• OTL #1,004: Wage theft in Illinois, A look at the state's fiscal health
    Jan 10 2026

    Mike Stephen talks to Injustice Watch senior investigative reporter Alejandra Cancino to learn how wage theft of workers continues in Illinois and then gets the lowdown on a new report that examines the fiscal health of the state from Civic Federation senior policy advisor Paula Worthington.

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    40 mins
  • OTL #1,003: A look back at 2025
    Jan 3 2026

    Mike Stephen takes a look back at some highlights of the show from 2025. Happy New Year from your friends at Outside the Loop!

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    42 mins
  • OTL #1,002: A college in degree in Illinois can go a long way, The Secret History of Kitty Haywood
    Dec 27 2025

    Mike Stephen discusses a new report that shows a college degree is the most promising path to a good job in Illinois with Chalkbeat Chicago bureau chief Becky Vevea and then discovers the Secret History of 20th century soul vocalist Kitty Haywood.

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    38 mins
  • OTL #1,001: Straight Outta Skokie, Creative Cypher's Chicago entertainment ecosystem
    Dec 20 2025

    Mike Stephen talks to Al Krockey, the author of a new book about coming of age in the 1960s and 70s in Skokie and Chicago called Straight Outta Skokie, and then learns about the plans Creative Cypher has for building an entertainment ecosystem in Chicago from founder Troy Pryor and interim president Cindy Beasley.

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    39 mins
  • OTL #1,000: The 1,000th episode live from Fitzgerald's!
    Dec 13 2025

    Mike Stephen hosts his 1,000th episode of Outside the Loop at Fitzgerald's Nightclub!

    Guests include:

    -Will Duncan and Jess King, owners of Fitzgerald's

    -Dominic Pacyga, professor emeritus of history at Columbia College Chicago and author of Clout City

    -Steve Krakow (aka: Plastic Crimewave), local musician and author of The Secret History of Chicago Music

    -Holley Brandchaft-White and Genia Yovankin, founders of SHFT Behavioral Health

    -Surprise guest: Andy "The Count" Hermann, co-founder and former producer of Outside the Loop and current producer at Nebraska Public Media

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    1 hr and 30 mins
  • OTL #999: The new editor in chief of the Chicago Reader, How are CPS students doing after they graduate?, New Holiday music from Kevin Brown
    Dec 6 2025

    Mike Stephen talks to Sarah Conway, the new editor in chief of the Chicago Reader, about the future of the paper, discusses Chicago Public Schools student educational attainment post-graduation with the To&Through Project director of data and research Alexandra Usher, and gets the lowdown on new Holiday music from local guitarist Kevin Brown.

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    45 mins
  • OTL #998: Rethinking housing in Chicago and beyond, The Robert Townsend Pop-Up Film Fest, Public transit reliability
    Nov 29 2025

    Mike Stephen learns about a new exhibit at the National Public Housing Museum from UIC architecture professor Alexander Eisenschmidt, chats with actor and director Robert Townsend about his upcoming Chicago pop-up film fest, and re-visits a segment on local public transit reliability.

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    38 mins
  • OTL #997: Local journalism ethics in a time of ICE occupation, New music from These Peaches, The Haitian American Museum of Chicago
    Nov 22 2025

    Mike Stephen discusses the role of local journalists during a time of local ICE occupation with McKinley Park News publisher Justin Kerr, gets the lowdown on new music from the local band These Peaches from frontman Rich Klevgard, and learns about the significance of the Haitian American Museum of Chicago from founder and CEO Elsie Hernandez.

    AND...come out to Fitzgerald's at 6615 W. Roosevelt Rd. in Berwyn on Saturday, November 22, at 3:00 p.m. for the Outside the Loop 1,000th episode taping! It's a FREE event, but you need to RSVP using this link.

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    39 mins