Cover photo © 2023 Reed R. Radcliffe

One glance at Oscar Wilson – front man for this year’s Blues Blast Music Award-winning band of the year, the Cash Box Kings — and the way he enthralls the crowd via his deeply personal, easily approachable stage presence and you’d believe the man known as Mr. 43rd Street was born to sing and play the music he adores so much. And you’d almost be right.

The youngest and sole surviving child of H.S. Wilson, a South Side Bluesman, who played mostly on the West Side . He was guitarist and vocalist who played in the style of Lightnin’ Hopkins, Oscar came into the world in the Windy City and is definitely the real deal. But he didn’t start singing professionally until his mid-50s – and only started doing it after a fit of boredom!

Wilson doesn’t know much about his dad because he died two months before he was born in 1953. But because of DNA research and long conversations with his large, extended family, he possesses a much better understanding of his roots than the great majority of the ancestors of former slaves.

“My dad was born in 1905, and I only ran into one person, Henry Gray – Howlin’ Wolf’s old piano player – who remembered him,” Oscar – the last surviving child of nine in the family — told Blues Blast recently. “He came up from Vernon, Ala., and went through both World War I and World War II. My mother didn’t talk much about him and never let me go around his family.

“She was pregnant when he died, and there was whispers goin’ that I was none of his goin’ round. But I finally began to learn more about him by talkin’ to his family in 1971 when I went down to Alabama for family funeral.”

The first of 17 or 18 children in his family, H.S. was born close to the Mississippi border in Alabama while other siblings began life in Jackson, Tenn. – where Wilson’s parents met – and Hickman, Ky. A DNA search revealed that his mom Maxine’s family – with the unusual name Chrisp- all traced back to the Jackson area, where many of his antecedents lived and died in bondage.

On the Wilson side, Oscar’s great-grandparents, Isaac and Rebecca, were North Carolinians who were lovebirds, but were separated when her owner moved her to the cottonfields of Alabama. Desperate, Isaac ran away to join her. Despite living on different plantations in the years that followed, their enduring passion resulted in the huge family Wilson adores today.

“My uncle told me my mom met my daddy when he was comin’ across the hill playin’ his guitar and singin’ ‘I don’t want no woman whose hair ain’t longer than mine,’” Oscar says. “And she said: ‘I’m gonna marry him!’”

Questions about his parentage plagued Oscar until the early ‘90s when he started looking more and more like his dad, found some acceptance and started attending reunions. It was a pain Wilson carried for decades.

And after his dad died, life was hard to the extreme.

“We were poor,” Oscar says. “I would have to run home for tea cakes and powdered milk or biscuits for lunch when I was in school. I had hand-me-down clothes. My mother could make the best somethin’ outta nothin’! She’d buy bushel baskets of peaches, apples or pears…whatever come through…and she’d make homemade preserves. We’d have homemade biscuits and flour gravy every day.

“I like to do songs about eatin’ and food now because I never went to McDonald’s until my sister — who was two years older than me — got a boyfriend. He took us to McDonald’s, I was in heaven. We ate skillet burgers at home, and we couldn’t run to the truck to get ice cream. We ate cheap cereal. When we started gettin’ Kellogg’s when my stepfather came along…oh man, we was raisin’ hell!

“Chicken was our staple. Even today, as long as I got some chicken, I’m happy.”

Oscar grew up on Wells Street just a block south of 43rd Street. It was a booming entertainment district at the time with a tavern on every corner and years before Buddy Guy and a business partner opened the legendary Checkerboard Lounge. Some of the Bluesmen came to my house, Elmore James, Honeyboy Edwards, Little Mack Simmons and Big Smokey Smothers – “my sister had a baby by him,” Oscar says. And many of them would play at the fish fries Maxine hosted to make ends meet.

“That’s where my story began,” Wilson notes. “My mom would have fish fries, and I’d see these people comin’ over. I didn’t know they were this’n that. The one I knew best was Big Smokey. We called him ‘the Ice Cream Man’ ‘cause he had a wagon. He’d bring us treats, and we looked forward to seein’ him.

“My mom was raisin’ us by herself and she wasn’t educated at all. Raisin’ kids was all she knew. We split a six-room apartment with my cousins. They had the front part and we had the back. They had a lot of kids, too, and we all had to share one washroom.

“The stairs were in the front, and they’d come up and be playin’ those box (acoustic) guitars, blowin’ harmonicas and stuff like that. Wasn’t no amplifiers back then. And me, as a little boy, while the other kids would be playin’, I would be standin’ there listenin’. I was attracted to it.

