A fixture on the Chicago blues scene since his teens, Billy Flynn is one of the most soft-spoken and understated guitarists in the Windy City. But despite his modesty, he’s unquestionably an international star of the brightest magnitude — the go-to guy for anyone wanting to round out an all-star band or add polish to a recording session.
He frequently pops up in various top-notch musical collectives. A former fixture in both The Legendary Blues Band and Chicago-based Mississippi Heat, he’s been touring most recently as a member of harmonica player Mark Hummel’s star-studded entourage of merrymakers as well as the revolving lineup of The Cash Box Kings. And his fret work has been a key part of seminal blues recordings for decades.
As a front man, Flynn works in several different band configurations across the Midwest, and appears regularly in Windy City for regular monthly gigs at Shaw’s Crab House on the near North Side and B.L.U.E.S. on Halsted and the Smoke Daddy barbeque franchises, too.
As a recording artist, his work graces dozens of CDs. His most recent solo disc – Lonesome Highway on Delmark – was a 2017 Blues Blast Music Awards nominee for traditional blues album of the year, and he’s released albums as a surf rocker and mandolin player, too.
Through it all, Billy remains true to the music and an independent contractor at heart, crisscrossing the planet and delivering some of the most stylish fret work imaginable no matter where he appears. This past summer alone, he made three separate forays across Canada, hopscotched across Europe and played at several major American festivals, too.
“I’m really not with anybody,” he insists. “I do freelance – and that’s definitely by choice. It’s something I’ve always done because it doesn’t limit me when it comes to making decisions that benefit me and the folks that I play with.
“And I love the concept of collectives and the nice shows they put together.”
A native of Green Bay, Wis., Flynn came into the world on Aug. 11, 1956, destined to play stringed instruments. As a toddler, he’d grab toy guitars off the shelves when his mother pushed him through stores in a stroller. He and his siblings played homemade instruments in the family’s garage, using barrels for drums – Billy’s first “instrument” – and makeshift guitars with rubber bands used for strings.
As a small child, he started out on ukulele because, he says, a guitar simply was too big for his small hands. But even then, he thought of himself as a guitar player. His passion for the blues came early through the seminal work of Elvis Presley in the ‘50s. The blue notes of such chart-toppers as “Jailhouse Rock” and “Kid Creole” struck Billy to the core and started him on a search for the font from which the sounds flowed and for the people who made it.
His love for surf came about after a family friend gave him a copy of The Ventures’ hit, “Walk Don’t Run,” featuring the six-string mastery of Nokie Edwards. “Everybody thought ‘Walk Don’t Run’ was easy to play until they really started to play it,” Flynn says today. “To know each and every corner of that song, you had to be a pretty good guitar player to play some of it.
“It took me a lo-o-ong time ‘cause I taught myself how to play guitar by trial and error.
“With that kind of music, I’d put it on tape and play it over and over until I could figure out what was goin’ on. With blues, I never had to do that. Blues and jazz were more improvisation. That (surf) was more something that you had to have together.”
He got his first real six-string at age 10 – a $10 acoustic that he purchased himself after putting down a $1 deposit.
“I think I already played guitar before I actually owned one,” he says, because I was visualizing it in my mind. I went home to my mom and told her: ‘I bought a guitar today.’ I put a dollar down on it.
“And I didn’t ask her. I just did it!”
Billy quickly learned his guitar ABCs – chording, strumming and picking – by ear, and he admits today that he’s never been skilled at reading music. His first venture as a musician came as a drummer in garage bands – beginning with The Blues Express at age 14.
“I kinda faked my way through that,” he admits. But there was no faking his love for the blues.
“It’s infectious,” he says. “When I heard it, I felt like movin’!”
And the blues attracted him in other ways, too.
He was fascinated by the lyrics contained in the 12- and eight-bar measures – so much so that he spent hours in the library in sixth and seventh grade poring over whatever blues books he could find in an effort to soak up the true meaning of the words that concealed carefully veiled messages – many of them too “adult” for tender ears — between the lines.
He purchased his first electric guitar – what he now realizes was a cheap Japanese knockoff — at age 13 from Green Bay’s Stiller Music, laying down a $10 deposit on the counter, after falling in love with its look as it rested in a display case. The first time he saw it, it listed for $300. By the time he bought it, the price had been slashed in half.
