Oscar Wilson’s resume checks off a lot of boxes.

First-and-foremost, he’s a charismatic frontman. Most would agree that at 6-3, 300-pounds, he looks larger than life stationed up on the bandstand.

He’s also a talented songwriter, a well-respected harp blower and just an all-around hard-working and extremely nice guy.

But as he found out recently, there’s one skill that is most definitely lacking from Oscar Wilson’s resume.

Motorcycle rider.

“Yeah, man, I waited until I got to 60-years-old to try and ride a motorcycle and I dumped it twice. It was crazy and I ended up with a broken bone … my wife is pretty hot about it … yeah, she’s real warm,” he recently said. “The bone that leads down the foot cracked. The doctors said it will heal up … but I’m done with that, man. That bucket list thing is over.”

Cracked bones from two-wheeled steel demons aside, things have been running pretty smoothly for Wilson and The Cash Box Kings during the first half of 2015.

The group’s latest album – the marvelous Holding Court (Blind Pig Records) – has struck a favorable chord with the blues-loving public, overseas and closer to home, as well.

“We just came back from Europe and we sold a bucket full of them (Holding Court) over there and people have been real receptive to it, pretty much everywhere,” he said. “And finally, it’s (the new CD) actually something that my family kind of likes. It’s something that they admit to liking, anyway.”

With his family firmly on board, there’s no holding Wilson and The Cash Box Kings back. Holding Court is nominated for Best Traditional Blues Album, while the group itself is up for Best Blues Band at this year’s Blues Blast Music Awards. Those looking for a refreshing mix of Chicago-styled blues from the ’40s and ’50s, but liberally dosed with 21st century themes and sounds, should at this point in time be well aware of just what The Cash Box Kings bring to the party.

“I would describe it (the sound of The Cash Box Kings) as a throwback to the golden age of blues, with some kickin’ fresh young blood, but yet not goin’ overboard. You can tell what it is without there being a bunch of notes in there sayin’ nothin’,” Wilson said. “You got a lot of people out there claiming they play the blues – and I’m not sayin’ it’s not the blues for them – but we try to stay with the traditional sounds, although our musicians are a little fresher. But our music is all about the feeling it gives you.”

Blues with a feeling is something that Wilson has known about from an up-close-and-personal perspective ever since he was a young child growing up on the south side of Chicago on 43rd Street in a six-room apartment split by two families. Back there, more than just idle noise in the background, music was almost like a weather forecast for young Oscar Wilson and his siblings.

“I was the youngest of nine children and I learned that the same song that made someone laugh could also make them cry. You understand? They (the adults in his house) would play this record by Junior Wells – “Come on in this House” – and a song by Little Milton – “Feel so Bad.” As children, we knew when those records came on that either something very good or something very bad was going to happen,” he said. “We would cry, ‘Please don’t put those records on,’ because we knew that something was going to go terribly well or terribly bad. A lot of things I truly didn’t understand back then, but that I remember.”

Wilson knew the words to a lot of songs – even back then – and could recite them at will, even if he didn’t know for sure just what those words that he was singing meant. However, he did know that the playing of certain records at certain times of the day meant good times for the family, while that same record spun at a different time could indicate things were not going to be so smooth.

“When my step-father and them would come home late and put on “Come on in this House,” that was a bad sign. But if they came home at the right time – the time they were supposed to – and that record went on, that was a good sign. A sign that we’d get some goodies and things,” he said. “That usually happened on Friday, when the eagle was flying, you know? But that’s how I learned that the same song that will make me laugh will also make me cry like a baby, because it’s attached to something.”

Unlike the lion’s share of bluesmen who went on to make a name for themselves in Chicago, Wilson was born-and-raised in the Windy City, as opposed to being born in the south and then working his way up north as so many before him did. Still, just as was the case with his southern brethren, the real-deal blues were not foreign to Wilson and his family in the big city.

“When I was real young, all the older guys would ask me, ‘How can you remember all the words to those songs?’ I knew them because I had heard them and they like went into my soul. I mean, we had a hard time growing up. We lived, ate and slept the blues,” he said. “That’s how it was with us. We had plenty of hard times. A lot of times we didn’t even have food. I had the blues and that’s how I was feeling.”

