It’s a reasonably safe bet that if you live anywhere in the Chicagoland area—the Loop, outlying neighborhoods, far-flung suburbs, any side of town—the Smiley Tillmon Band will find its way to your neck of the woods for a gig before too many weeks pass. They’re that busy.

“A couple of weeks ago, I did five in a row, but I can’t do that,” says Tillmon. “At my age, I can’t hack it because it takes too long to recuperate. But we do very well. We do about two or three nights a week. It’s good.”

There’s an obvious reason why the guitarist’s booking schedule is so jam-packed. As his nickname indicates, Smiley knows how to have a good time and makes sure his audience does too. After 55 years of playing the local blues scene, he remains happy to serve up the blues and soul standards that people never seem to stop craving. Tillmon does them his way, and his band—guitarist Kate Moss, bassist Tom Rezetko, and drummer George Baumann—provides just the right grooves to make Smiley smile.

Rezetko has been with Tillmon for a decade, serving in a variety of essential roles. “He’s my buddy and my manager,” says Smiley. “It’s like a chemistry. He seemed to understand where I was coming from, and I could understand where he was coming from.”

“It’s went really, really fast,” says Rezetko of their time together. “It’s been great. He’s just such a good friend.”

The two joined forces in 2007. “I met him through a guy named Marco. He’s a drummer. And he was working at Guitar Center out in Country Club Hills in the suburbs. I was strumming on a guitar, and he noticed when I was strumming. He said, ‘Hey, man, I like what you’re doing!’ So he invited me to a place in Blue Island called the Hideaway,” says Tillmon. “So I went by there. They had a jam session there. And Tom was playing there with a guy named Ronnie Prince and a guy named Kevin.

“I came up and started playing with Tom and Kevin and Ronnie. So me and Tom liked the way we sounded together. We did a few gigs with this guy named Marco, and after a while it looked like me and Tom had a little more in common than me and Marco did,” says Smiley. The deal was cemented when Tillmon and Rezetko dropped by another local jam. “We looked at each other and said, ‘Hey, man, let’s see if we can take this thing to another level!’”

Guitarist Kate Moss has been with Smiley’s combo for nearly five years, her slashing Freddie King/Magic Sam-influenced leads contrasting strikingly with Smiley’s fluid fretwork. “She just put another level on it. She took us places that I can’t give enough gratitude to Kate,” says Tillmon. “We like to complement each other, because she has a certain style of playing, and I have a certain style of playing. And it wouldn’t be a benefit if we all played the same thing. You need an off-and-on and a wet-and-dry, that kind of thing. I think the contrast makes it pretty good. She’s such a great player.

“Kate and Tom gave me the exposure so I could be where I needed to be.”

Tillmon was inducted into the Chicago Blues Hall of Fame on October 15. “You never expect this. You just try to do the best you can,” he says. “Thinking that I was deserving enough to be a part of it, now that really caught me by surprise. But you appreciate things like that, because you work hard and try to do good. So if somebody recognizes you trying to do good, that makes it all worthwhile.”

Smiley’s path to that honor has been singular. He was born Moses Tillmon in rural Jefferson County, Georgia. “In the cotton fields, because I wasn’t born in the city,” he says. “When you’re born in the woods like that, they just name the county because there wasn’t no town. And there’s no hospital, so you’re born in the house, the midwife, that kind of thing. But I survived.

“I stayed there in Georgia ‘til I was about ten years old, picking cotton and stuff in the meantime. Then my mom moved to Florida, Fort Lauderdale. So when I got to Fort Lauderdale, I went to school there and started picking beans down there in the beanfields. So one field to the other field,” he says. “I loved to sing. My mom was a pretty good piano player. I always wanted to play. So I finally went to the pawn shop and bought a guitar for ten dollars and bought a little chord book to try to figure out what to do. Eventually things started to happen for me. So I just kept working at it.”

There wasn’t much blues in the air where Tillmon was growing up, but he dug other genres. “I heard a lot of church music,” says Smiley. “I used to listen to country music, really. There was a lot of country music—the Grand Ole Opry, stuff like that. Because there weren’t too many black stations down there, so you could hear country music and stuff like that. And every once in a while, you would hear stuff out of Gallatin, Tennessee. There was a station that played a lot of stuff.” Hoss Allen’s broadcasts over Nashville’s WLAC-AM were eagerly anticipated. “He would play stuff by Louis Jordan, the guys out of the ‘40s and ‘50s,” Smiley says. “Every once in a while, you would hear it. His theme song was ‘Swanee River Boogie.’ I never forgot that.”

When he was old enough to get into the local clubs, Tillmon watched some of the greatest R&B performers on the planet perform live. “There weren’t too many places a lot of black artists could go at the time. This was in the ‘50s,” he says. “But there was a place between Fort Lauderdale and Miami called the Palms of Hallandale. And every time a good artist had a hot record, you could be sure that’s where they were going to come, because that was one of the big spots. I saw guys like Hank Ballard and the Midnighters. I liked that group. The ‘5’ Royales, and Bobby ‘Blue’ Bland when he was a young guy. B.B. King. All the guys came there. Little Willie John.

