Romantic Comedies in Chicago: A Conversation
- Mar 20
- 1 min read
In an interview with Donte Diesel Williams, I explore why Chicago shines in romantic comedies, how the city shapes cinematic storytelling, and my own journey from film professor to Chicago Movie Tours founder.
I had the pleasure of sitting down with Donte Diesel Williams—TV news photojournalist, filmmaker, and Chicago film historian—for his YouTube series The Chicago Film Experience.
In our 23-minute conversation, Donte asked some great questions:
What attracted you to the film landscape of Chicago?
Why do so many romantic comedies choose this city?
Before you moved here, were you into Chicago films?
We explore all of this and more, diving into romantic comedies filmed in Chicago—from While You Were Sleeping and My Best Friend’s Wedding to Groundhog Day and Love Jones—while also unpacking the blurry line between rom-com and screwball comedy.
We talk about why Chicago works as a backdrop for love stories, how the city shapes character and narrative, and what makes certain films—like The Blues Brothers and Ferris Bueller’s Day Off—feel like true cinematic love letters to the city.
Along the way, I share my own path from teaching Shakespeare and Gene Kelly in the university classroom to running Chicago Movie Tours.
If you enjoy thinking about genre, film history, and Chicago onscreen, I believe you’ll enjoy our full conversation—which you can watch below.
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