“All of my life, with all of my brothers and sisters bein’ older than I was, I was into doo-wop, R&B, Motown…I came up through all of that. A lot of people pigeon hole me today, thinkin’ I’m just a Muddy Waters/Howlin’ Wolf bluesman. But my favorite blues player was Lightnin’ Hopkins. After my dad died, my mom played him all the time when my pop was on her mind.”

Growing up in that neighborhood, music constantly filled the air. Crowds would gather multiple times a day as someone picked at a guitar or another instrument and played on the street, and house parties were a regular feature, too.

Oscar’s first experience as a singer came at age eight or nine, he says, when he walked to the corner store to get a treat and he heard music emanating from a building on the opposite side of the street. “I crossed the street and Honeyboy – we called him ‘Mr. Honeyman’ – was playin’ a house party. I went over and was standin’ in the door,” Wilson remembers. “He said: ‘Hey, little boy, you like blues?’

“I said: ‘Yessir!’

“’Can you sing the blues?’

“’Yessir!’

“He said: ‘What do you wanna sing?’ and I said: ‘Still a Fool.’ He played it, and I sang it. That’s how it all began. When I was comin’ up, there was always somebody playin’ and I was singin’. And the man would be wonderin’: ‘Hey, little boy, how you do know all these blues?’

“I done forgot more than most people ever know! I could do it all night long. And I was so-o-o good at it, too.”

“In Tilden Tech (high school), one of my brothers, Wolf – his real name was John, was a legend at that school…basketball, football, baseball.

“I went out for football and the coach looked at my application and said: ‘Are you Wolf Wilson’s brother?!? I said yes. You’re gonna play on my team!’ But I got out there and he said: ‘Ah…nah!’ I was a fat boy and wanted a uniform, but I couldn’t play football or basketball for shit. So I joined the band.

“I advanced on baritone so fast durin’ my freshman year, I was in the intermediate band. And by my sophomore year, I was in the concert band. A year later, they recruited me for trombone in the jazz band even though I’d never taken a private lesson. I went: ‘Hell, yeah…’cause you got some nice uniforms.’ And once I got that slide down, I was gone…off to the races!

“It was nice. I was in the marching band, too. Those uniforms got the girls! We had a little bitty ol’ band, but I could never play worth shit even though I was all-city jazz trombone.”

Wilson’s dream was to be a band instructor, something that might have been a possibility because he had scholarship offers from Grambling University, Tennessee State and Florida State, but life simply got in the way. Instead, at his mother’s insistence, he took out loans to attend DeVry University in order to support her with a goal of becoming a TV repairman.

“But she passed that Christmas, and I never went back,” Oscar remembers.

His dream shattered, he spent the next 40 or so years running the street and as a family man, working at whatever job he could find…everything from a barman and bouncer to a maintenance mechanic, from a postal employee – a job he held three times — to mental health worker and more. But it didn’t stop him from sitting in to sing with bands when he finally caught the bug.

That began in the ‘80s, when J.W. Williams – the longtime bass player for the Sons of Blues/Chi-Town Hustlers – invited him to the bandstand at the Cermak Lounge at a time when he was working at a neighboring liquor store. He and his co-workers regularly closed shop and whet there for a drink or two, and they urged him to do it.

“J.W. let me sing a song I even do now, B.B. King’s ‘Just a Dream,’” Wilson remembers. “That was that. And then I started goin’ with this girl whose brother was Bassman Pete (Peterson), who was playin’ with Johnny B. Moore and other folks around town. Bassman Pete and Johnny would come over to my house to practice…and Johnny – oh, man, he was a great guitarist — and I would mess around doin’ some Lightnin’ Hopkins and stuff like that.

“Then Johnny would come by and say: ‘Hey, Hank – my nickname…a lot of folks call me that, do you know that new Johnnie Taylor song? Would you come out and do it with us tonight?’ I’d be like: ‘Yeah, okay…’

“At that point, I did it to just have some fun, and folks would tell me: ‘Hey man, you’re in the wrong business.’ I’d do a song here and there, and then Melvin Taylor – another great guitarist — comes along, and I’d do ‘Cadillac Assembly Line’ and some Jimi Hendrix and Albert King with him.

“Most folks don’t know it because the Cash Box Kings do mostly ‘50s, ‘60s and ‘70s-style blues, but I’ve only revealed the tip of the iceberg of what I know and can sing. With the Kings, I’m just the side show. I just show up and they tell me what to do. I don’t control what’s in our sets or what goes in or off our albums.

“But Joe Nosek (the Kings’ harp player and co-founder) is my friend and his kids are my godsons. I love ‘em. It’s his band and he gets to call what goes down.”

