Lester Jenkins, musically known as Lester Jay, grew up in Bellwood, IL, a small suburb outside of Chicago. At the tender age of five, Lester Jay began singing at New Horizon Missionary Baptist Church in Chicago, IL where his late father Lester Jenkins Sr. was an associate pastor, and his mother was choir director. From this upbringing Jay’s passion for music was realized, and a star was born. 

Gospel music consumed Lester Jay’s early musical interests until a pivotal moment in high school when a classmate introduced him to the art of secular music. In 2002 Jay was introduced to small indie label ILL Entertainment in Melrose Park, IL. 

“I never thought I'd be so intimately associated with the Chicago rap scene, so the opportunity was amazing. ILL Ent wasn’t a major label, but they carried themselves like they were. My first experience with the label was something out of a reality show; the owner had something of an initiation process and I had to prove myself. He asked the producer to play a beat and I had to freestyle sing over it like a rapper, off the top of my head. and I did it, and I became part of the label.” -Lester Jay 

Lester Jay’s melodic freestyle was so well received by the label that it earned placement on ILL Entertainment’s mixtape “Any Nigga Can Get It" Volume One and Two. Once Jay was officially part of the label, music became his life. Initially, he and the label’s other songstress Ashley B recorded hooks for other rap artists and with each song recorded, Lester Jay’s passion for music grew deeper. He spent so many countless hours after school recording that he literally began waiting for the label’s in-house producer to finish tracks everyday. Lester Jay began discovering his “studio voice” and was ready to record to his own project. In 2004 Jay released his first solo project entitled “The Motions,” however ILL Entertainment dissipated before it ever had its chance. 

In 2005 Lester Jay began attending Columbia College Chicago and his journey continued. While at Columbia, Jay learned the fundamental principles of live music, being in a band, booking shows and live performances. Some of his most noteworthy performances occurred while he was in “The Down and Dirty Blues Band,” a student-band comprised of the best performers from a blues class Jay attended. Jay performed at a myriad of events and venues including Buddy Guy’s, Navy Pier, Chicago’s Blues Fest, House of Blues, and the Donald Lawrence showcase of the Arts 2007. Jay was also apart of various projects and television appearances including American Idol, UK Verizon promotion for singer/songwriters but his personal favorites are more intimate venues where he can reach out and touch his audience.

In 2011, Lester Jay released his first duo project with hip hop artist and producer Tonestyles at the Tantrik, Chicago, entitled "My Moment.... A BBM production". In conjunction with the Midwest Pocket Record Pool tour & Urban Grind TV in 2011 and 2012, Jay was able to promote and perform songs from that album at various places across the Midwest from Missouri, Illinois and Indiana, including the esteemed Hustle & Joe's Sports Bar owned and operated by the late Joe Jackson. https://youtu.be/4lj2i0GQUgo

In 2013, Lester Jay released his first solo project entitled "The FreeDum Project" at the infamous Reggies Rock Club in Chicago, IL. Having complete creative control over this project and release concert, Jay was able to give a glimpse of a dramatic stage show and visual content that was quite different from his prior projets https://youtu.be/DXgqaQdAL1c. With this project Jay was able to continue to tour across the Midwest and perform at a few club sites and festivals including Kankakee's Merchant Street Music Festival. https://youtu.be/XzzFcEXuHM0

Through 2013 - current Lester Jay has found a new genre in which to express himself in House/Dance, and has done so all while being able to find his queer authenticity. Along with the array of collaborations Lester has the privilege to engage in (with production from England, South Africa, and here in the states in Colorado, California, Atlanta, and his home state of Illinois), Jay is lending his talents to the "Tear Dry on their Own, a tribute to Amy Winehouse" tour, as he continues to grace Chicago stages, including most recently (before the pandemic) the Cubby Bear https://youtu.be/uCtYsa3IAEU, and post-pandemic finding a home in queer artistic spaces like the Black Queer Pride by Lighthouse Foundation of Chicagoland and Lakewood's Porchfest 2021 https://www.instagram.com/p/CPzR-HaAS5x/?utm_source=ig_web_copy_link.