Linsey Alexander started a second career in the blues at 58
After retiring from the police force, this larger-than-life guitarist and singer went from weekend warrior to international touring and recording artist.
by Steve KrakowFebruary 15, 2023
Since 2004 Plastic Crimewave (aka Steve Krakow) has used the Secret History of Chicago Music to shine a light on worthy artists with Chicago ties who’ve been forgotten, underrated, or never noticed in the first place.
It’s important to pay tribute to our living legends, and I like to think that the Secret History of Chicago Music does so at least as often as it honors the departed. Guitarist and singer Linsey Alexander has been laying down blistering electric blues in the Windy City for five decades, but he didn’t become a full-time musician and recording artist till after he retired from his job with the Chicago Police Department—and at that point he was nearly 60 years old.
Linsey Alexander, like many bluesmen before and since known as “the Hoochie Man,” was born July 23, 1942, in rural Holly Springs, Mississippi. His family worked as sharecroppers—an arrangement so exploitive it was a hair’s breadth from indentured servitude—but their fortunes changed for the better after his mother moved to Memphis to get a job. When Alexander was 12, she came back to take him and a sister to the city with her.
“When I got to Memphis, it was the first time I had ever seen a bus, or a street car. That was where I had my first hot dog. I didn’t know what it was!” Alexander told Blues Blast Magazine in 2020. “I used to go down on Beale Street to hear people playing music outside, but I wasn’t old enough to get in the clubs.”
After Alexander’s mother died in 1958, he stayed with an older brother. A friend of the family—Alexander knew him only as Otis—used to come by and play guitar. “I would listen to him. After some time, he started showing me some things,” Alexander said. “He would go off but leave the guitar. So I could practice what he had shown me until he got back.” Alexander started working to help support the family, taking jobs as a porter in a hotel laundry room and as a bicycle mechanic. But eventually Otis’s guitar fell into his hands for good. “One day he came out, played some guitar, and then said I’ll see you later. I haven’t seen that guy since then! Later on, I pawned that guitar to get the money for a bus ticket to Chicago.”
Alexander arrived in the Windy City in 1959, still a teenager and already a fan of blues, country, and the early rock ’n’ roll of Chuck Berry and Elvis (which wasn’t much different from rhythm and blues anyhow). He started hitting the south-side music scene, where he heard powerful soul singers such as McKinley Mitchell, Garland Green, and Bobby Day. “I saw Otis Clay, and on Wednesday nights I would go see Howlin’ Wolf,” he told Blues Blast. “On the weekend I would go hear Lefty Dizz and all of those guys. At the time, I was living on Ingleside on the South side.”
Alexander didn’t have a guitar of his own—Otis’s instrument remained in hock in Memphis—but after several years of soaking up music, he got the itch to start a band. “This one boy called himself a bass player. I knew I could play a little guitar. So he went and bought a bass guitar, then I bought myself another guitar,” Alexander told Blues Blast. “We found a guy to beat drums. Ended up calling ourselves the Hot Tomatoes!”
A club called the Place at 63rd and Champlain held a talent show every Sunday, and Alexander’s new band made a habit of playing a song at it each week. One of the numbers they had the most fun with was titled “Let It All Hang Out,” though unfortunately it wasn’t the 1967 garage-rock hit by the Hombres.
The Hot Tomatoes worked up a new tune every couple weeks, and Alexander soon started outpacing his sidemen. The band’s drummer was married with two kids, so Alexander replaced him with someone who could be more available. He also went through a few bass players, but soon he found the right one.
“In all of the years I have been playing, I have only had three bass players,” he said. “The third one, Ron Simmons, has been with me for over forty years. His brother, Walter ‘Simtec’ Simmons, had a hit record with his partner, Wylie Dixon called ‘Gotta Get Over the Hump’. That shit was hot, man!” (Secret History covered that band, Simtec & Wylie, more than a decade ago—and they were indeed hot shit.)
Alexander started to build a name for himself with his high-energy performances, bitingly distorted guitar tone, and deep, gravelly vocal style. He’s a big personality, with a lively sense of humor and an amiable, extroverted demeanor that makes him a natural at working the crowd.
