RISK! Podcast - Live From Chicago!
Air Date: January 15, 2026
Host: Kevin Allison
Episode Theme: Live storytelling from Chicago—true, jaw-dropping stories with signature RISK! vulnerability, humor, and rawness.
Overview
This episode, recorded live in Chicago, features four captivating, uncensored personal stories. Host Kevin Allison curates an engaging lineup: Stephanie Douglas’s tale of her mom and a legendary prank, Shannon Cason’s hilarious misadventure in masculinity, Lily B.'s profound family revelation, and Jim Padar's behind-the-scenes police narrative. The episode explores themes of misunderstanding, embarrassment, trauma, resilience, and the messy humor of life.
Key Discussion Points & Story Breakdowns
1. Stephanie Douglas – “You Don’t Know Jack”
[04:54 – 17:24]
Story Highlights:
- Setting: High school, Stephanie’s mother as a teacher’s aide.
- Prank Origins: A student’s name “Jack Mehoff” (a pun for “jack me off”) is broadcast over school announcements.
- Stephanie’s mother, earnest and oblivious to the joke, becomes convinced a bullied, disabled student is being mocked and abused.
- She interrogates students and faculty, escalating her concern and is met with complicit joking responses (students and teachers keeping up the ruse).
- She winds up in the principal’s office, finally learns the truth from Ms. Pryor, and leaves, mortified and indignant.
- At home, Stephanie must explain the crude pun to her mom, who blames Ms. Pryor for corrupting her daughter.
- In classic RISK! fashion, Stephanie closes with humor about her mother’s well-meaning but doomed savior complex.
Notable Quotes & Moments:
- “All she had heard was an innocent boy's name read, and then seen a room full of cruel teenagers cackling and cackling and cackling.” (Stephanie Douglas, 05:11)
- “Who is this boy? Why is everyone laughing when they say his name?” (Stephanie Douglas, 05:36)
- “She knew that this was serious. Bullying is not something that we laugh about.” (Stephanie Douglas, 07:30)
- “Jack Mehoff... Like jerk me off, it's a pun.” (Stephanie Douglas & Ms. Pryor, 12:51)
- “Ms. Pryor, I had no idea you were such a whore.” (Stephanie Douglas, channeling her mother's reaction, 13:02)
- “For every oft beaten, bullied, one eyed boy out there... your protector is out there and she is watching and waiting.” (Stephanie Douglas, 17:00)
2. Shannon Cason – “Jelquing: A Cautionary Tale”
[17:53 – 31:36]
Story Highlights:
- Premise: Humorous journey of insecurity about penis size, kicked off with a story about a consensual “train” (group sex) in his past and comparison between him and a friend.
- Research & Experimentation: After watching porn, curiosity leads him to Google “ways to get a bigger dick.” He tries jelqing (an internet-found exercise), ignoring instructions to warm up, and feels pain.
- Domino Effect: Same day, his friend drops by, leading to a greasy-handed arm wrestling match. Later, his penis becomes totally unresponsive, prompting anxiety.
- Downward Spiral: Days pass with “lifeless” genitals; no sexual or random arousal, major anxiety, and abysmal work mood.
- Comic Resolution: At a Halloween party with his wife and ex, a suggestive moment and “a gush” miraculously revives him. Later, a dull pain persists, prompting him to file a work injury report—he is diagnosed with a double inguinal hernia and surgery is covered by work insurance.
- Takeaway: Don’t mess with what you’ve got.
Notable Quotes & Moments:
- “If we get another guy... that would be, like, closer to a train. I'm not running anywhere near close to a train on my wife.” (Shannon Cason, 18:06)
- “You gotta be in a desperate place to put some weights on your dick, you know?” (19:45)
- “I never seen my dick look this lifeless in my life.” (Shannon Cason, 24:36)
- “...if you have any problems with your dick, be happy with what you got. Don't fuck around with it because you could end up losing, you know, the little bit you have.” (Shannon Cason, 31:28)
3. Lily B. – “Morena, Por Favor”
[32:07 – 50:11]
Story Highlights:
- Opening Memory: Five years old in 1983, Lily witnesses her tiny, religious mom furiously throwing her father’s things out after a mysterious argument.
- Eleven Years of Misdirected Blame: No one will tell Lily what happened, so she blames her mother for driving her loving dad away.
- Family Reunion & Truths Uncovered: At age sixteen, at her grandmother’s funeral, her aunt (drunk and unfiltered) fills her in. Her mother had suspected her dad was cheating, set a trap by hiding in their van, and caught him having sex with another woman literally above her hiding place.
- Lily’s Reaction: Overwhelmed, guilty for years of misjudged anger, Lily has a heart-to-heart with her mom, who calmly confirms the story and insists Lily love her dad for who he is—a father, not a husband.
- Closing Reflection: Lily learns that her mother protected her view of men (and Lily’s father) to spare her bitterness and raise her differently. Lily recognizes her mother's sacrifice and strength.