“You were inspired by all these guys. The ladies liked them. They had a lot of pretty ladies, so I wanted to be a part of that too! So hey, man, it looked like a pretty good idea,” says Tillmon. “The Palms of Hallandale, that was a hotbed where I heard a lot of the great players play.” The “5” Royales’ amazing guitarist Lowman Pauling mesmerized young Tillmon. “Oh, man, that guy that had that guitar hanging down low. He could pick it, man,” Smiley says. “He had this thing where he played those hot licks on it called ‘Think.’ I thought that was so cool when he hit those hot licks. I was impressed by him, man. And that (guitarist) with the Midnighters, Cal Green. He could play too. So those were the ones that really inspired me.”

Then there was the flamboyant Eddie “Guitar Slim” Jones, who would dye his hair to match his brightly colored suits and shoes and stroll through the audience thanks to a cord that was several hundred feet long. “I never met him, but I saw him. That’s when he had ‘The Things That I Used To Do.’ He could get it, man. He could really play,” says Tillmon. “He had that sound that nobody else had. It was sort of funky and jazzy, and he played real melodic, not just beatin’ on the guitar. He played lyrical kind of solos. That’s what I liked about him,” says Smiley. “He was saying something. He wasn’t just up there making noise. Guitar Slim was the man. He could get it. I was exposed to a lot of good people. I just sucked it all in, because I liked what they were doing.”

Pauling, Green, and Slim weren’t Tillmon’s only influences on guitar over the years. “I love B.B. I never like to copy his style, but I like the way he plays, and he was a good player,” he says. “I really love jazz too. I like George Benson. I like Wes Montgomery, but I actually like George better than Wes. And a guy named Grant Green. He’s a heck of a player. It’s like fixing a stew. You take something from everybody and put it in the pot and stir it up. So my pot is stirred up with some of everybody.”

Smiley’s first experience in a recording studio was with Miami singer Billy Miranda, possibly the session that produced Miranda’s explosive 1960 rocker “Run Rose” for Chicago’s Checker Records. “There used to be a club in Fort Lauderdale. It was a great club called the Downbeat,” he says. “I actually saw James Brown there, when he started out back in the ‘50s. Those guys used to come through there. I worked with Billy Miranda there, and then I worked with him in Miami at a place called the James Club.

“We did some stuff for a (producer) that lived in Miami Beach called Bobby Dukoff. It wasn’t my record. I was just on a session with this guy named Billy Miranda,” he continues. “You’re trying to get started, you don’t know what you’re doing. So you take it where you find it.”

Living in sunny Florida exposed Tillmon to an exotic musical strain. “When I went to school in Fort Lauderdale, a lot of kids’ parents were from Nassau. So there were a lot of Nassau kids around there, and they always liked to play calypso, do the limbo, and all that kind of thing,” he says. “At that time, Harry Belafonte was really popular, so everybody wanted to be like Harry Belafonte, that ‘Day-O’ kind of thing, and ‘Island In The Sun.’ So that’s what you could hear on the radio a lot. Naturally, you hear things on the radio you like, you try to do it.”

Tillmon left Miranda to join Sammy Ambrose & the Afro-Beats, who specialized in calypso. Ambrose was a Miami singer who doubled on drums; the rest of the Afro-Beats consisted of Charles Wright on the other guitar (not the fretsman who later fronted the Watts 103rd Street Rhythm Band), bassist Sammy Williams, and Joe Sanders on percussion.

“You know how you go to clubs and see people, and you talk and see what happens?” says Smiley. “I lived in a place called the Sir John Hotel. I moved to Miami after I graduated school in Fort Lauderdale. We just started playing, man. And I went to the see their show. They did the limbo and all the Caribbean stuff, and I liked that too. Because I’ve always liked everything. I don’t like to be labeled, because I love all kinds of music. You just sort of do good with what you do. But calypso was an amazing thing. I really enjoyed that.”

The Afro-Beats toured widely, venturing as far north as Montreal and Quebec City. They cut a 45 in New York that came out on the West Side label in the states and CMI north of the border. Coupling “Nitty Gritty” and “The Canadian Twist,” it was a lot more R&B than calypso. The band even had managers with an office in the Brill Building. “Our managers at the time set that up for us,” says Tillmon of the single. “We got some mileage out of it. We got some gigs out of it. I didn’t get no money, but we got some gigs!” When the Afro-Beats broke up in 1962, Ambrose stayed in New York (he would cut the original ‘64 version of “This Diamond Ring,” covered in pop chart-topping form by Gary Lewis and the Playboys). Smiley set his sights on a different metropolis.