And once again, his mother found out after the fact.
Billy paid off both instruments with money earned from a paper route and by shoveling snow in the long Northern winter. Any free cash went toward purchasing albums by Chuck Berry, B.B. King, Fats Domino, Bo Diddley and Muddy Waters, which broadened his skills as he played along with the records.
Later on, he discovered first-generation acoustic blues on the radio, and he fell in love with the way Tampa Red, Lil’ Son Jackson, Big Bill Broonzy, Lightnin’ Hopkins, Lonnie Johnson and Robert Nighthawk made their instruments sing.
Billy loved the sounds of the Allman Brothers and other bands of that era, he says, but avoided their music. Even at that young age, he believed that his playing style, which was heavily influenced by ‘50s and ‘60s traditional blues, would somehow change by osmosis.
The blues truly came calling on Flynn within a year of him picking up the electric guitar for the first time.
The invasion began when Luther Allison played at a festival not far from Billy’s home.
A man who moved with his family from his native Arkansas to in the Windy City at age 14, Allison’s big break came when Freddie King invited him out of the audience to share the stage. His recording career began in the ‘60s and included stops at Delmark, Alligator, Motown’s Gordy imprint and a host of European labels, and he was the reigning male artist of the year in the blues world when he succumbed to lung cancer a few days before his 58th birthday in 1997.
Young Billy didn’t even know Allison’s name at the time. But he quickly understood what his elders already knew: that Luther was something special. To his ear, Luther was a cross between Buddy Guy and Magic Sam. Not only did he possess some of the best dynamics in the business, going from a whisper to a scream in a heartbeat, but even though he was very powerful, his play was also very clean.
Trading licks with the legend at Duck Duck Goose, a Green Bay institution that hosted many of the top blues acts of the era, later on in his youth remains one of Flynn’s favorite memories today.
Billy was still 14 or 15 himself when his dye as a bluesman was cast for good – thanks to a street-smart pool hustler named J.C. who looked older than his 18 years and booked the bands Flynn played in during high school.
J.C. insisted that Billy join him to hear Jimmy Dawkins, who was playing at Clark Kent’s Super Joynt, a comic-book themed blues club that had a brief run in Green Bay in the late ‘60s and early ‘70s. Designed by artists who went on to work on the Star Wars franchise, the stage resembled a cave with icy stalactites and stalagmites.
Revered by Eric Clapton, Guy and Stevie Ray Vaughan. Jimmy was at the height of his fame at the time after releasing his debut LP, Fast Fingers, two years before.
Billy brought his guitar along that night, and was sitting on the bar’s back steps with his guitar out of its case — too young to enter – when Dawkins and his band wailed away inside. When the band took a break, Jimmy’s drummer, Lester Dorsey, stepped out for a breath of fresh air.
“He was really helpful to me,” Flynn remembers, “’cause I was just sittin’ there with my guitar, and he asked me: ‘You gonna play?’
“I told him I couldn’t get in.”
That changed – and Flynn’s life did, too – when Dorsey ducked back inside.
Apparently Billy had made quite an impression because the drummer immediately reported his discovery to his boss. As Billy’s mentioned in previous interviews, Dawkins subsequently approached the club owner and sought permission to bring Flynn in to play on the next set. The proprietor agreed – providing the youngster promised not to drink.
Dawkins had a style all his own, Flynn remembers. People tabbed him with the nickname “Fast Fingers” – which he grew to hate over time – for a reason.
“With a guitar, you have a left hand and you have a right hand,” Billy notes today. “Some people are fast with one or the other. Jimmy was really fast with his right.
“If you listen carefully, you can hear the similarities between what Jimmy and (surf guitar giant) Dick Dale did. Jimmy called it ‘triple trebles’ – when he would slide up real high on the strings. But he also did it on the lower strings, which had a really cool sound.”
That night was the beginning of a beautiful relationship that endured for years.
Another began a week later, when Billy and J.C. returned to the club to catch John Littlejohn in action.