‘Feeling’ also sums up the way that Wilson approaches a song up on the bandstand. If it ever was in his plan of attack to separate the song from the way that it makes him feel, that plan would be doomed from the start.

“I do sing about how I feel. I can’t sing it (the song) verbatim, like I see most people do, because I may feel differently every time I sing a certain song. This day I may not feel the same way as the day I recorded it, so I can’t sing it exactly the same way, you see?” asked Wilson. “It’s really hard to explain, but that’s how it is. I sing like I feel.”

Called ‘the human jukebox’ by Billy Flynn, one thing that is constantly in the front of Wilson’s mind when it comes to working at his craft is to be himself and not fall into the convenient trap of trying to sound like someone else.

“I would love to sound like someone else, but I’ve had to make myself not emulate other singers. A lot of people say, ‘Hey, Oscar, you sound just like Jimmy Rogers.’ Well, before I started with The Cash Box Kings, I didn’t even know who Jimmy Rogers was. So I sound like me, and that may just happen to sound a little like Jimmy Rogers,” he said. “But I didn’t know who he was, even though I did hear his music. The mainstream was Muddy Waters, John Lee Hooker, Lightnin’ Hopkins, Jimmy Reed, Howlin’ Wolf and that’s who I knew. I didn’t know all the guys that were backing them up. I didn’t know about Jimmy Rogers and Eddie Taylor and all those guys back then. I mean, I didn’t know it was Eddie Taylor that made Jimmy Reed’s music sound so good, or how Jimmy Rogers made Muddy sound so good.”

Even though Wilson has played with Kenny ‘Beady Eyes’ Smith plenty of times over the past several years – in the studio and on the concert stage – there was a time he didn’t know he was playing with the son of Willie ‘Big Eyes’ Smith.

“No, I didn’t know who his daddy was at first, you know? Most of the white artists do all that research and they would tell me about all those guys, but I sure didn’t know all of that back then,” he said.

The same thing could also be said of Wilson’s knowledge of musical theory. Even though he’s self taught on the guitar, piano, drums and the harp, don’t expect him to deliver a seminar on what song is in what particular key.

“I didn’t know nothin’ about what keys songs were in. I’d just say, ‘Play it like the record and I’ll sing it.’ They’d start playin’ it and if I could sing it, I’d let ’em know,” he said. “But now I’ve learned what my strong keys are – like E, F, G. I can do some A’s and B’s, but those are my strong keys. And I have learned good players can play in any key. I used to be intimidated by that, but not anymore.”

It’s hard to think about The Cash Box Kings without the dynamic Wilson front-and-center these days, but at one time, the two were completely separate entities until a fateful meeting in Wisconsin.

“I had just moved to Janesville, Wisconsin in 2007 and was bored and went up to the corner VFW, where the paper said they were having a blues jam. I was just sitting there and this guy came up and introduced himself as Travis Koopman of The Cash Box Kings. He was the guitar player before Joel (Paterson). I told him I played a little harmonica and sang the blues, so he asked me to come up and jam,” said Wilson. “When I got up there, we just brought the house down. So he asked me what I was going to do and I said, ‘Man, I don’t know.’ I’d always had to take care of my kids and work and stuff, but I thought about it and told him I’d always wanted to play at Buddy Guy’s. He said, ‘Give me two weeks and I’ll be back.’ Well, two weeks later, I was playing at Buddy Guy’s.”

His talent was undeniable from the get-go, as Wilson was virtually born to play and sing the blues. But that didn’t mean that he was necessarily welcomed with open arms right of the bat by the rest of The Cash Box Kings.

“No, I wasn’t really well-received, because they were set in their ways. The leader of the band – Joe (Nosek) – was splitting vocals with Travis … and then here I came in. So it was a little rocky there,” Wilson said. “But now Joe is my best friend in the music world. But back then, the transition was not really easy. But we were made for each other and we quickly realized that. I mean, they had a great sound, but when they opened their mouths, it was the traditional white sound. I brought the flavor to it, you see? It was a marriage made in Heaven for both of us.”

While it may seem -at least from the outside looking in – that the members of The Cash Box Kings are all cut from the same cloth, Wilson says that couldn’t be further from the truth.