“I didn’t want to go back to Miami, and I had met some people in Canada that knew people in Chicago. You know, you get off and you go to breakfast with different people, and you talk to people and ask them about whatever,” says Tillmon. “I knew one person in Chicago. I had got his number: Phil Upchurch. I met him when I was in Miami. I kept that number. He used to work with this guy called Dee Clark. You remember ‘Raindrops’? Before it came out, Phil gave me that record. (Phil) had one really big record called ‘You Can’t Sit Down.’

“When I left Canada, I had talked to a guy called Jump Jackson,” he says. “He was a drummer. He lived in Chicago. So when I decided to come to Chicago, I called those people to let them know I was in town. Jump Jackson hooked me up with this guy called Singing Sam.

“I went to this place called the Trocadero on the South Side of Chicago. It was about 47th and Indiana,” says Smiley. “Matt Murphy used to play with this band called Singing Sam & His Sparks. Singing Sam, I’ll tell you who his dad actually was, was Sam Chatmon. the guy (from the) the Mississippi Sheiks–‘Sitting On Top Of The World.’ That was his dad. I used to see him every summer. He used to come up here to Chicago.” That’s when Moses Tillmon received his lifelong nickname. “We were on the bandstand, and everybody used to call me Moses. And I like to have fun and laugh. (Singing Sam) said, ‘I ain’t gonna call you Moses. I’m gonna call you Smiley!’ That was in 1962. So I’ve been wearing it ever since.

“When I got to Chicago, everything was a lot of blues and a lot of soul music, that kind of thing. But blues was kickin’,” Tillmon says. “I ran into guys like Jimmy Johnson, Jody Williams, Lefty Dizz, Lonnie Brooks—he was Guitar Jr. then. So you know, I learned from those guys. They helped me out. A guy named Lacy Gibson. All these people, man. I’m in a debt of gratitude to all the people that helped me out.”

Tillmon worked during the mid-‘60s with keyboardist Billy “The Kid” Emerson, by then a South Side fixture but a Sun Records artist in Memphis a decade earlier with his Sam Phillips-produced classics “When It Rains It Pours” and “Red Hot.” “I worked some places with him. I worked some places in Waukegan, I can’t think of the name of ‘em, and some places in Chicago Heights. There used to be a hotel down there. And around the city,” says Smiley. “No big deal. Because he didn’t have no record then. He was just out there jobbing like everybody else. He had the name from ‘Red Hot.’ That’s where he had his little name from. We were all just out here, trying to make that little $15 a night. Lucky to get that!”

Smiley’s rhythm guitar was overdubbed onto “A Dancin’ Whippersnapper,” one of Emerson’s mid-‘60s singles on Billy’s own Tarpon label. “I wasn’t really that good a musician to be a session player, but he just liked what I was doing,” Tillmon claims. The song was penned by Emerson and newcomer Denise Craig, soon to find stardom as Denise LaSalle. “She used to work with Billy. She used to work with Singing Sam. She was always good, but she just needed a little tweaking up and a little nurturing. Billy really got her going,” says Smiley. “We started out with her in ‘64, ‘65, something like that.” The South Side was Tillmon’s primary stomping grounds. “I didn’t play the West Side a lot. I really liked to play the South Side,” he says. “But I used to work the West Side with Lee Shot Williams. I used to work over there with him a lot.”

Smiley’s first bout with full-time status as a musician ended in 1977. “My family came first,” he says. “I’m a family man. I had five kids, so I couldn’t be going nowhere.” So Tillmon found himself a day job. “I worked at a school district, maintenance and special ed, for 30 years to 2007, when I retired,” he says. “I took gigs, but that wasn’t my main thing at the time. I was working at the school. I was still playing though, when I had a chance to, when the job would allow me to.”

Sometimes that meant turning down very tempting offers. “Dick Shurman wanted me to play second guitar for Albert Collins. He brought me all the records and the albums that my buddies were on—Allen Batts was on there, and Johnny B. Gayden. I couldn’t do that because I was still home at the time. But Dick Shurman has always looked out for me,” says Smiley. “He helped me a lot. He always believed in me.”

Tillmon’s retirement from his day gig a decade ago resulted in a renewed commitment to playing his blues, this time as the leader of his own band. “I’m full speed ahead trying to play music now,” he says. “It was time to get back on the trail. Things have been going well since then, since I hooked up with Tom. He’s the best.”

Maybe that’s why Smiley is smiling more than ever these days. “That’s my whole attitude,” he says. “To play and have fun.” But those one-liners that he occasionally trots out to serve as between-songs patter? That’s another issue entirely.

“Sometimes the joke’s on me, because they’re sort of shaky,” he laughs. “I’m trying to get through the night. That’s all I’m trying to do. Man, I don’t know how good it is. But whatever helps me make it through the night, I’ll do it as long as it’s positive. I need a writer for some jokes. Do you know a good writer? I need it bad, man!”

Check out Smiley’s website at: http://smileytillmonband.com