City Cast Chicago Superlatives

To close out our “1,000 Things We Love About Chicago” week, we’re sharing just some of our favorites from our over 1,000 podcast episodes. Enjoy our City Cast Chicago superlatives!

🥲 Most Surprising Tearjerker

Looking for a good cry? Check out the episode where host Jacoby Cochran took a tour of Claudia Galeno-Sanchez’s butterfly sanctuary in Pilsen. Her home garden is built to help monarch butterflies on their way to Mexico. She says their journey mirrors her own migration story.

📚 Best Chicago Book List

This one is for the bookworms. In this episode, Jacoby chatted with Chicago writer, scholar, and cultural organizer Eve Ewing to curate the best Chicago reading list.

🍷 Best Drink Guide

If you’re on the hunt for a good drink, check out our approachable guide to wine. Jacoby spoke to Chasity Cooper, author of “Wine Convo Generator,” about where to get a great glass of wine in the Windy City and how to sound like a wine expert (even when you’re not).

🖤 Most Important Voices

Producer Michelle Navarro attended a workshop organized by The Trace, where family members and friends who lost loved ones to gun violence came together to share their personal stories. Michelle took us there to listen to participants’ experiences and joined Jacoby to discuss what she learned.

🔊 Best Sounds

Grab your cowboy boots, we are going back to the South Side Rodeo. Listen for a whole lot of yee-haws and horse neighing!

🐦 Best Animal Story

Calling all of the City Cast Chicago animal lovers — this episode will make you stop calling pigeons “rats with wings.” Jacoby and Michelle visit the Great Lake Pigeon Rescue to learn why these animals need more care.

📝 Most Useful Political Guide

This podcast delves into the question of who holds the most political power in Chicago. Jacoby is joined by the Tribune's A.D. Quig and WCIU TV host Brandon Pope to unpack the city's political hierarchy.

🐂 Most Famous Interview Guest

Benny the Bull. Need we say more? (Sorry Stephen Colbert …)

💭 Best Walk Down Memory Lane

Come with us to the MLK Roller Skating and Bowling Center in Auburn Gresham with Chicago legend Theresa “Sweet T” Ferrell, aka Jacoby’s mother.

📜 Best History Lesson

Looking to brush up on your Chicago history? WBEZ reporter Natalie Moore and former Cabrini-Green resident and housing activist Willie “J.R.” Fleming chat with Jacoby about the history of the 23 high-rise towers and adjacent row houses of the storied public housing development.

🥶 Coldest Article

As for the favorite newsletter segments? I think this one I wrote last month, might be the coldest article on our list.