7 minute read

Lyfe Biography

Sang in Family Group, Auditioned from Prison, Produced Own Album, Selected discography


Singer, songwriter

Lyfe, photograph. Frederick M. Brown/Getty Images.

Toledo, Ohio-born singer and songwriter Lyfe has a sound that is all his own. The many attempts that have been made to label it show just how unusual it is: they range from folk-rap (Lyfe's own contribution) to singer-songwriter (Seattle Times) to R&B/hip-hop/folk (Billboard). Lyfe writes honest, emotional songs, drawn on his own experiences. He plays an acoustic guitar, an instrument he learned in prison. And Lyfe's musical style, like that of the philosophical vocalist Erykah Badu, hovers between hip-hop and R&B, with classically soulful vocals framed and interspersed by spoken interludes or brought up short by hip-hop's abruptness and humor. After releasing his debut album, Lyfe 268-192, in 2004, he gradually but steadily gained a large fan base.

Sang in Family Group

Lyfe was born Chester Jennings in Toledo, Ohio, around 1976. He took the name "Lyfe" after he was released from prison and began a career writing songs, he said, about life's trials. The spelling, according to Toledo Blade article, indicated that his music often asks the question "why?" His first musical experiences came in church, and several members of his family went into musical careers. His brother Jay joined a group called Lade Bac that was featured on an album by R&B star Keith Sweat, and an uncle, Keith Dotson, formed a family group called the Dotsons that Lyfe joined when he was ten.

The Dotsons tried to follow in the footsteps of the phenomenally successful sibling ensemble New Edition; they scored several talent-show wins and got as far as making a demo recording. The group broke up after that, but local producers had already identified Lyfe's voice as something special and encouraged him to work toward becoming a solo act. However, he began to drift away from his studies at Toledo's DeVilbiss High School. "I ran around, did a lot of nonsense, got in a lot of trouble," he told Corey Moore of National Public Radio. At 16, he was sent to prison for ten years on an arson charge.

Lyfe made use of his time behind bars by working on his music. He joined a prison gospel group and also learned to play the acoustic guitar, one of the few instruments available to him. "One of the hardest parts was that people kept on telling me to shut up," Lyfe told the Baton Rouge Advocate. "It wasn't like there was somebody there teaching me to play, so it was really hands-on training and a lot of bad notes. Everybody was, like, upset." After a while, Lyfe won over the other prisoners, some of whom were musicians themselves. "I definitely got some tips from some guys that was in [prison]," he told Associated Press writer Raqiyah Mays in an interview reproduced in America's Intelligence Wire. "Like, I'd get a chord here, and a chord there, just write a whole song off that one chord, [based on] the whole mood of the chord." He was also inspired by Erykah Badu's Baduizm album, a copy of which he had in his cell.

Auditioned from Prison

As he approached his prison release date at the end of 2002, Lyfe talked prison administrators into letting him make videos of performances he gave for other prisoners. He sent those tapes as an audition to the Showtime in Harlem television talent show, and two days before he was released he got word that he had been accepted. Lyfe hit the ground running after his release. On his second day out of prison he recorded a demo, and on the third day he performed in a club. His Showtime in Harlem debut came in January of 2003. He was booed at first when he walked on stage with an acoustic guitar in the middle of a set of hip-hop performers, but he got a standing ovation (for the song "Cry") his first night out and ended up winning the competition five times. His four-song demo evolved into an extended-play CD called What Is Love? and he began to garner sales and airplay as he drove as far as Louisville, Kentucky, from his Toledo home base, playing his guitar and selling his EP at car washes, salons, and anywhere else he could set up a stage.

The buzz that built around Lyfe's music began to attract music-industry figures, and he garnered promotional support from a Budweiser beer distributor and appeared at an NAACP convention. The sister of one of his fellow prisoners became his manager. Finally, Lyfe made the move to New York City, settling in Brooklyn and soon landing an opening-act slot for hip-hop star Nelly at Radio City Music Hall. Late in 2003 he pitched his music to Sony Music Label Group U.S. president Don Ienner, who signed him to the label after hearing three songs. Only ten months earlier, he had been behind bars.

