' Lyfe 268-192' was released in August 2004, led by the single 'Must Be Nice' that received heavy spins on radio outlets. Soon he found himself working with the pros to shape his debut album. He wrote some songs for the label, made a cameo in music videos and opened for other artists' concert. He was signed to Columbia Records and soon thereafter nabbed chances in several showbiz events such as concerts and recording sessions. Packed with the determination to step up in the game, Jennings gathered his courage to move to New York City. Executives, concert promoters and even label representatives came looking for him in the hope of getting his signature. His songs 'What Is Love' and 'She Got Kids' received airplays in local radios, thus giving the necessary boost of sale of his EP which then reached more than a thousand copies. He scored five winnings at the gigs show and even received a standing ovation at one point. When he climbed up the stage for the 'Amateurish Night', he was booed by the audience, but as soon as he strummed the guitar and delivered his purpose, the crowd went amazed. Barely a month later he managed to secure a gig at 'Showtime in Harlem' that took place in the prestigious Apollo Theater. The session resulted in a four-tracks EP that he showcased in a local club the next day.

Just one day after his exit, he entered the booth to record several songs that he had penned while in prison. The freedom was not wasted being a wanderer. Ten long years after he first stepped in the prison cell, Jennings smelled the outside air for the first time in December 2002. It was in 1997 when a copy of Erykah Badu's debut album ' Baduizm' got in his hand and became a strong motivator of his career choice. While being incarcerated, Jennings took the most of his serving time by learning to play guitar and consequently write a song. But it was exactly the same place that brought him back to reality and fortunately, also changes to the teen. He was only 14 when he was sentenced for arson and required to go behind the bars in 1992. The plan did not go as smooth as expected for brutality, lacking a father figure and harsh environment led him to a life in prison. The group was short-lived but Jennings continued to pursue a career in music as a solo. In his hometown of Toledo, Ohio he formed a teen singing group consisting of his brother and two cousins and named themselves Dotsons. Born as Chester Jennings on June 3, 1978, he already had a vision of life since his youth. Lyfe Jennings is particularly having 'it'.

A background story that make up the X Factor of an artist is also crucial in building a fan base. The formula to getting it through the music business is not simply possessing a talent and being able to grasp the audience when the music is played.

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