Time Traveling to Mid-1960s Chicago via AudioQuest's DragonFly Black and Red DACs

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Category: Art+Tech Art+Tech

August 2021

In 1940, Chicago was home to 278,000 black residents. Twenty years later, that number had climbed to 813,000—the result of a massive northward migration of African Americans, largely from rural parts of Mississippi, Louisiana, Alabama, Georgia, and Tennessee. The institutionalized racism in the South was at the root of much of this migration, but intertwined economic factors also shaped the movement.

During World War II, factories beckoned black southerners to industrial centers in the North, like Detroit and Milwaukee, but in the post-war years, as the factory jobs dried up, a secondary wave of migration began. Many black individuals and families completed their northward journey by moving on to Chicago.

For black musicians, the exemplar of what this looked like was McKinley Morganfield, who likely never used that name again once he hit Chicago in 1943. From the time he stepped off the train at Union Station, he was Muddy Waters to one and all.

Chicago/The Blues/Today!

Born between 1913 and 1915 (accounts, including his own, differ) in rural Mississippi, he sang in church, and bought his first mail-order guitar at 17. While he had performed part-time throughout the 1930s, his primary livelihood was driving a tractor on the 4000-acre Stovall Plantation, 60 miles south of Memphis, Tennessee. It wasn’t until 1941—after musicologist Alan Lomax had recorded Waters at Stovall—that the young man imagined that he might be able to have a career in music if he could get out of Mississippi. After arriving in Chicago and opening some shows for Big Bill Broonzy in the city’s black taverns, Waters set his sights on two things: quitting his job as a delivery-truck driver, and buying an electric guitar and amplifier so he could make himself heard above the noise in those rough-and-tumble clubs. In 1948, he recorded “I Can’t Be Satisfied,” a song with deep roots in Mississippi culture, and shortly found his music on every jukebox in Chicago’s black neighborhoods on the city’s south and west sides.

While many black musicians had made Chicago their home before Waters, his charisma and ability to surround himself with highly individualistic sidemen like pianist Otis Spann, guitarist Jimmy Rogers, and harp players “Little Walter” Jacobs, Junior Wells, and James Cotton placed him at the top of those struggling to make a living from music in the big city.

More than 15 years after Waters’s first hit record, he was still the highest-profile Chicago blues musician. The Rolling Stones had named themselves after one of his songs, he had toured England several times, and he had been featured at the prestigious Newport Jazz Festival. While he could still occasionally be found performing in Chicago’s working-class bars, more frequently he was on the road, playing racially mixed venues or on college campuses.

In the early 1960s, Waters’s growing reputation around the world—along with a sudden rise in popularity of older blues musicians like Skip James, Bukka White, Son House, and Mississippi Fred McDowell; artists who had never left the South and continued to play acoustic music—served to obscure the fact that Chicago was home to dozens of performers who regularly appeared in the black clubs.

While lesser known than Lomax, Pittsburgh-born musicologist Samuel Charters (1929–2015) was largely responsible for the rise to fame of many of those older blues singers who had remained in the South. Throughout the 1950s, he worked on what would become The Country Blues, a seminal 1959 book that opened the ears of a generation of listeners to previously obscure artists like White, Robert Johnson, Charlie Patton, Blind Willie McTell, Blind Lemon Jefferson, and others.

With that work behind him, in the mid-1960s Charters turned his attention to contemporary Chicago. Working with Vanguard Records, in 1965 he invited nine of Chicago’s headlining blues performers—“Homesick James” Williamson, Johnny “Man” Young, Johnny Shines, Otis Spann, J.B. Hutto, Otis Rush, Junior Wells, “Big Walter” Horton, and James Cotton—to record some samples of their repertoires, to be released on a three-volume series of LPs, each titled Chicago/The Blues/Today!

Chicago/The Blues/Today!

While marketed to reflect the contemporary sound of Chicago’s blues scene, the LPs actually featured artists that covered a broad swath of the city’s musical heritage. Williamson, who was 55 when he recorded for Charters, had moved north in 1932. Young and Shines had predated the arrival of Waters in Chicago by a couple of years. Among the headliners, only Cotton was a relative newcomer, having landed in Chicago in 1955, after establishing himself in Memphis.

Beyond the headline names, though, these recordings also captured the coming generation of players: guitarists Buddy Guy, James “Pee Wee” Madison, and Luther Tucker, harpist Charlie Musselwhite, and bassist Jack Myers, none of whom were over 30 in 1965.

Together, the 25 bluesmen who recorded for the three volumes exemplified what we’ve come to associate with the sound of Chicago blues: amplified guitars and harps, in-the-pocket rhythms, and a mixture of traditional themes and contemporary, urban issues. For a young black man in 1965, it couldn’t get more “today” than Wells’s song, “Vietcong Blues.”

