meant his music for the urban consumer, Jennings also paid tribute on several tracks to his religious convictions. The name of his production company, Jesus Swings, also honors the role of faith in his life.

Achieved Recognition as a Breakthrough Artist

Jennings's sophomore album was also self-produced but featured a more modern, urban sound with less of the simple instrumentation that drew comparisons to folk music after his first album. On his second release, The Phoenix, which was named in honor of his son, Jennings tackled a number of potent sociological issues, such as marital relations and underage sex. "There's a moral core at the center of Toledo soul man Lyfe Jennings' work that is so strong it threatens to overwhelm his potent rhythm and blues music," said Rod Lockwood in a review of Jennings's second release in the Toledo Blade. The album debuted at #2 in Billboard's Top 200 albums.

Jennings returned to Toledo's City Park to shoot a music video for the single "S.E.X.," and, as he told Michael Punsalan in the Toledo Free Press, hoped to make his hometown a more important focus of his career. "I want to start shooting more videos in Toledo and let people see the landscapes and different textures that we've got," he said. "I want to continue putting out music to the best of my ability, but I also want to do things like a nonprofit organization in Toledo to build the community up. Like rebuild parks in urban communities, and do things for kids so they'll be off the streets. And when this career is over, just fade off into the background, have more kids and let them achieve some of their dreams too."

Jennings wasted no time after the release of The Phoenix and returned to the studio to begin working on his third album. He had often remarked in interviews that he had written more than 200 songs over the years he was in prison. The third album, Lyfe Change, was released in April of 2008 and debuted at #2 in Billboard's Top 200 albums. Jennings told Farai Chideya on NPR's News & Notes that the name was chosen to reflect his growth as an artist. "I think your first album is your introduction. Your second album needs to show consistency. And your third album has to show growth in order for you to have a fourth album."

On Lyfe Change, Jennings collaborated with some of the leading performers in hip-hop including T.I., Wyclef Jean, and Snoop Dogg. "Association confirms where you are as an artist," Jennings said to Barhite. In the vein of his previous releases, Jennings continued to compose ballads with serious and inspirational messages. In "It's Real," for example, Jennings spoke about the AIDS epidemic, telling listeners to heed the problems of others when considering their own burdens. Speaking about the song to Chideya, Jennings said, "I think the best any of us can hope to do when we record message-based music is a person might end up in that situation and that song may come back to their mind. And, [regardless] of what people think, some people say that music doesn't stimulate a certain action, I think it does."

With three top-selling albums and aspirations to become more involved in production and artist management, Jennings had become one of the leading figures in the modern R&B community. In interviews he showed no signs of slowing down his production schedule, hinting that he was already working on a fourth album and had several additional projects in the works including a line of retail furniture, a series of children's books, and a new record label distributed through Universal Records. Speaking about the significance of his career and his musical legacy, Jennings told Kenya N. Byrd in Essence, "Honestly, I really don't care if anyone remembers me because I think a great song will outlive the artist…. For me, the greatest form of flattery would be for someone … to remake one of my songs."

Selected works


Lyfe 268-192, Sony Urban Music/Columbia, 2004.

The Phoenix, Sony Urban Music/Columbia, 2006.

Lyfe Change, Columbia, 2008.



Billboard, November 19, 2005; May 3, 2008.

Toledo Blade, May 9, 2003; August 22, 2004; August 20, 2006.

Toledo Free Press, August 2, 2006; May 16, 2008.


"Biography," Lyfe Jennings, 2008, (accessed May 23, 2008).

Byrd, Kenya N., "Lyfe Jennings: Changing the Game,",,16109,1735831,00.html (accessed May 23, 2008).

"Lyfe Jennings Biography," AOL Music, 2008, (accessed May 23, 2008).

"Lyfe Jennings," VH1 Online, 2007, (accessed May 23, 2008).


"Lyfe Jennings Chronicles Personal ‘Change,’" NPR Music, April 29, 2008, (accessed June 20, 2008).

—Micah L. Issitt

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Jennings, Lyfe

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