Like OGs in Sunday shoes who know "real music" and the code of the streets, this MC loves to reminisce, recalling forgotten legends and exposing an epic side of Cincinnati Hip Hop that makes non-believers misty eyed and silent.
Off record, though, his story spins wildly. Still, heads listen to his short-stringed sentences to learn what he knows.
After all, people say Holmskillit is the "embodiment of a real MC" because "he's a good host" who can "hold the crowd." His rep says he recorded singles with producers like Hi-Tek, J. Rawls and Usef Dinero and that his hook for Mood's "Cincinnati" stuck in minds as far away as Germany.
And backstage after a recent show, Guru grinned when 'Skillit's freestyle summoned GangStarr's discography.
UndergroundHipHop.com wrote that his 2002 B-side, "Alive," "reaches into the hearts of people who feel depressed" and "injects inspiration."
"I've been sick, so I relate to sick people," Digby says. "That's why I write songs for the sick."
But whispers in the dark about his devil-may-care business approach and skittish tendencies say Digby "does crackish shit," "coulda been the next Hi-Tek" or is a "little bit crazy."
He could tiptoe a tightrope of self defense, but he's thankful for grace and Group Therapy Project, an album of comfort sessions featuring his and Dinero's combined life experiences.
"My mom used to say, 'You spend one half of your life making mistakes, then you spend the other half of your life correcting them,' " he says.
One glaring mistake for even a recording novice is letting royalties slip by. Digby never filed for publisher credit with ASCAP or BMI, so he isn't paid royalties.
"That's one of the key points, having your publishing together," he says. "You make money doing shows, but with publishing you get (royalty checks) quarterly. That's something I'm working on ASAP."
His "biggest mistake," he says, was using cocaine.
"I knew what I was doing, but I was under evil influence," he says, recalling the people around him at the time. "People build you up to tear you down. You might have something going for you, and people can use that to build your pride up and you feel like you can do anything without repercussion, but that's not the case."
Looking back, he's not regretful.
"Sometimes, when God wants to give you a gift, he'll bring you to your knees," he says quietly. "I remember a time when I was laying on the floor with my best clothes on and nothing mattered. I'm an example of the prodigal son."
For Digby, secular and spiritual life overlapped. His parents were Jehovah's Witnesses, yet he remembers walking in after school and catching adults smoking dope.
"A dope fiend in the family, well, everybody has one," he says matter-of-factly. "When you're a kid, you look at everybody as a 'character.' Their life doesn't become real to you until you grow up."
His grandparents sustained his energy with Soul. He sneaked Hip Hop into his collection later. Outdoorsy Oberlin, dance lessons and SCPA became his nests for creativity.
He built a name battling in hallways as "BJ Rock," a B-boy who by 1987 would MC. Socially, though, Withrow High School created Holmskillit.
"Withrow helped me reconnect with the streets," he says, referring to cred he built once he surveyed the scene, breaking bread with Kid Legit, Ruthless Rob (Infinite Evol), Murder Rock, Interphase, The Empire and eventually Three Below Zero (who later became Mood).
"Battling any kid wearing Adidas," he welcomed a challenge.
During his senior year in high school, he "haggled" DJ Icey D for a $50 prize as best rapper. But even at the price of not graduating, Hip Hop felt tangible.
"I got really wrapped up into music," he says. "It got to the point where I had been skipping school a lot. I was just going haywire, going to PrimeTime, staying out all night, smoking weed and drinking."
While studying Islam, he also says he lost touch with his Christian base, namely his family.
He enjoyed the streets' free will, which introduced paranoia. His friend's .38 pistol became his protector.
Digby describes the years surrounding his Hi-Tek/Mood association as "hyper-drive." Having collaborated with Talib Kweli on Doom, Kweli introduced him to Mos Def, who linked him to Rawkus, who heard his demo.
"We were taking trips to New York, doin' shows at Bogart's," he says. "Kweli would come to town, we'd record, then we'd go up there and link with him. I would catch the bus up there broke, and he'd take care of me. I'd have to babysit his fam while he worked at Nkiru Bookstore in New York. We'd go to Nkiru, do shows. I had a demo with Hi-Tek. I was tryin' to get a deal around that time and meeting a lot of people, (but) things didn't work out."
Away from his roots, his spirit broke and he came home to recover. He thought of giving Hip Hop up completely. Ministry called, but a peer warned: "You know you'll be miserable if you do that."
"I just kinda went through having to start over again," Digby says. "Like my mom had to hold me again. I had to go through my baby pictures, refocus and really refine myself."
Today, Digby rekindles his faith as a Witness and hopes to serve a ministry through music, beginning with Group Therapy Project.
"I still have to check myself," he says. "There's an element of charm that goes into what we do that's attractive to others. Along the way, your rep can get flawed, but there's grace. If you work hard, believe and can forgive yourself, then you can move ahead.
"Maybe it wasn't time for Holmskillit then. When He says, 'Pack ya bags, let's go,' then it's my time." ©