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.

I’m not going to lie—for some reason, the story of the Chicago Loop has been tough for me to piece together. It’s beyond me how there could be so little information on the Web about a band that produced a decent-size hit and included two members who were already well-known at the time, but I’ll do my best by this important Windy City group.

The core of the Chicago Loop were former folk singers Judy Novy (sometimes billed incorrectly as “Navy”) and Bob Slawson. Novy was born in Chicago in January 1946 and formed a vocal duo with her brother Len that released its debut 45 in 1961. On that collectible single, “I’m Leaving Town, Baby” b/w “Willy Nilly Joe” (released by Chicago label Deer Records), Len & Judy planted themselves firmly in swingin’ rockabilly territory. But by 1965 they’d hopped on the folk-boom bandwagon for an LP on Prestige called Folk Songs/Sweet & Bittersweet.

Despite a painfully wholesome-looking cover, the album was surprisingly progressive for its time. It includes a spaced-out version of “In My Time of Dying” that prefigures mainstream psychedelia by a few years, and the musicians involved include George Edwards (later of H.P. Lovecraft) on 12-string guitar and the underrated Dwain Story (formerly of the Knob Lick Upper 10,000) on guitar and Dobro.

The duo gigged around the midwest, frequently visiting Michigan, and after their split in the mid-60s I can find little further evidence of Len’s career—in 1969 he did make an interesting solo LP for Atco, which mixes up weird country-rock and straightforward crooner pop.

In 1966, Judy Novy joined a band called Time with vocalist-guitarist Bob Slawson and pianist Barry Goldberg, the latter of whom had recently found fame sitting in with the Butterfield Blues Band when they backed Bob Dylan for his “heretically electric” appearance at the 1965 Newport Folk Festival. Slawson had been in folk groups such as the Almanac Singers, and in ’65 he’d played harmonica for Shel Silverstein’s 1966 LP “I’m So Good That I Don’t Have to Brag!” Shel Silverstein Sings His Songs. Time supposedly recorded a six-song demo (though by then they may have changed their name to the Chicago Loop), but the tapes have never turned up.

Butterfield Blues Band guitarist Mike Bloomfield (later of many a “super session”) might have played on that demo too, and he was definitely in the band’s orbit—he would soon contribute to a tune on their debut as the Chicago Loop. In 1966 their lineup grew to include bassist Carmine Riale and drummer John Siomos, and they worked with producer Bob Crewe (most famous for his work with the Four Seasons) for two singles on Crewe’s DynoVoice label. Bloomfield’s smokin’ guitar leads appeared on the A side of the first 45, “(When She Needs Good Lovin’) She Comes to Me,” which hit number 37 on the Billboard Hot 100.

The single also earned releases in the UK, Canada, France, the Netherlands, and Brazil—it represented the most sales success anyone in the band had seen at that point. The Chicago Loop’s work with Crewe also produced a fuzzed-out, punky cover of Simon & Garfunkel’s “Richard Cory,” released early in 1967, but by then Bloomfield had left, replaced by John Savanno. “Richard Cory” had just been covered by Van Morrison’s Them, and the Chicago Loop version hit number 98 on the Canadian charts but did nothing elsewhere.

Bloomfield moved to San Francisco, soon followed by Goldberg, to put together his band the Electric Flag. Slawson assembled a new Chicago Loop lineup and signed the group to Mercury Records. He and Novy were the only original members remaining—for their stint on Mercury, the other members included keyboardist Roy Hope, drummer P.J. Bailey, bassist George Miller, and a few different guitarists. The 1967 single “Saved” b/w “Can’t Find the Words” was a nice slab of garage pop, but it tanked. The Chicago Loop’s final release—and my favorite of theirs—is the wildly psychedelic 1968 single “Technicolor Thursday” b/w “Beginning at the End.” These catchy tunes, steeped in strange backward effects, spacey atmospherics, and guitar scuzz, were written by an outside songwriter, Christopher Welch—who also cowrote material later performed by Sonny & Cher and the Brady Bunch. The 45’s sound was right in line with plenty of music that charted in 1968, but it too failed, spelling the end of the Chicago Loop.

By then Crewe had already recruited Riale, Slawson, and Siomos to form the rhythm section of a horn-heavy ten-piece band backing bluesy rocker Mitch Ryder of “Devil With a Blue Dress On” fame—in February 1967 they’d first hit the road as the Mitch Ryder Show. Riale is credited as producer and arranger for a 1975 single, “She’s a Stone Freak,” by a funky band called Frog, and both he and Novy are credited as producers or sound technicians on a rare 12-inch released by folky, psychedelic “world music” group Annapurna in 1976. Bloomfield and Goldberg went on to have high-profile musical careers, of course, but I can’t track any other veterans of the Chicago Loop past the late 70s—the rest of their story remains a delicious mystery.  v

The radio version of the Secret History of Chicago Music airs on Outside the Loop on WGN Radio 720 AM, Saturdays at 6 AM with host Mike Stephen. Past shows are archived here.

  • The Chicago Loop’s lone hit, from 1966
  • The Chicago Loop’s 1967 cover of Simon & Garfunkel’s “Richard Cory”
  • Judy Novy of the Chicago Loop released this borderline psychedelic version of “In My Time of Dying” in a duo with her brother Len in 1965.