It took a while for Sony to realize the unique nature of Lyfe's talent. He wasn't a rapper, but, despite his lush old-school vocals, he did not fit the stereotype of the romantic neo-R&B vocalist either; his music had a raw, honest quality that diverged from the sexy fantasy world of a performer like D'Angelo. "I had a lot of people from the label, like 'You gotta do this and that and appeal to women,'" he recalled to Mays. "And I'm like, the truth is going to appeal to women more so than [sic] I'm gonna appeal to them. Because the truth will last longer." Lyfe cultivated an informal urban look, with baggy jeans, T-shirts, and Timberland boots. "I don't own a suit. I don't own hard shoes. I don't own a shirt with a collar," he told Mays.

Produced Own Album

At first, Sony paired him with members of its stable of R&B producers, but the results weren't satisfactory. Lyfe asked the label to let him produce his own album, something virtually unheard-of for a new and unknown artist. Label executives agreed but gave him very little time to work. For Lyfe, who had been working on his music for years, that wasn't a problem. Lyfe's debut album, Lyfe 268-192, was released on August 17, 2004. Billboard called it "an anti-bling album that definitely goes against the contemporary grain. No brand-name producers contributing hot beats, no big-name guest cameos."

The album's title referred to the number he was given in prison, but he rarely talked about his prison experiences, much less boasted about them, and Lyfe's music in general reflected a familiarity with street life but a refusal to glamorize it. "I'm from the streets and I'm writing for the street cats," he explained to Rhonda B. Sewell of the Toledo Blade. "I want to tailor my message for people in the streets so they can take something away from my music." "Must be nice / Having someone who understands that a thug has feelings too," Lyfe sang in the breakout single "Must Be Nice."

At a Glance …

Born c. 1976 in Toledo, OH; moved to Brooklyn, NY, 2003. Education: Attended DeVilbiss High School, Toledo.

Career: Singer, 2003–; signed to Sony label, 2003.

Addresses: Label—Sony BMG, 550 Madison Ave., New York, NY 10022. Web—www.2lyfe.com.

Lyfe 268-192 built slowly, but "Must Be Nice" cracked the pop top 40 and the Billboard magazine Hot R&B/Hip-Hop Singles & Tracks top five. Thanks to constant touring, much of it as an opening act for R&B vocalist and acoustic pianist John Legend, the album gained strong word of mouth, and Lyfe was able to celebrate a gold record for sales of 500,000 copies in the summer of 2005 even though a second single hadn't been released. By the end of the year he was closing in on a million, aided by the release of a second single, "Hypothetically," which was remixed to include a guest appearance by American Idol winner Fantasia. "This is the quietest million I've ever sold as a record executive," Sony Urban Music vice president Lisa Ellis told Gail Mitchell of Billboard.

Appearing on television's Jimmy Kimmel Show in November of 2005 and touring as a headliner with fellow Sony artists Vivian Green and Goapele, Lyfe was not at a loss for how to sustain his growing momentum. He had written more than 200 songs. He had already completed a set of four children's books called The Adventures of Lyfe, with animals or other embodiments of life itself as characters in the books, and he was pitching a film script. As he planned to return to the studio to work on his sophomore release, Lyfe seemed one of urban music's brightest and most original prospects.

Selected discography

What Is Love? (self-distributed EP), 2003.
Lyfe 268-192 (includes "Must Be Nice" and "Hypothetically"), Sony, 2004.



Advocate (Baton Rouge, LA), October 22, 2004, p. 10.

America's Intelligence Wire, July 29, 2005.

Blade (Toledo, OH), May 9, 2003; August 22, 2004; December 10, 2004; July 28, 2005.

Billboard, November 19, 2005, p. 30.

Chicago Sun-Times, December 2, 2005, p. NC7.

Seattle Times, August 29, 2005, p. E1.


Lyfe, www.2lyfe.com (January 5, 2006).

"Lyfe," All Music, www.allmusic.com (January 5, 2006).


Interview with Lyfe by Corey Moore, News & Notes with Ed Gordon, National Public Radio, June 29, 2005.

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