I’ve cherished my original Vanguard LPs since I purchased them in the early 1970s, and was pleased to see Charters’s project get some appreciation as a Record Store Day (RSD) 2021 limited-edition release. Mastered from the original analog tapes by Kevin Gray, Chicago/The Blues/Today!, Vols 1, 2 & 3 (Craft Recordings CR00351) was pressed on 180g vinyl and limited to 3000 copies. Included in the package are Charters’s original liner notes, additional notes he wrote for a 1999 CD reissue, and an essay by the late blues historian Ed Ward.

Along with that limited-edition RSD release, Chicago/The Blues/Today! also finds new life as a 24-bit/192kHz digital download by Craft Recordings, which set me off on a journey to discover if digital technology could improve on what Charters had captured in 1965.

With an eye on how to get the best out of the FLAC files that sat in the Vox Music Player on my 2019 MacBook Pro, I decided to start with this benchmark sound chain: Fluance RT83 turntable ($349.99, all prices in USD), NAD PP 2e phono preamplifier ($189), NAD D 3045 integrated amplifier ($699), and Sony MDR-7506 headphones ($89.99).

When I lowered the Fluance’s tonearm on the first of my 50-year-old LPs, I was greeted with a typically shallow mid-1960s soundstage: the principal instruments pushed up prominently in the mix, and the bass and drums somewhere in the background. This type of sonic presentation was fabulous for the blues singers, guitarists, and harp players of the time; it gave them an urgency and a gritty, in-your-face personality. While you had to pay close attention to grasp what the bassist or rhythm guitarist were doing, there was no missing the power of Wells or Hutto as lead instrumentalists. It was music you felt, rather than heard. The best singers of the bunch—the highly expressive Wells and, on volume two, the rangy Rush—could really take advantage of this raw intensity. Every nuance was right there to be heard.

The room sound on the LPs was almost impossible to sense. Any reverb seemed to be a product of the performers’ instrument amplifiers, or something that was added by the engineer. Even when a tune ended or there was a rare quiet passage, it was hard to tell if the musicians were in a large studio or a tiny space. On some tracks, like Williamson’s version of his better-known cousin Elmore James’s “Dust My Broom,” it seemed like his drummer, Franklin Kirkland, was pounding on damp cardboard rather than on a resonant drumhead.

Prompted by that highly unmusical sound, I decided to make “Dust My Broom” the test subject for the hi-rez challenge. Could a digital file deliver more than vinyl?

I began with a straight run from my laptop’s audio output. As you might recall from a previous “Art+Tech” column, the notoriously fussy Neil Young once likened the MacBook Pro’s built-in digital-to-analog converter (DAC) to Fisher-Price technology, a comparison that I think is (just a little) harsh.

Kirkland’s drums sounded only slightly more musical, but the sound problems with “Dust My Broom” were exacerbated by the dynamics of the mix. Getting Williamson’s slide guitar and the rest of the band to a decent level had meant pushing his voice—not a thing of beauty—up to a decibel level that actually made me wince at its intensity.

AudioQuest Black

Next, I jacked my headphones into an AudioQuest DragonFly Black USB DAC and headphone amplifier ($99.95), connected to my laptop’s USB-C port via AudioQuest’s DragonTail-C Extender ($29.95). The DragonFly Black reflects its name with a matte-black finish that’s silky to the touch. It’s built around an ESS ES9010 DAC chip and outputs up to 1.2V to a connected preamplifier or set of headphones. Its Texas Instruments TPA6130 headphone amplifier has a 64-step analog volume control.

Back to “Dust My Broom,” and while Williamson’s voice remained as harsh as ever, the sound of the instruments leveled out, and Kirkland’s drum kit gained a bit more depth. I still wouldn’t call it musical, but at least it sounded more like drums than cardboard boxes.

AudioQuest Black

I decided to step it up another notch, and swapped out the DragonFly Black for its pricier sibling, AudioQuest’s DragonFly Red ($199.95). The Red’s finish is a fiery, glossy metallic, and its compact casing holds an ES9016 DAC chip with a 64-step, bit-perfect, 64-bit digital volume control, and an ESS Sabre 9601 headphone amp. With a maximum output of 2.1V, the DragonFly Red is compatible with a wide range of headphones, including low-efficiency models that require more power.

Both DragonFly models support up to 24-bit/96kHz PCM, so I adjusted the Audio MIDI Setup in my Mac’s Utilities folder to properly downsample the 24/192 FLAC file to 24/96. AudioQuest notes that both DACs perform MQA rendering.

With the DragonFly Red in place, the soundstage gained some depth and breadth. The dynamic balance between Williamson’s guitar and voice was much improved, and there was now enough detail to differentiate Kirkland’s snare from the other drums in his kit. His cymbals also became clearer.

Having been convinced that these sound chain adjustments could indeed enhance my enjoyment of the music, I dove back into the rest of the hi-rez FLAC file.

AudioQuest Red

It’s hard to justify Williamson’s presence in this collection. He had never been a full-time musician, having kept his factory job while playing second guitar with his cousin Elmore on weekends. On “Dust My Broom,” paying tribute to his cousin, who had died from a congenital heart condition in 1963, Williamson sounded tentative and his backing band—Kirkland and the stalwart Chicago bassist, producer, songwriter, and general fixer Willie Dixon—seemed under-rehearsed.

