Mike Stephen discusses the decrease in public school students in Illinois with Chalkbeat Chicago's Samantha Smylie, learns about Black organizing pre-Civil War in Illinois with Northwestern University history professor Kate Masur, and discovers the Secret History of local saxman J.T. Brown.

Mike Stephen learns about the new expansion of Chicago literacy nonprofit Open Books from executive director Eric Johnson, learns how ChicagoJazz.com is back in full swing and delivering new local music coverage from its founder Mike Jeffers, and discovers new local tunes from musician Daniel Gunderson.

Mike Stephen discusses the impact and significance of the Chicago Public Library over the last 150 years with library commissioner Chris Brown and then discovers the Secret History of local blues vocalist and drummer Ms. Johnnie Mae Dunson.

Mike Stephen talks to former Chicago Tribune reporter Josh Noel about his decision to leave the paper and then learns about local train crawls from Scott Presslak, the founder of Yard Social.

Mike Stephen learns about The Answer Inc, a local organization that helps those with disabilities, from founder and CEO Debra Vines, gets the lowdown on the best Led Zeppelin tribute band from "Bobby Plant 2" (aka: Bruce Lamont), and discovers the Secret History of blues guitar master John Primer.

Mike Stephen airs a few big show conversations from 2022.  Happy New Year from your friends at Outside the Loop!

Mike Stephen gets an update on the impact of TIF districts on Chicago neighborhoods over the past year with Tom Tresser, co-founder of The CivicLab, and then re-airs a conversation with Illinois native Kevin Jakubowski, the screenwriter of the Holiday film 8-Bit Christmas.

Mike Stephen learns how pollution is impacting McKinley Park from Anthony Moser, board president of Neighbors for Environmental Justice, discusses the creation of the first Green Dining District in Illinois with Ravi Parakkat, Oak Park trustee and founder of Takeout 25, and discovers the Secret History of 1960s soul singer Jo Ann Garrett.

Mike Stephen discusses the “We Will Chicago” plan and its criticisms with City Bureau reporters Jerrel Floyd and India Daniels, talks to local photographer Marty Perez about his 40 years of music photography and his new book called Kill a Punk For Rock & Roll: 1976-2019 Photographs, and chats with Peter Moore, artistic director at Steep Theatre, about that theater company's new grant from the City of Chicago.

Mike Stephen learns about the fascinating history of Kaskaskia, IL, from Illinois Humanities' Matt Meacham and then dives into the story of the 1980s-era metal band Witchslayer.