Wilson’s professional singing career actually began in the 2000s after he’d moved to Janesville, Wis., a town of 60,000 in the south-central part of the state — in order to provide a safer environment and better education for his youngest, high-school age daughters, a place where they could take part in art and dance programs they wouldn’t have been able to join in Chitown. An older son was already living and working in Madison, a short drive to the north, told me to move up there because it was the land of milk and honey. Lmao.

The girls eventually graduated and moved back to the Windy City shortly thereafter, leaving Oscar – who was working in a mental health facility at the time – behind to fend for himself.

“I was sittin’ at the crib one night, and I read the Janesville Gazette newspaper,” Oscar recalls. “It said: ‘Blues jam at the VFW Monday night…James Tate and the 008 Band/Cash Box Kings.’ I went up there. And of all the people that was there, this guitar player came over to me and said: ‘My name’s Travis Koopman of the Cash Box Kings. This is half my jam here, do you play?’

“I said: ‘Yeah. I sing and play a little harmonica…’

“’You wanna come up?’

“’Yeah. No problem.’

“I went up there, and we slayed it…knocked ‘em off their feet, man! He said: ‘Come back next week.’ I did and…the same action. He said: ‘Hey, man, whatcha wanna do?’

“I said: ‘I’d like to play at Buddy Guy’s Legends in Chicago…back home.’

“’Okay,’ he said. ‘Give me a couple of weeks…we’re gonna be there. Meet us there.’”

The time passed quickly, and as promised, Koopman invited him to the stage. Wilson sang three songs that night, and each of them received a standing ovation. Oscar’s been a regular presence in the Kings’ lineup ever since.

“It must have been divine intervention or somethin’,” he says, “’cause I wasn’t lookin’ to be in no band. I was just bored. Sometimes Joe makes it sound simple, but I don’t think it really was. I don’t think we really hit it off at first ‘cause he, Travis and (drummer) Kenny (“Beedy Eyes” Smith) had been doin’ all the singin’, and then they had me, too.

“But then Travis left for the Cayman Islands. He’s a union plumber, and he started workin’ down there. Then Joel Paterson joined The Cashbox Kings, Joel opened up stuff for me that I didn’t know I had, too. He got me into a Percy Mayfield style or somethin’ like that. And Sunnyland Slim, too.

“I never knew how important he was. They’d bring me the songs, and I’d learn ‘em. I didn’t get to meet Sunnyland and all them people. The people I did meet, I met when I was little. And when I was an adult and Sunnyland and all the others were up on the North Side, I wasn’t into it like that. Durin’ that time, I was discoin’, I was dancin’ all night long!

“I think things happen when they’re supposed to. Back then, I was drinkin’ too much, for sure, and nobody couldn’t tell me nothin’. I was havin’ too much fun. I’m a lot more mature now. And I love this business, man!”

Wilson’s first recording with the Kings — Cuttin’ Heads: Live at the Cuda Café — came about six months after he joined the lineup. “Man, that was a fantastic night, and a shaky night,” Oscar admits. “I was shakin’ like a dog shittin’ Persimmon Seeds ‘cause I thought I was gonna mess up.

“I knew the lights was on me now. But I did okay. And when I heard the songs, I was like: ‘Wow, that’s me!’ It was awesome, man.

“And then the one we did after that…I-94 Blues, I know that (current guitarist) Billy Flynn didn’t write ‘Tried So Hard’ for me, but I love him for it ‘cause I was goin’ through the same shit the song was about at the time – my woman walkin’ out. I did that song straight from my heart.

“And as I’ve gone on, I’ve noticed I’m really gettin’ better and better. I feel the progression.”

Wilson’s been a key cog in the six releases that have followed on Blue Midnight, Blue Bella, Blind Pig and Alligator, most recently Oscar’s Motel. He’s also manage to squeeze in a solo CD, too, One Room Blues, which appeared on Sunnyland’s old label, Airway, in 2017 when the Cash Box Kings were on break and between recording deals.

Co-produced by Sam Burchhardt, Slim’s longtime sax player, and Joel Paterson, who lays down sensational guitar and is one of several talents who’ve held down six-string duties in the Kings, it was conceived to support Oscar’s trip to Lucerne, Switzerland – his first-ever European appearance. It delivers a taste of Wilson’s other influences, which span jazz and blues.

Although he’s never thought of himself as a songwriter, Wilson’s really honed his talent in that area, something that’s come to the fore in recent Cash Box Kings albums – both with solo creations and in partnership with Nosek.

“My Mom and Dad’s blues was different than mine,” he notes. “I’ll put out somethin’ like ‘Blacktoppin’’ was about bein’ down in West Lafayette, Ind., and they had them old bobtail dresses and it was mostly young white guys and girls, and I was the only black guy. After we finished, they were askin’ what I was gonna do after the show, and I said: ‘Man, I’m figurin’ to go blacktoppin’’…and I went and wrote it. I put in there some things that actually happened when I was in high school about goin’ across the tracks.