At this point, though, Alexander’s music career had always been an evenings-and-weekends affair, squeezed in around the edges of his day jobs. In Chicago, he worked for a car dealer, at a gas station, and as a cook and busboy. In the early 80s he landed a position in the Chicago Police Department, which carried him through the rest of his workaday life. He retired from the force at 58, after he was wounded in the line of duty and decided he didn’t like the jobs that the department still had for him. Fortunately he started receiving his pension early, in 2000, and this ushered in a second act for Alexander as full-time bluesman.
Alexander had never had trouble landing regular gigs, but by the time he turned his full attention to music he’d spent around two decades slugging it out in south- and west-side nightclubs. In the late 90s, while he was playing at Red’s at 35th and Archer, an agent approached him with an offer of representation—and a promise of more money. At that point Alexander was averaging $150 per night, which didn’t go far toward paying a four-piece band.
The agent helped Alexander make connections on the north-side club circuit, and around the time of his formal retirement he cultivated regular gigs at B.L.U.E.S., Kingston Mines, and Blue Chicago. “I started working, and I ain’t never left the North side since then,” he told Blues Blast. “I’ve been playing there at Kingston Mines for about seventeen years now.”
In 1998, Alexander began selling his music on CD-Rs, circulating among the tables at the clubs he played and pitching patrons face-to-face. As of 2012, he claimed to have sold 8,000 copies of his first release, a four-song EP, at $10 apiece—and it’s just one of several he made over the course of more than a decade, including Someone’s Cookin’ in My Kitchen and My Days Are So Long. The CD-Rs may have been handmade, but the recordings were professional, usually cut in studios with full-fledged bands.
Alexander got his next break while sitting in with guitarist and CTA bus driver Toronzo Cannon at B.L.U.E.S. in 2012. Longtime Delmark Records recording engineer Steve Wagner was running a live broadcast from the club, and he was impressed enough with Alexander to recommend him to label owner Bob Koester. Delmark had been issuing blues LPs for more than 50 years at that point, and later in 2012 the venerable label released Alexander’s first properly distributed album, Been There Done That.
The LP shows off Alexander’s time-tested skill, fusing blues, funk, and soul with seemingly effortless improvisatory flair and a wizened, gritty sound. Alexander wrote or cowrote 11 of the album’s 12 tracks, and veteran harp player Billy Branch appears on three cuts.
Alexander continued to release music through Delmark, including the albums Come Back Baby (2014), Two Cats (2017), and Live at Rosa’s (2020). The live album, which is still his most recent release, came out after new Delmark owners Julia A. Miller and Elbio Barilari took over in 2018, and Alexander has good things to say about the change. “They seem to be doing more for the artists, like getting the artists out there with advertising. I look at social media almost every day, and I see myself out there,” he told Blues Blast. “They are a great bunch of people. They do what they say they are going to do.”
At 62, Alexander married for the first time, though he’d already had children in a previous relationship. His son Nick, who’s now 21, also plays blues guitar professionally. Alexander was inducted into the Chicago Blues Hall of Fame on June 8, 2014, having worked with a staggering list of legends—among them B.B. King, Bobby Rush, Buddy Guy, Artie “Blues Boy” White, Little Milton, Magic Slim, Johnnie Taylor, A.C. Reed, John Primer, Otis Clay, and Eddie Clearwater.
At 80 years old, Alexander isn’t as vigorous as he used to be, even though he doesn’t drink or smoke. But he continues to gig, sometimes sitting in with Nick’s band, and he appeared last Labor Day weekend at the Rockwell Street Stroll presented by Delmark and Earwig Records. If you’re wise, you won’t pass up your next chance to see him—I recommend you keep an eye out for a big gig in June.
“When you come to my show, you won’t have to worry about it being boring. I will always do my best to make you happy, keep you smiling, and get you excited,” Alexander told Blues Blast. “I play some real serious blues, too, the kind that make you want to drink your whiskey down. I am who I am. I’m not trying to be B.B. King, or Freddie either. I do the best of me of anybody in this world!”
The radio version of the Secret History of Chicago Music airs on Outside the Loop on WGN Radio 720 AM, Saturdays at 5 AM with host Mike Stephen. Past shows are archived here.