R&B singer/songwriter/musician Chester Jermaine Jennings has lived the popular cliché “been there, done that.”
Jennings, known professionally as Lyfe Jennings, will headline E.J. Thomas Hall at the University of Akron on Friday, with an all-Ohio bill featuring Cleveland neo-soul songstress Conya Doss, Cleveland Heights singer/songwriter Antoine Dunn and Akron artist Damon Leon.
While many of his counterparts invent their rap sheets, Jennings has one that is all too real.
In 1992 at the age of 19, Jennings, a Toledo native, went to prison for a decade for arson. While incarcerated, Jennings, who grew up singing in church and had a music group with some relatives as a teen, reconnected with his God and his music, drawing heavy inspiration from Erykah Badu.
Upon his release Jennings quickly recorded a demo CD and made his way to New York City, where he competed on the historically unforgiving stage at Harlem’s Apollo Theatre. Jennings was initially booed simply for having a guitar strapped to his back (and stepping onstage), but quickly won the crowd over with his rough, slightly nasal tenor and honest singing. He went on to win Showtime at the Apollo five times in a row.
Two years later he released his debut album, Lyfe 268-192, the numbers he was assigned while a ward of the state. Musically, the album was fairly standard contemporary R&B with welcome splashes of real guitar and other analog instruments, but what set it apart was his lyrical honesty and plainspoken, often first-person, always vivid narratives of real life, found in tunes such as the baby-mama drama song Greedy: “Like it’s my fault that she got on welfare / I told her we can go half on the Similac and the daycare / But no, she got comfortable at the bottom and wanted to stay there.”
On his second album, 2006’s The Phoenix, Jennings went even deeper into his life experience, offering spoken intros to nearly every song and having a No. 1 R&B hit with S.E.X., on which he and guest singer LaLa Brown advise a young girl growing up too fast not to give herself to the first guy whispering empty promises in her ear. The album hit No. 2 on the Billboard 200 chart and Jennings was hailed by critics and R&B fans as a socially conscious singer/songwriter, telling it like it is.
The streak continued on Lyfe Change, a more upbeat collection made with outside production help, but still uniquely Lyfe, with songs about the vagaries of fame, growing up and other topics that seldom make it to “blazing hip-hop and R&B radio.”
All seemed right in his world until a 2008 altercation with the mother of three of his children (he has three boys and a girl) involving a gun led to a police chase, landing him back in prison for another three-plus years.
During that second stint, he released his fourth album I Still Believe in 2010, showing that musically he was at the top of his game. It was another Top 5 R&B and Top 10 album, with hits including Statistics, a skeletal ballad using percentages to help ladies (a huge part of his audience) understand why a good man is so hard to find: “15 percent of all men got a complex / 15 percent of all men don’t practice safe sex / 20 percent of them come from homes without a father / So there’s a 50-50 chance that you’ll marry a coward,” he sings.
Released from prison in early 2012, Jennings has taken his time coming back, performing spot dates with other artists (including his hero Badu) and at festivals, where he found his audience eager for his return.
“It feels good. Music is so fickle and it changes, so that you actually wonder what your reception is going to be, so it was definitely a great thing for me,” Jennings said by phone while walking with sons Elijah and Phoenix.
Last month Jennings released a new single, Boomerang, another plain-spoken tale of what can happen to a man when he does his woman wrong. And lest folks think Jennings doesn’t understand irony, it was not happenstance that Boomerang was the first single.
“Well, with my situation and now coming home, we just thought it was a very relevant song to my life, and personally I try to keep it as close to my life as I can,” he said.
While he has had a successful career, there is always the nagging notion that he could be a crossover smash if he just wrote a few more strip-club-ready songs about partying and/or his sexual prowess, and spent a bit more of his album budget on getting verses from the hot emcees of the moment. But Jennings knows better.
“I hear that sometimes. But one thing for sure is that everybody is going to gravitate back to the truth,” he said.
“That stuff is cool, but it’s fly-by-night. Yeah, you’ll have a hit record but a year or two later you can’t even tour. But no matter how much radio presence you have, or strip club presence you have, that doesn’t necessarily mean you have a career. So I keep on writing for a career,” he said.
Jennings’ career and life certainly seem to be back on track. Aside from his freedom and the new single making its way onto radio, he was approached by VH1 to be the subject of a reality show to be called Our Lyfe, which began shooting last week and may hit airwaves in the fall.
“Chaos. Just chaos,” Jennings said of the shoot. “It’s extremely weird and extremely stressful because I’m not a drama kind of guy. Definitely these days I try to stay out of drama’s way. It’s being shot with my three children’s mother [ex-manager Joy Bounds] and those guys are characters.”
Last week Jennings turned 40, and though now he says he doesn’t think about it much, when pressed he does admit there was a time in his life when turning 40 seemed as likely as turning 140. Now he says he’s just trying to keep looking and moving forward.
“Yeah, where I grew up it was hell making to 30, let alone 40. So I’m blessed and try to dwell on those blessings, because I think you get more blessings when you focus on those than when you focus on the negative.”
Porch Rokr rocked
I spent a few hours walking the route for the first Highland Square Porch Rokr Festival on Saturday, and I have to say it was pretty awesome. I’m sure folks have their nitpicks — such as a few canceled shows — but hopefully constructive feedback (as opposed to whining and yelling) will make next year’s festival even better.
I saw a few thousand folks of all ages, backgrounds and groupings wandering Highland Square, going from porch to porch, checking out the impressive variety of locally grown talent (though the lone hip-hop act, Trackblazas, unfortunately canceled their late performance). Neighborhood denizens cleaned out their attics with yard sales, kids sold pop and lemonade on their front lawns, and reasonably friendly Akron police officers made their presence known without making it unnecessarily felt.
I saw The Bizzarros (“Original Akron Music Since 1976!”) play a hot set to a packed lawn, and got my first glimpse of the intriguing ladies of Light of the Loon, their dark piano-driven indie cabaret tunes laced with a smart, macabre sense of humor (“Whatever we do, we’re all gonna die,” went the chorus of one song).
I saw the fun, acoustic “sardonic string band” the Cuyahoga Valley Frackers draw random folks off the street to their porch (“Oh, look honey, they have banjos, that sounds interesting,” the better half of an older couple walking behind me said before they headed toward the music.) The young trio Assassin Broadcast got some toes tapping with their tuneful, vaguely proggy indie rock, and the Bleeding Feathers wrapped up the day with their grooving “rusty barn rock blues.”
A Highland Square Neighborhood Association official told me they sold out of Square Cards, the fundraising component of the festival, and by all accounts the event was an unqualified success.
Kudos to the association, participating bands, artists, vendors, neighbors, porch hosts and all the folks who came through Highland Square and enjoyed themselves without incident and without leaving garbage all over the neighborhood.