One of the best slide guitarists in blues history, Littlejohn migrated from Mississippi to New York and Gary, Ind., before settling in Chicago, where he was a force into the early ‘90s. Before a career with releases on Arhoolie, Chess, BluesWay and others, he reportedly served as an occasional rehearsal musician for the Jackson Five, a position acquired through his friendship with family patriarch Joe Jackson while he was living in Indiana.
Littlejohn’s version of the 1960 Brook Benton hit, “Kiddio,” quickly became a blues standard after Littlejohn reinterpreted it under the title “Kiddy-O” about a decade later.
His style immediately caught Billy’s attention.
“When I heard Johnny play slide, it was the sound that I really liked – real clear,” Flynn recalls. “The way it was executed, you knew he knew what he was doin’. It kinda reminded me of Hawaiian guitar because of the way he was playin’ it – slidin’ chords up from the bottom of the neck and things like that.
“He could really make that guitar talk. It was completely free of the rock sound you’d get from Eric Clapton and Duane Allman. It had a real Mississippi, country sound to it.”
“I miss the guy…I miss him!” he says, noting that he was just as powerful a picker as he was with the slide in his hand.
“I actually have a recording of him playin’ with Howlin’ Wolf,” he adds. “Johnny would have been a permanent member of his band if things had been different. But I think he wanted folks to know there was more to him than just that (slide).
“He talked about it in an interview on the Arhoolie website (https://arhoolie.org/john-littlejohn-interview/).
“If you listen to all his work, you can tell that he was really great at playin’ single-string leads like B.B. King. Plus, he did the Elmore James-type slide. When I started playin’ with him (later on in Chicago), I was thinkin’ there was gonna be a lot more slide goin’ on. But I think he wanted people to know that: ‘Hey, I’m not one-dimensional!’
“I loved the way he played both things.”
Another artist who gave Flynn encouragement during those early years was Mighty Joe Young, another giant who was always easily accessible.
Like the others, Mighty Joe had a distinctive guitar style that set him apart from the crowd. He grew up in Louisiana before migrating to Milwaukee and then Chicago, where he worked behind Otis Rush, Magic Sam, Jimmy Rogers and Tyrone Davis before setting off on his own. His first venture into a recording studio took place at Bobby Robinson’s legendary, Harlem-based Fire Records in the early ‘60s. The session took place at the suggestion of Elmore James, who was in the label’s stable.
Immensely popular in the ‘70s and ‘80s after releasing Blues with a Touch of Soul on Delmark about a decade later, he’s one of the most tragic figures in blues history. His career came to a halt experiencing complications that robbed him of feeling in his fingers after he underwent surgery to correct a pinched nerve in his neck.
“He was very friendly, and always invited me to sit in,” Billy recalls. “He was a great leader, and he excelled at second guitar. His playing, even in the beginning, was hot!
“The thing about Joe Young was that, the people who played with him, they were lifers. They stayed out with him for 10 years. I really enjoyed that band a lot.”
Three of those bandmates remain active today: bass player – and Freddie King’s brother — Benny Turner, drummer Willie “The Touch” Hayes and keyboard player Ken Saydak, a vital component of Rockwell Avenue Blues Band, the collaboration of four Windy City veterans who made waves last year with the CD Back to Chicago.
Flynn and Dawkins became fast friends, a relationship that grew stronger every time they met. Four years after their first encounter, Jimmy invited Billy to join his band. It was quite an honor when you consider that his second guitar chair had previously been filled by Jimmy Johnson, The Barroom Preacher, and Rich Kirch, who played alongside John Lee Hooker for the final 13 years of his life.
Still in his teens, Billy quickly found himself welcomed with open arms by many of the biggest names in the history of the music. Not only was he working with Dawkins and Littlejohn on occasion, but he was also rubbing elbows with Jimmy Rogers, Sunnyland Slim, B.B. King and a host of others on a regular business.
And all of them were mere mortals, not gods. It didn’t take long for Flynn to realize that, like him, they were all struggling to make a living, too.
Fortunately, however, through it all, Billy was never shy.
“When I see or hear something that I enjoy, I’ve always had no reservations about talking to somebody about what they do or how they do it, and it’s always worked out real well for me,” he insists.
“My biggest hero was B.B. And when I met him, he wasn’t such a well-known person. We talked a long, long time. He really enjoyed people and having conversations. And I got to run into Scotty Moore (of Elvis fame), James Burton, Franny Beecher of Bill Haley & His Comets and Al Casey (Duane Eddy), and I got to sit and talk to all of them.”
