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.

Rose named the band the Five Bucks, and they made business cards mimicking (you guessed it) $5 bills. They started playing frat parties, mixing Beatles tunes and other hits of the day with their own early attempts at original songs. The whole band moved to Chicago at the end of the school year in spring 1966, intending to spend the summer playing around the city—Rose and Hearn’s families lived in Chicagoland, so it wasn’t the huge leap it might’ve been. Hearn’s girlfriend’s father was Windy City real estate tycoon Jerry Wexler (not the big Atlantic Records guy, but brother to famed cinematographer Haskell Wexler), and he helped the Five Bucks get an audition with the Afton label.

At around that time, the band released their final single as the Five Bucks through a somewhat bigger label, USA Records. Now hard to find, it includes the jazzy, harmony-soaked “Breath of Time.” In fall 1968, the band’s managers secured them an “unplugged” audition for Bill Traut of famed Chicago rock label Dunwich Records, who liked what he saw—he figured the Five Bucks could be his own version of breezy, hit-making California pop band the Association (“Along Comes Mary,” “Cherish”). The Association also had an Asian member, Larry Ramos (a Filipino American born in Hawaii), so Tom made the questionable choice to adopt a Hawaiian stage persona—though thankfully it was short-lived.

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.