But Williamson’s inclusion is interesting, and speaks to some common elements on the Chicago scene. Tribute-paying between musicians wasn’t unusual, nor was borrowing heavily from rural Southern tradition. Elmore James—who, although he died in Chicago, had remained in the South for much of his life—had based his highly amplified, slashing style of playing on older musicians like Robert Johnson, Kokomo Arnold, and Tampa Red. The dance music James played related directly to the juke-joint tradition of the rural South, and his signature songs like “Dust My Broom,” “The Sky Is Crying,” and “Shake Your Moneymaker” used a lot of the imagery typical of Southern blues.

Like Williamson, J.B. Hutto was an energetic slide guitarist who was heavily influenced by the iconic James. His five performances here are filled with trebly guitar, exclamatory vocals, and a loose spontaneity that reflects the way Hutto’s band, the Hawks, would approach a club gig. Their material was highly riff-based, and pointed the way to the rise of Hound Dog Taylor and the HouseRockers: another Chicago band, which Hutto would eventually take over from its leader.

One of the oldest musicians on the series of LPs, Johnny Young had dropped out of music in the 1950s, but had been lured back by the rise of interest in the blues among white audiences following the British Invasion. Originally known as a mandolinist, he had predated Waters in adopting amplification to cut through the din inside Chicago’s clubs. Despite having a lower profile than many of the other musicians Charters featured in this collection, Young recorded six tracks in total, and most can be traced back to their rural roots, especially “My Black Mare” and “Kid Man Blues.” Young was a strong singer with an engaging delivery, and his performances were greatly enhanced by the presence of Horton, the superb harmonica player who also performed one song of his own on the third LP of the set.

Shines, 50 when the recordings were made, was another artist who never really left the South behind, despite moving to Chicago. He frequently traded on his close relationship with the legendary Robert Johnson, but he, too, had been passed over by those who were more interested in electric urban blues. The Charters project was his entrée back into recording, although his versions of “Black Spider Blues” and “Mr. Boweevil” betray his enduring relationship with rural music.

By contrast, musicians like Rush and Wells were clearly a generation apart.

Thirty-one years old when he recorded for Charters, Rush had established himself with a sound closer to jazz-influenced guitarists like B.B. King and T-Bone Walker, and his performances carried a more emotional punch than some of the older Chicago blues musicians who relied on traditional material. His band also stood apart from those who followed the Waters model because it included a saxophonist, Robert Crowder, rather than a harp player.

Like King, Rush loved the call-and-response of vocals and guitar, and Crowder’s alto sax provided a consistent harmonic base. Rush’s band was also beefed up by the presence of rhythm guitarist Luther Tucker, who’d go on to become a mainstay of bands led by Waters, Cotton, and John Lee Hooker.

Wells, who was 30 in 1965, stood apart because of his urban roots. Born in West Memphis, Arkansas, across the Mississippi River from Memphis, Tennessee, he had come to Chicago as a child, and presented himself as a streetwise showman throughout his career. Prior to joining Waters in 1952, he’d supported himself by playing on the streets. On the Chicago/The Blues/Today! recording, Wells was backed by his frequent foil, the estimable guitarist Buddy Guy, bassist Jack Myers, and veteran drummer Fred Below, and sounded fully ready for his star turn.

James Hale

In fact, Wells had recently recorded an LP, Hoodoo Man Blues, that would signal the rise of the new generation he and Guy represented. His exuberant, throaty voice and verbal asides gave him an air of confidence, and his outstanding harp work in combination with Guy’s sophisticated playing make his contributions by far the most exciting music in the collection. The emotion is palpable on “Vietcong Blues,” both in the vocal and Guy’s twisted guitar solo. It’s little wonder Guy was such an important influence on Jimi Hendrix, who was still developing his own style when Chicago’s fledgling Delmark Records released Hoodoo Man Blues in 1965.

Although they were also part of the younger cadre of blues artists who would go on to greater fame, Spann and Cotton had close ties to Waters. They often appeared as sidemen in his band, and Spann was also a relative by marriage. Both men were gifted musicians with distinctive styles, and Cotton became a highly effective bandleader who reached a wide audience through associations with the Rolling Stones and guitarist Johnny Winter. Unfortunately, Spann didn’t reach the same heights; he succumbed to liver cancer in 1970, just as he was gaining recognition beyond Waters’s immediate circle.

While it’s easy—from a distance of more than 55 years—to question the lineup Charters chose to feature on Chicago/The Blues/Today!, there’s no doubt that these records are an effective snapshot of one segment of the city’s musical landscape in 1965. Although thousands of African Americans left the South for what they hoped would be a better, less segregated life, they didn’t deny their roots. Even as they forged new lives in a burgeoning industrial city, the hamlets and country towns of the South remained in their blood. Charters’s great accomplishment was in assembling a rich cross section of the black musicians who undertook this journey—one that stretched from the Mississippi Delta to the shores of Lake Michigan.

. . . James Hale
jamesh@soundstagenetwork.com