James ‘Tail Dragger’ Jones, one of Chicago’s last links to golden age of blues, dies at 82

By Chicago 8 Min Read

For decades, as if possessed by slow blues licks, Tail Dragger Jones crawled on all fours among the hightop tables of Chicago blues clubs, his cowboy hat and boots moving in time, belting his gravelly growl into a mic.

He’d stand and sidle through the crowd, smiling, leaning close and singing to women, often his classic “My Head Is Bald.”

“Women were hiding legs and pulling dresses down,” said Mary Lane, 87, a fellow Chicago blues singer. “I thought it was funny.”

He learned the stage antics from his hero and mentor, the legendary Chester “Howlin’ Wolf” Burnett, whose floor routine was all the more astonishing because he stood six-and-a-half feet tall. 

There were many Howlin’ Wolf imitators — known as wolf descendents — but Tail Dragger rose above and outlasted the pack.

He was practically anointed by Howlin’ Wolf, who he gigged with, and who assigned Mr. Jones his Tail Dragger nickname because he was always running late.

In recent years Mr. Jones represented one of the last links to a nearly vanished era.

“We’d often talk about how we were some of the only ones left who did the real old-school blues in Chicago,” said friend and fellow bluesman Willie Buck, who came to Chicago from Mississippi during the Great Migration that brought many blues legends North.

“These young guys now, they never picked no cotton, never pulled no corn, never drove no tractor, plowed with no mule.” 

Mr. Jones died Sept. 4 from natural causes. He was 82.

Chicago bluesman Billy Branch played “Amazing Grace” on harmonica at Mr. Jones’ funeral earlier this month.

“He was raw, gritty, 100 % in-your-face, unadulterated, pure West Side blues,” Branch said.

Mr. Jones was born Sept. 30, 1940, on a farm in Altheimer, Arkansas. His parents, Pearl Robinson and Haywood Jones Jr., separated when he was young and Mr. Jones was raised by his grandparents.

He served in the Army before moving to Chicago in the ’60s.

“He was singing blues when it was still the music of Black Chicago in clubs on the South and West Sides for Black audiences before it became a sort of touristy music and was mainly seen in clubs on the North Side,” said Dave Waldman, a former bandmate.

Waldman, a harmonica player, was a University of Chicago student when he first saw Mr. Jones play in the late ’70s and eventually got the chance to sit in — a tradition in blues that allows for other musicians in the room to get on stage and perform with the band for a song or two.

He eventually asked Waldman, who is white, to join his band and concocted a unique origin story.

“This here’s my son,” he’d tell audiences. “We came up here from the South and when they saw we were different colors, they were going to hang me and raise him, so I put him in a paper bag where he couldn’t be seen and kept moving North to Chicago, and when he’d start crying, I put a harp in his mouth and he’s been blowing ever since.”

Waldman introduced several classmates to Mr. Jones who also played with him. 

“It was a passport into a whole different, amazing world at these West and South Side clubs,” said Johnny “Rockin’ Johnny” Burgin, a classmate of Waldman’s.

One famous West Side venue was the Delta Fish Market, where you could buy live catfish out of a tank, and listen to blues on a plywood stage in the parking lot.

“It was free and open to the public and just had a city wildness to it. There could be Black motorcycle gangs and people there with their families. It was a street party,” said Bob Corritore, another bandmate.

It was also where another bluesman, Bennie “Boston Blackie” Houston, confronted Mr. Jones in the wee hours one summer night in 1993 and Mr. Jones fatally shot him in the left eye with a pistol.

Bad blood that partially stemmed from a financial dispute had lingered for weeks.

Houston had been looking for Mr. Jones, who feared a beating, said Martin Lang, another bandmate, who saw Houston earlier that night near the fish market “tapping a pipe into his hand on the sidewalk.”

After the shooting, Mr. Jones turned himself into police.

The father of Burgin’s University of Chicago roommate was prominent attorney Marshall Patner, who took on Mr. Jones’ case pro bono. Mr. Jones ended up serving 17 months of a four-year sentence in a minimum security prison downstate.

“He said it was like going to a rest home, and prison was easier than the Army,” Lang said.

After his release, Mr. Jones recorded several albums, signed with Delmark Records, and began playing gigs in Europe and South America, where he gained a following in countries including Brazil and the Netherlands. He also released a collaboration album with Corritore through the Delta Groove label.

About a decade ago, Mr. Jones was in Switzerland for the Lucerne Blues Festival and found himself performing in a trio for a group of city officials in the mayor’s office.

“Their culture is one of formality, and Tail Dragger was giving it his all but finding it hard to break through. And he always needs to get a bit back from his audience,” Corritore said. “So he got on his knees and crawled over to the city officials singing. The mayor was a bit squeamish but finally got over it and had to smile. Tail Dragger made everyone an accomplice in his show.”

In 1998, on the 25th anniversary of the day he went to prison, Mr. Jones played a show for a group of shackled inmates at the Cook County Jail.

He also performed annually at the block party in his North Austin neighborhood.

He was married six times and always had a few sources of income that ranged from fixing diesel engines to driving trucks and selling moonshine liquor he brought up from the South.

Mr. Jones was primarily a singer.

“He said he used to play the guitar before a transmission fell on his hand,” Lang said.

Mr. Jones is survived by his wife, Bertha, six children, two stepchildren, 25 grandchildren and many great grandchildren.

Services have been held.

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