“’Bluesman Next Door’ dealt with prejudice and was true, sayin’ you can dig me on stage but it doesn’t mean you want me bein’ your neighbor. ‘If You Got a Jealous Woman, Facebook Ain’t Your Friend’ says it all. And ‘Move Out to the Suburbs’ was about 43rd Street the way it used to be.

“If you go there now, it’s not the same. We used to walk everywhere we’d go. It was long before the Checkerboard Lounge opened…Theresa’s Lounge, Florence’s, all over the city. There wasn’t no drivin’. Walkin’ and talkin’, and the next thing you know, you’re there.”

And your skin color didn’t matter. At some of the joints, the moment you stepped out into the dark of night in those neighborhoods, you could be putting your life in your own hands because of the possible dangers.

“Gentrification has changed everything…high-end housin’, Starbucks and all that stuff,” Oscar notes. “I went over east by Muddy’s house no too long ago and I thought I’d gone into the Twilight Zone.”

Real-life people and images frequently appear in Wilson’s lyrics in such songs as “Down on the South Side” – which describes many of the folks who used to populate the taverns in the neighborhood, and downhome philosophy appears in numbers like “Ain’t No Fun (When the Rabbit’s Got the Gun).”

The band’s latest effort, Oscar’s Motel, is a somewhat of a departure for the band in that it’s far less political than some of their previous releases. Written during the pandemic – often via Zoom, it delivers upbeat, good-time messages along with material that’s a whole lot of fun, especially “I Can’t Stand You,” Wilson’s make-believe feud with vocalist Deitra Farr, who shares the mic on the tune.

“That started when I first met her,” Oscar says. “I have to give a lot of credit to Billy, and he introduced me to a lot of people. He introduced me to (harp player) Mark Hummel, telling him: ‘This is Oscar…he’s a human jukebox.’ And Mark invited me to go on a little tour with Deitra, Billy and an all-star cast.

“When I met her, she was feisty, and I was goin’ ‘yes, ma’am, yes, ma’am, yes, ma’am.’ We really hit it off. But during the pandemic, she started sayin’ on the internet ‘I can’t stand you!’ And I started sayin’ ‘I can’t stand you either!’ And people started laughin’ and lookin’ forward to us sayin’ somethin’ every day.

“And she’s such a computer-magic person that she’d just jam me up every time, make a billboard or find some pictures side-eyin’ at me. And people looked forward to that soap opera. She’s so-o-o funny, man! All my brothers and sisters are gone, but she acts like my sister, Bebe.

“We did that song on one take, and everybody loves it.”

What’s next?

“I dunno,” Wilson admits. “Like I say: I dunno what’s gonna happen ‘til it happens. We have other songs, and Bruce (Iglauer, Alligator’s owner) says we’re gonna do another album. But I’m always the last to know.”

Meanwhile, he remains frustrated that the Cash Box Kings aren’t getting the bookings they deserve for big festivals and events. “It totally irks me right now that they’ll have a ‘blues’ festival and no blues on it,” Oscar says. “Or if they do, it’s most often someone who’s more of a rocker. You can get a guy who’s playin’ all of them damn notes, and he does all of that for what now?

“Or you can get a two-string playin’ motherfucker, and he’d kill it.

“The blues is a feelin’ and it touches somebody’s heart. Minor blues, slow blues…that’s what I’m all about…cryin’ in your beer…or happy…’cause the same song that’ll make you cry can make you happy, too ‘cause it can bring back a memory or somethin’…like ‘C’mon in This House,’ which reminds me of my mother.

“When she was playin’ that song, we knew we’d either be gettin’ our Zoom-Zooms and Wham-Whams (candies) and watchin’ ‘Thrillerama’ on TV or some blood would flow ‘cause there was gonna be a fight.

“I want you to leave my performances knowin’ that I’ve touched your heart and touched your soul while tellin’ you what’s happenin’ with me at that time. I’m not a verbatim guy. I may do the same song, but it wouldn’t come out the same way. I give 110 per cent every night, but I don’t feel the same way every time, and people in the audience don’t feel the same way either.

“I’m just a bluesman in my heart and soul. It’s somethin’ that can’t be explained. You’ve got to know it.”

And one thing that Oscar wants everyone to know is that “I love my fans for stickin’ with me through the good times and when times were bad. And I love my job!”

Check out Oscar Wilson and the Cash Box Kings’ music by visiting their website, www.cashboxkings.com, and find out where they’ll be playing next. You’ll be glad you did!