Jackson, along with a sister and a cousin, was raised by his mother in public housing project on South First Street in Charlottesville.
When Jackson was 2 years old, his father was sent to prison for what would amount to a nearly two-decade sentence.
“It was very, very hard,” Glenis Jackson said. “He didn’t have a father to say, ‘Come on, let’s do this,’ or teach him stuff.”
Jackson began having trouble in school when he was in the fifth grade, with his mother receiving frequent calls about his behavior from the principal.
Glenis Jackson didn’t like the direction things were heading, so she decided to put her career as a licensed nurse on hold and home-school Lester. She did so for the remainder of his education – sixth through 12th grade.
To make the arrangement work, she cleaned houses.
“There wasn’t even a second thought,” recalled Glenis Jackson, who also home-schooled her daughter. “I knew I needed to be able to take care of them and I needed to be able to get to them when they needed me, and that was the best way to do it – by doing domestic housework.”
Under his mother’s watchful eye, Jackson got back on track.
“She was the nucleus of my childhood, my biggest influence,” Jackson said.
Many of Jackson’s fondest memories are of singing around the house with his mother. They often listened to classic soul singers, such as Sam & Dave, who his mom had grown up listening to.