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.

As much as people love the famous songs of so-called one-hit wonders, they don’t get much respect. Legit soul and R&B hits such as Jean Knight’s “Mr. Big Stuff” or the Capitols’ “Cool Jerk” often get lumped in with novelty numbers (Carl Douglas’s “Kung Fu Fighting,” Vicki Lawrence’s version of “The Night the Lights Went Out in Georgia”) on cheesy nostalgia-bait compilations. It’s especially sad when an artist tagged a “one-hit wonder” actually had a substantial career making quality music, with a long list of forgotten minor successes in addition to their immortal smash. Such is the case with singer Jackie Ross.

Jaculyn Bless Ross was born January 30, 1946, in Saint Louis, Missouri. Her mother and father were both preachers, so she started singing gospel at an early age—her first performance was on her parents’ radio show at age three. After Ross’s father died in 1954, her family moved to the Windy City, and when Ross was a teenager, she was recruited by Sam Cooke, a friend of her mother’s, to record for his SAR Records imprint.

Billed to Jacki Ross, the 1962 SAR single “Hold Me” b/w “Hard Times” could’ve been a chart-topper packing dance floors coast to coast—Cooke cowrote the A side, and Ross wrote the flip—but it didn’t end up selling well, possibly because Ross’s mother wouldn’t let her tour to promote it. Cooke would be dead within two years, but Ross’s career would get a bigger boost from another famous singer after she entered a talent contest at the Trianon Ballroom in Woodlawn.

Syl Johnson‘s band was playing there, and I won a singing contest,” Ross says in Robert Pruter’s 1991 book Chicago Soul. “The award was a weekend of singing and being paid. And that started me singing in Syl’s band. We worked a lot of places, and I was working with Syl Johnson when Bill Doc Lee discovered me.”

Bill Lee was a gospel DJ at WVON-AM radio, which was part owned by Leonard Chess. Lee took Ross to Chess Records, and in 1964 she signed to the legendary label. Ross’s first single for Chess, “Selfish One” b/w “Everything but Love,” became her big hit and her cross to bear, as she would never match its success.

“Selfish One” reached number 11 on the Billboard Hot 100, number four on the Cashbox R&B chart, and number five on the Canadian RPM chart, and it’s easy to hear why—the production is immaculate, and Ross’s elegant voice is beyond smooth but still elastic and emotive. Carl Smith, who would later cowrite “(Your Love Keeps Lifting Me) Higher and Higher” and “Rescue Me,” is one of the songsmiths credited on “Selfish One.” The tune has a similar feel to Mary Wells’s “My Guy,” and may have been an attempt to mimic its appeal, but in this author’s opinion Ross’s hit is infinitely superior.

Ross’s other 1964 singles didn’t do nearly as well, unfortunately. “I’ve Got the Skill” b/w “Change Your Ways” made it to number 89. The snappy “Jerk and Twine” b/w “New Lover” (the latter is a reworking of “Everything but Love” that references Chicago and the hit “Twine Time” by local hero Alvin Cash) stalled at number 85. “Haste Makes Waste” b/w “Wasting Time” only got to number 126.

The 1964 LP Full Bloom collected many of Ross’s singles for Chess alongside some newly released material (including a cover of Gershwin’s “Summertime”). The album has become a sought-after rarity, with original copies often fetching $200 or more. Ross also joined a Chess Records package tour that included Fontella Bass, Little Milton, and the Radiants. “We called ourselves the Chess family, ’cause at each theatre everybody would pitch in and make it very enjoyable,” she says in Pruter’s book. “We would just get gobs of food backstage and eat.”

The good times didn’t last at Chess, though. After more great tracks, such as the jaunty “Dynamite Lovin'” and the slow-building “Take Me for a Little While” (also recorded by Evie Sands, much to Ross’s chagrin), Ross started to suspect that she wasn’t being paid everything she was owed. According to Nadine Cohodas, author of the 2000 Chess history Spinning Blues Into Gold, Ross “disagreed with the notion that she shouldn’t concern herself with sales royalties because the record was really a means to better and more performing dates. ‘They sounded like I should be grateful because they put my name out there so I could work.'”

Ross left Chess in 1967 and signed with Carl Davis at the Brunswick label, producing quality songs such as the groovin’ “Mr. Sunshine (Where Is My Shadow),” cowritten by Davis and the Chi-Lites’ Eugene Record, and the gorgeously buoyant “Keep Your Chin Up.” Also in the late 60s, she released the stellar sweet soul tune “Showcase” via Jerry Butler’s Fountain label and the slightly psychedelic “Dr. Slap’s Man Is Born” (a fave of this author) for USA Records. Throughout the 1970s, Ross cut singles for a wide variety of small labels (GSF, Sedgrick) and a few larger ones (Capitol, Mercury), but despite their top-notch material and her enduringly supple voice, none of them succeeded commercially.

In 1979 she started recording for the Golden Ear label, an association that would last until the late 80s. During this era she often worked with producer and label founder James R. VanLeer, and in 1980 he produced and arranged her second proper full-length album, A New Beginning for Jackie Ross. Golden Ear also released two split LPs that paired Ross with bluesmen Little Milton and Bobby Rush, respectively, but A New Beginning is the record that collectors love—the cheapest copy on Discogs is currently selling for more than $475.

At around this time, Ross also began to benefit from the phenomenon called “Northern Soul.” Since the late 60s, record collectors in the north of England had been digging deeper and deeper into obscure American soul and throwing off-the-hook dance parties—they continue today, in fact, albeit without the same intensity. That UK scene loved string-soaked, midtempo grooves, and Ross had recorded plenty of those. She enjoyed a small career resurgence, and gave an interview and rerecorded two of her songs for the 1999 documentary The Strange World of Northern Soul, filmed by English songwriter, producer, DJ, and record hound Ian Levine.

Ross’s work has appeared on a staggering number of 60s soul and R&B compilations, but thankfully a few retrospectives have focused entirely on her own work, including 2005’s Selfish One (on Black Tulip Records), 2006’s Take the Weight Off Me (on Grapevine), and 2012’s Jerk & Twine: The Complete Chess Recordings (on Kent).

Ross has returned to singing gospel in Chicago churches, but she doesn’t stick to it exclusively—in 2010, for instance, she joined the R&B extravaganza at the Old Town School of Folk Music celebrating Syl Johnson’s Numero Group box set. “Her main thing (before the pandemic) has been designing and crafting dresses and doing other tailoring under the ‘Sew What? by Jackie’ name,” says soul scholar and Reader contributor Aaron Cohen. “She’s also been a nutritionist.” Here’s hoping that this living legend—who’s so much more than a one-hit wonder—can be coaxed back onto the stage when in-person concerts are safe for septuagenarians again!  v

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.

  • In a more sensible world, Jackie Ross would have lots of hits as big as “Selfish One.”
  • “Mr. Sunshine (Where Is My Shadow)” was written by Carl Davis of Brunswick Records and Eugene Record from the Chi-Lites.
  • Jackie Ross’s late-60s output also includes “Showcase,” released by Jerry Butler’s Foundation label.
  • “Dr. Slap’s Man Is Born” has a subtly psychedelic feel and an intro begging to be sampled.