“The personalities of this group are so different. It’s like Joel Paterson is a freak of nature. When I first got to the group, Joel was stiffer (on stage) than he is now, but I make him go. I say, ‘Come on man, get up here!’ But he’s a genius. The music part of it, he puts together,” Wilson said. “When me him and Joe are on stage – which we’re primarily the ones that are there all the time – we have built a bond to where we know what the other will do before we even do it. Joe knows what I’m going to do before I do it … they feel me, you know?”

Chances are very good that no one who has ever caught the group doing their thing live has ever fallen asleep, or probably even batted an eyelash, when The Cash Box Kings are engaged on the bandstand. A lot of that is due to Wilson, who admits that he’s really a natural-born entertainer.

“Yeah, I am. That’s just the way I am. That’s just me and I’ve been that way since I was a child. My father, who passed away two months before I was born, was a bluesman. My mother and them knew a lot of bluesmen like Junior Wells and Big Smokey Smothers and Elmore James … Little Mack Simmons, Honeyboy Edwards,” he said. “They all used to come by my house and would sit there and play. As a little boy, I was always more interested in what they were doing than anything else. I never developed ball skills and all that, because I’ve always been involved in the music in some kind of way. That’s how I got started and I’ve always been willing to perform ever since then.”

Despite the fact that Wilson has been performing in front of crowds of all sizes and shapes since he was three years old, one thing has never changed over the course of all those years.

“Every time I perform, I’ll be so nervous that sometimes I have to throw up. To this day I have those feelings … it’s hard to explain. We just did the Chicago Blues Festival and finally some of my people came to see me (perform) and I’ve got a big family,” he said. “And it was like I had a panic attack or something. There were just some many people out there and even though I’ve played in front of many more people than that before, for some reason, I just couldn’t catch my breath. I wanted to do good so bad, I guess. Then my mouth got watery. I was telling myself to calm down. But Edward (Chmelewski) and Jerry (Del Giudice) said we put on one Hell of a show. I usually have that (nervous feeling) until I get that first note out of my mouth, but it was just super-bad that day.”

The Cash Box Kings are not the least bit hesitant to tackle issues that they see going on right outside their foot door, as evidenced by a pair of original tunes off Holding Court that Wilson and Nosek authored – “Download Blues” and “Gotta Move Out to the Suburbs.” The latter tune even has a cool video to go along with it that more than tells the story of the song (https://www.youtube.com/watch?v=lRioASJo5K4).

“I’m not the visionary writer of it – Joe thinks of these things – and I pump it up with my life. It’s (“Suburbs”) about me and about where I came from, 43rd Street,” Wilson said. “It’s (the song) like a changing of the guard … they tore down the projects and now have high-end houses and got stuff like Starbucks. When we were there, there was nothin.’ It’s changed so much, so Joe had the idea and I just dropped the facts in. We went around and I showed him the neighborhood and the places we used to be and we just shot the video on it. When we were shooting it, some of the people that I grew up with just happened to be around and it all just fell right into place. It was just like it was supposed to be.”

The title track of 2013’s Black Toppin’ sprang to life from a statement that Wilson made, a statement that he soon found himself having to tear down, piece-by-piece, in an attempt to explain its meaning.

“Were playing at a blues dance in Lafayette, Indiana and there were just so many pretty girls there and it reminded me of back when my mother and them used to be dancin.’ They would dress up and wear fine clothes and everything,” he said. “I said, ‘All these pretty women here, I’m gonna’ go black toppin.’ And he (Joe) was like, ‘What are you talking about?’ He didn’t get it. So I went home and wrote that song by myself. He just never got it. But now, we make a funny skit out of it on stage. I always say, ‘I’m from the public school, so I had to learn things fast.’”

As a youngster, one of Wilson’s close neighbors was none other than Robert Johnson’s one-time running partner – the late, great Honeyboy Edwards. Although Wilson says he went by another name back in the old neighborhood.