Although he never met Albert King face-to-face, he did see him frequently, and learned something about himself in the process.
“When Albert played left-handed, it made me realize that I’m slightly ambidextrous,” Billy says, “because I can flip the guitar over and play it left-handed, too. I have no problem in my brain flipping everything upside down — so I can understand what he and Otis Rush were doin’.”
Flynn quickly became a member of Dawkins’ family, staying in Jimmy’s home as he split his time between Wisconsin and Chicago. Their relationship that endured for almost 40 years until Jimmy’s death at age 76 in 2013. They were together on stage at Smoke Daddy in Jimmy’s final public appearance.
Despite making a name for himself in the Windy City, Green Bay remained Billy’s home. He and wife Mary hosted the popular Blues in the Park concert series for the better part of 30 years. A one-day event conducted every August, it drew top artists and throngs of blues lovers to Titletown, but came to an end when the Flynns relocated closer to Chicago in 2011.
Now in his early 60s, Billy’s still practicing the lessons elder bluesmen taught him in his youth. And those late-night studies in smoky bars have served him well. His career includes a handful of releases as a band leader and recordings with everyone from Bob Corritore, John Primer, Kim Wilson, Barrelhouse Chuck and Jimmy Burns to Lurrie Bell, Jody Williams, Billy Boy Arnold, Rockin’ Johnny Burgin, Pinetop Perkins, Willie “Big Eyes” Smith and many more.
If you’re a fan of the film Cadillac Records, that’s Billy playing the lead on the Etta James cuts as well as the Chuck Berry character’s version of “Surfin’ U.S.A.”
A modest, down-to-earth star in his own right, he’s a 2016 inductee in the Chicago Blues Hall of Fame. And he became a member of the Wisconsin Area Music Industry Hall of Fame in 2018 along with Bryan “The Braille Blues Daddy” Lee. A native of Two Rivers, Wis., Lee credits Flynn with instilling his love for the blues.
No matter where he is or what he’s doing, Flynn remains humble and supportive of fellow musicians in whatever way he can – always as a team player who never attempts to steal the spotlight for himself.
He does have a few regrets, however. Missing out on the chance to see Earl Hooker, Otis Spann and Magic Sam live — all of whom probably appeared at Clark Kent’s in his childhood – is one. Not getting to see Eddie Taylor Jr. — a close friend who passed earlier this year – assume his birthright as the future of the blues because of the health problems that plagued him most of his life is another.
And misses out on not having had the opportunity to play with two other artists who left us wa-a-ay too soon: Atlanta-based Sean Costello (the Blues Blast Music Award for rising star is named in his honor), who succumbed to an accidental overdose of prescription drugs at age 28, and Maine-born Nick Curran, who lost a valiant battle against oral cancer at age 35.
But blues remains in some great young hands, Flynn says. Among the artists he enjoys listening today are guitarists Toronzo Cannon, Marquise Knox and Christone “Kingfish” Ingram and Rei Lee Kanehira, known as “Miss Lee,” the Japanese-born lady who’s continuing the legacy of the late Barrelhouse Chuck and David Maxwell by breathing new life into the Chicago blues piano tradition.
If you have your sights on career in music, Billy has some simple advice. “Right now is a great time to be playin’ guitar,” he says, “because it’s easy to get a good one. Just keep playin’ it, listen to records and go to a lot of jams. Talk to musicians ‘cause most musicians will help you – like they did with me.
“If you’re truly determined to learn, don’t be afraid to approach anyone. Chances are pretty good that they’ll lend you a hand.”
And that includes Flynn himself.
“The name of the game is to keep busy, keep learning and keep trying to make people happy,” he says, noting that he intersperses his touring schedule with gigs with his own band, the lineup of which is flexible much like his big gigs with a regular, alternating cast of musicians.
“I try to learn somethin’ from everybody. And I’m always willin’ to work with new artists. I always try something new every day and different styles of playing guitar.”
Check out where Billy’s playing next as a band leader by visiting his website:
www.billyflynn.com. And be sure to check out the websites of the other bands mentioned here because it’s a good bet that he just might show up for their gigs, too!