Lyfe Jennings began singing in church. But after getting caught up with the wrong crowd, he found himself serving a lengthy sentence behind bars. After discovering a popular neo-soul artist while locked up, he decided to pursue a singing career. Sadly, his untraditional journey to the top included numerous setbacks. Lyfe ventured away from the straight and narrow and paid the cost by seeing his music career quickly fade away.
Here’s what really happened to Lyfe Jennings.
A life-changing decision
Chester “Lyfe” Jennings was born on June 3, 1978, in Toledo, Ohio. After losing his father at a young age, he found solace singing in the church. As a teenager, he started a group called The Dotsons, with his brothers and cousins. Before the group could make an impact on the industry, they broke up. Lyfe headed to the streets and started running with the wrong crowd. That led to him making a decision that would change everything.
At the age of 14, Lyfe accompanied a group of friends to a house to seek revenge against a rival dealer. One of the men threw a firebomb inside the house, taking the life of a 25-year-old mother of six.
Lyfe and his friends later realized they hit the wrong target, but it was too late. They got locked up on charges. His lawyer argued that Lyfe had no idea about the plan to strike the house and thought he was only tagging along to vandalize a car. The court didn’t buy it, and he was found guilty of arson and was sentenced to 10 years behind bars.
The Badu Effect
In 1997, while he was still finishing out his sentence, Erykah Badu’s debut album Baduizm found its way inside Lyfe’s jail cell. He told the Clayton Perry website that listening to the neo-soul artist changed his perspective on music.
He began working on music every single day and joined the prison’s church band. He learned how to play the guitar, since that was the only instrument allowed behind bars. Here he adopted the moniker, “Music for Lyfe.” His friends behind bars thought the name was too long, so he went with the name Lyfe instead.
It’s showtime
A slow climb
Feeling confident about his victory, he moved to New York City to pursue a record deal. He signed with Columbia Records and his debut album, “Lyfe two six eight–one nine two” — which paid homage to the identification number he was given while incarcerated — was released in August 2004.
Even though the song “Must Be Nice” was a radio favorite, the album had a slow climb to the top of the charts. Lyfe told Vlad TV he still had money left from his record deal advancement to help get him by. So he decided to go on tour and perform for free. Those free concerts helped him gain notoriety. His label started to believe in him, so they put more and more money behind him.
Nine months after the album’s release, it peaked at number one on the Billboard top R&B/Hip-Hop chart. The album was then reissued in 2005 with a new version of the song “Hypothetically” featuring American Idol winner Fantasia. To Lyfe’s amazement, his album was certified platinum a year after its initial debut.
A second album & tragedy
According to All Hip Hop, Lyfe and his then-girlfriend and manager, Joy Bounds, welcomed a son named Phoenix, and, in 2006, he released his second album named after his new bundle of joy. The album included the song S.E.X. featuring singer Yolanda “La-La” Brown. The song peaked at number three on the charts.
Lyfe reportedly asked La-La to join him on the road. But after a year of performing together, they reportedly got into an argument and she was kicked off the tour. She returned to her hometown in Milwaukee and linked up with a producer to kick start her solo career.
In 2007, Lyfe’s girlfriend Joy gave birth to their second child Elijah. And then some sad news. La-La and her producer were found riddled with gunshot wounds inside a bedroom above a Milwaukee recording studio.
More trouble with the law
In 2008, things were not going well with his record label. Lyfe told the Clayton Perry website he felt like the label was trying to turn him into a cartoon. He clarified it by saying they tried to get him to push out the best-selling narrative, instead of allowing him to make music that would change lives. He left the label behind and signed a new record deal with Warner Brothers. That same year, he reportedly fathered a daughter with another woman and released his third album Lyfe Change — an ominous title that foreshadowed a major shift.
The album debuted at number four on the Billboard 200 chart and sold 80,000 copies in its first week. Instead of celebrating its success, an Atlanta newspaper reported Lyfe was involved in an argument with Joy. He followed her to her family’s home in an Atlanta suburb, destroyed the front door, and fired shots in the street.
When cops arrived, Lyfe led them on a 90 mile-per-hour chase that ended when he crashed his Corvette. In response to the charges, Lyfe later told Power 105.1 radio station that he acted out of anger and was in his feelings about his children. He added, “Females play games about your kids and I don’t really play about mine.”
While out on bail, he made good use of his time by releasing his fourth album, I Still Believe, in August 2010. Lyfe announced to his fans that the album — which featured Fabolous, Bobby Valentino, Ludacris, and Anthony Hamilton — would be his last.
He got engaged to a woman named Marquita Goings, and they announced they were expecting a baby. He signed up to go on tour with Anthony Hamilton, but first, he had to face the court to address the altercation he had with his ex Joy, two years prior.
In September 2010, he pled guilty to driving under the influence, fleeing the police, and possession of a weapon by a felon. According to Billboard, Lyfe asked the judge if he could go home and say goodbye to his children. His request was denied and he was hauled off to serve a three-and-a-half-year sentence.
Anthony Hamilton and Lyfe’s label didn’t even know he was locked up until the singer posted a since-deleted statement on his Facebook page. At the time, Lyfe had no idea how many bridges he was burning.
Starting over
In February 2011, Marquita gave birth to Lyfe’s fourth child, Lyfe Michael Jennings. Unfortunately, while behind bars, he received a call from Warner Brothers record label letting him know he was dropped from the label.
In 2013, Lyfe was released. He told Vlad TV all of his money was gone because he spent it on child support, mortgages, and taking care of people in his inner circle. He thought he would be able to pick up right where he left off, but no one wanted to deal with him. Music executives were too afraid to invest in him over the fear that he might get locked up again.
Lyfe moved in with his girlfriend before hitting the road to perform at various venues. Instead of making $20,000 per show, like he did prior to getting locked up, he was only getting paid three to four thousand dollars per show. He thought his career was over until he received a call from Mass Appeal records signing him to a new record deal. He released his fifth album called Lucid. A sixth album entitled Tree of Lyfe followed in 2015. The album peaked at number 9, proving that Lyfe was still a major player in the music industry.
A girlfriend, a wife & more babies
In 2016, he pursued other avenues when he appeared on the reality show Love & Hip Hop Atlanta as Karlie Redd’s love interest. Lyfe pretended to propose to her on the show, only to dump her right in front of the cameras. He told the Situations with Wanda Smith radio show he didn’t think Karlie would be a good role model for his children. The truth was actually much crazier than anyone could have imagined. He and a woman named Gwendolyn Scharkowski reportedly got married two months before he appeared on LHHATL.
His life began to unravel from there. In 2016, he welcomed a son named Iam with his wife Gwendolyn (pictured, above), and a child named Knoah with a woman named Indiya Mendoza. Later that same year, his first baby mama Joy received a temporary restraining order which required Lyfe to stay at least 200 yards away from her and their two sons. Furthermore, in February 2017, Gwendolyn filed for divorce citing infidelity.
In 2018, he welcomed his seventh child. And on Valentine’s Day, 2019, he accused one of his women of putting her hands on him.
Is he ready to retire?
On a happier note, he released a new album entitled 777 in August 2019. According to Rated R&B website, he’s now ready to officially step away from the industry for good. He said, “This is a task that requires soul-searching and the audacity to vocalize one’s mistakes. I believe I’ve done that, honestly, over the past decade.”
Lyfe told the Clayton Perry website that looking back on his career, one thing he regrets is not taking full control of his projects. He always had the desire to work on bigger and better things, but his labels always held him back.
When asked about the legacy he wants to leave behind Lyfe said, “I just want my legacy to be that I made a difference.”
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