Notable Quotes & Moments:
- “My mom's religious and she's very patient and understanding and God will look out and he'll take care of us... So to see this woman on a mission, I didn't say anything.” (Lily B., 33:09)
- “She shimmies her way in there with her head from facing the front of the car... thinking, 'I’m gonna catch this motherfucker.'” (Lily B., 39:23)
- “Had this been me in the back of this van. Crime of passion. I swear would have been on the news that day.” (Lily B., 41:11)
- “Because again, it could not have been me. It could not have been. And two was that she did it and did everything for us, for me.” (Lily B., 48:56)
- “You are going to love your father because that’s your father, not your husband... that's my cross to bear, not yours.” (Lily B., relaying her mother's wisdom, 47:12)
4. Jim Padar – “Homicide: The Case of Larry Wiggins”
[51:41 – 67:16]
Story Highlights:
- Backdrop: Summer 1975, Chicago. Padar and his partner answer a call to a stabbing in a notoriously dangerous housing project.
- On Scene: They find a crowd gathered around a young man (Larry Wiggins) spurting blood from a carotid wound. Padar applies pressure to keep Larry alive while his partner fetches supplies and calls for an ambulance.
- Emergency Ordeal: Paramedics wrap Padar’s hand to the wound—he stays literally attached during a harrowing ambulance ride and throughout the chaotic trauma ward experience.
- Aftermath: Despite incredible efforts, Larry dies days later. Padar is thanked by Larry’s mother, is told he made it possible for the family to say goodbye, despite not ultimately “saving” him.
- Community & Closure: Both mothers—Larry’s and “Pookie’s” (the perpetrator)—bring Pookie to the police to surrender, a demonstration of maternal fortitude in the face of tragedy.
- Emotional Resonance: Padar reflects on the hollow victory of “solving” a case while recognizing the deeper, painful realities families endure.
Notable Quotes & Moments:
- “There was a crowd there... but they were strangely quiet, one of those situations that makes a cop's hair stand up.” (Jim Padar, 52:11)
- “The only way I could describe the expression on his face is what I would call primal fear.” (Jim Padar, 54:01)
- “Don't fuck with me or I'll move my fingers.” (joking with paramedics, 55:25)
- “You gave us a chance to tell him we loved him and say goodbye.” (Larry’s mother’s gratitude, 61:55)
- “I should have felt good about it... But the victory to me was hollow because I hadn't really saved anybody.” (Jim Padar, 66:24)
Memorable Moments & Quotes (With Timestamps)
-
Stephanie Douglas:
- “Who is this boy? Why is everyone laughing when they say his name?” [05:36]
- “Ms. Pryor, I had no idea you were such a whore.” [13:02]
-
Shannon Cason:
- “You gotta be in a desperate place to put some weights on your dick, you know?” [19:45]
- “I never seen my dick look this lifeless in my life.” [24:36]
- “Don’t fuck around with it because you could end up losing, you know, the little bit you have.” [31:28]
-
Lily B.:
- “My mom’s religious and she’s very patient and understanding and God will look out and he’ll take care of us... So to see this woman on a mission, I didn’t say anything.” [33:09]
- “Had this been me in the back of this van... Crime of passion.” [41:11]
- “That’s your father, not your husband... that's my cross to bear, not yours.” [47:12]
- “My mom is a badass motherfucker, man.” [48:53]
-
Jim Padar:
- “The only way I could describe the expression on his face is what I would call primal fear.” [54:01]
- “Don’t fuck with me or I’ll move my fingers.” [55:25]
- “You gave us a chance to tell him we loved him and say goodbye.” [61:55]
- “The victory to me was hollow because I hadn’t really saved anybody.” [66:24]
Timestamps: Segment Guide
- [04:54] — Stephanie Douglas: "You Don’t Know Jack"
- [17:53] — Shannon Cason: "Jelquing: A Cautionary Tale"
- [32:07] — Lily B.: "Morena, Por Favor"
- [51:41] — Jim Padar: “Homicide: The Case of Larry Wiggins”
Tone and Style
- Stephanie Douglas: Wry, exasperated humor; warm family storytelling with a satirical edge.
- Shannon Cason: Playful, self-deprecating, hilarious; open about embarrassment and masculinity.
- Lily B.: Heartfelt, dramatic; mixes Spanish and English; emotionally charged but grounded in empathy.
- Jim Padar: Gritty, matter-of-fact yet compassionate; veteran police voice gives realism and warmth.
Conclusion
Live From Chicago! is a classic RISK! episode—funny, vulnerable, and raw. The storytellers let their guards down to share stories that are embarrassing, shocking, and deeply human. The episode highlights how much we are shaped by misunderstandings, secrets, and the ways we try, fail, and sometimes succeed in protecting ourselves and others.
Risk’s fifth year kicks off with candid, surprising, and moving stories—inviting listeners, as ever, to take a risk themselves.