The Flip Side: Where Chicago Rocked

Anyone who’s ever wondered about brick-and-mortar record stores —a rarity in 2025— will immediately see the appeal of The Flip Side: Where Chicago Rocked. Written by record store owners Carl & Larry Rosenbaum with Ken Churilla, the two brothers tell everything there is to tell about their decades-long run of Flip Side stores all over Chicago. Whether you’ve heard of that particular record store or been within even a thousand miles of Chicago isn’t important — it’s not required to enjoy this wonderful portal to the past.

Surprisingly, the decision by the two brothers to jump into the music business was a toss-up between that, a dry-cleaning store, or a hot dog stand. They settled on a record store with a shrug and little experience, but they had a smart idea to sell concert tickets from their store. Doing so eased congestion at local department stores and sent music fans directly to their doors. Concertgoers would crowd the building hours in advance (sometimes days!), hoping to get the best seats at the next show and end up buying records in the process. Before long, Flip Side would become a local icon, leading to the opening of more stores, iconic merchandise (you can still find their branded t-shirts), and consistent radio promotion. It’s hard to look back with clarity and imagine anything other than online music stores pushing brick-and-mortar shops out of business, but as the Rosenbaums tell it, it was actually big box stores like Best Buy who made things difficult by selling albums (with near infinite stock) at just above wholesale.

And fascinating as that journey is, the record stores are just the tip of the proverbial iceberg. The Rosenbaums eventually gravitate to concert promotion, earning them larger exposure in the music business and all the insanity that comes with it. In the midst of their luncheons with Celine Dion, meetings with Howie Mandell and Evel Knievel, and in-store promotions with legendary acts like Foghat and Cheap Trick, you’ll also learn about their run-ins with the mob, the FBI, Chicago’s unions, and the law. All these ordeals are conveyed not with sadness but good humor and nostalgia.

Co-Author Ken Churilla takes a fun approach to The Flip Side: Where Chicago Rocked — the entire book is presented as a filmed documentary. Carl and Larry take turns sharing stories about their experiences, and readers are occasionally treated to vignettes from employees, family members, or business partners. The last section of the book reads like an extended eulogy for the business from their kids and spouses. You’ll wish you were a part of Flip Side, if only as a music fan, thumbing through their records on W. Foster Avenue back in 1968.