“Well, they call him Honeyboy, but my mother and them always called him Honeyman. If you said Honeyboy back in the neighborhood, they wouldn’t know who you were talkin’ about, cause he was Honeyman,” Wilson said. “He was always around and I was about 10 or 11 and we had walked up to the store and Honeyman was playing a house party. The other kids kept going, but I heard the music and stopped and stood in the doorway. Honeyman said, ‘Hey, little boy. You wanna’ come in and sing the blues?’ And I said, ‘Yeah, I do.’ He said, ‘What you wanna’ sing?’ I said, ‘”Two Trains Runnin’” And he fired it up and I went to singing it. Me and Honeyman’s daughter went to school together, too. And Big Smokey Smothers is my nephew’s father and he would come by the house; we’d call him the ice cream man because he rode a bicycle with an ice-cream thing (cooler) on the front of it. He always came by and brought us ice cream.”

The immediate area around Wilson’s house was stuffed to the gills with juke joints of all kinds, but his age kept him from entering many of them, although he still managed to hear a bit of the festivities that were going inside their four walls.

“Even though I couldn’t go inside, I’d go and listen. That’s when they had plenty of taverns in the neighborhood. There was always somebody playing,” he said. “I’ve always just loved the music that I heard coming out of those joints and I’ve tried to recreate some of that. Like “Hobo Blues.” I remember my mother working around the house and playing that, but I never really thought I could sing that. But Joel kept trying to get me to sing it and I said, ‘Man, I can’t sing no (John Lee) Hooker. But Joel kept on, so I finally sang it and we did it in one take (the tune can be heard on Holding Court).”

The way that Wilson sees it, there’s a huge difference between just singing the blues and SINGING the blues.

“Anybody can sing it, but can you SANG it, you know? You get all these hot-shots out there these days and they’ll finish playing and you’ll go, ‘OK, now where are you going?’ And then you’ll have some old dude come up that plays two strings and will knock you straight to the floor and you go, ‘Oh, my God.’ To me, that’s when I know I’ve felt the blues,” Wilson said. “If the song finishes and it make me want to have a drink or to cry or makes me feel nostalgic about something, then I know I’ve heard the good blues.”

There’s no doubt that just a few notes from Wilson and The Cash Box Kings can evoke all those emotions, plus a whole lot more. That’s a powerful thing and despite holding that power in the palm of his hand, Wilson is surprisingly not very enamored at his own abilities.

“I don’t like my own songs, I must tell you that. I’m not a fan of myself. I never listen to me. Once I do it, I don’t listen to it again. I don’t know why it (the finished product) doesn’t sound right to me, but it doesn’t,” he said. “I just try to stay in key the best that I can.”

Had Wilson never crossed paths with Koopman and The Cash Box Kings back at that open-mic blues jam in Wisconsin, there’s still a better-than-average chance that music would be an integral part of his daily existence in 2015.

“I would still be in music in some way. I was an All-City concert baritonist and All-City jazz trombonist (in high school). And I would have been a teacher; that’s what I wanted to be. I had scholarships to go to Jackson State, Grambling, Florida State and Knoxville College, but my mother didn’t understand the concept of a scholarship,” he said. “So I came home one day and was going to Devry to be a TV repairman and that was the end of it. There was no more conversation. Then I started having kids and stuff and got away from music, pretty-much all together. I’d stop by the joints every once in awhile and sing; I used to sing with Johnny B. Moore, who was Koko Taylor’s guitar player at one time. I also played with Melvin Taylor, too. When I first started singing with him, we’d do “Cadillac Assembly Line” and bring the house down. We would just kill it.”

It was during one of the times that Wilson was on stage with the immensely-talented Melvin Taylor where he witnessed something that had he not seen it with his own eyes, he might be hard-pressed to believe it really happened.

“We were playing at a little tavern on 44th and Whitworth in Chicago and he broke a string. Well, I’ve never seen a man’s hands move that fast. I’m not saying nobody’s done it – maybe Hendrix could be that fast – but I’m serious about what I’m about to say,” Wilson said. “He broke the string and never stopped playing. Every time I’d look around, he’d be reaching in this box. He never missed a beat and reached in that box, got an E string and put it on without ever stopping playing. I’d never seen anything like that in my life … I’m telling you, that was something else, man!”

Photos by Bob Kieser © 2015 Blues Blast Magazine