Kill Tony Podcast – Episode #757 Summary

Date: February 24, 2026
Location: Comedy Mothership, Austin, Texas
Featured Guests: Matt Rife, Adam Ray (as “Jeremy”), plus recurring and new comics
Hosts/Band: Tony Hinchcliffe (A), Brian Redban (B), plus in-house band

Overview & Theme

This episode of Kill Tony is a classic blend of chaotic live standup auditions, roasts, and raw, unpredictable interviews—turned up to 11 by a cast of oddball comics and unscripted audience interactions. The show features hot comedic talent Matt Rife, the persona “Jeremy” (impersonated by Adam Ray), and a wild carousel of amateur and regular performers, ranging from debut standup attempts to bizarre stalkers and costumed clowns. Themes include surviving bombing on stage, confessional moments (sobriety, cancer survival, strange hobbies), and the ever-present possibility of absolutely anything happening in real time—sometimes uncomfortably so.

Key Segments & Highlights

1. Opening: Welcoming Matt Rife and Setting the Tone

• [01:34] Tony builds anticipation for the show, praising Matt Rife's rise to stardom and their decade-plus friendship.
• Matt Rife takes the stage to massive applause, joking with Tony about mutual admiration:
  • Tony: “You are just a specimen. Charming, good looking … I’m in heaven here tonight.”
  • Matt: “Stop.”
  • Tony: “You’re damn right.”

2. William Montgomery’s Feature Set

• [04:55 – 13:44]
• William, a Kill Tony staple, opens with intentionally rambling, surreal humor covering lost scooters, Blippi conspiracies, email spam, and traveling with kids’ shows for “comfort.”
  • Notable quote: “Give Epstein credit where credit is due. The guy had zero spam in his inbox...” – William [04:55]
• Deep-dive into why William binge-watches Blippi, ongoing Blippi actor changes, and William’s attachment to kid stuff and rowing for mental health.

3. Comic Auditions ("Bucket Pulls") and Interviews

Monique Jones

• [14:11 – 21:44]
• Returns after 8 years: talks beating breast cancer, being a massage therapist in LA, connections to Paul Rudd, Adam Scott, and Oliver Stone, and the role of hormone-blockers in her life.

Jeremy (Adam Ray)

• [24:29 – 35:19]
• Jeremy delivers a punchy, high-energy set filled with self-deprecating humor, pop culture riffs, and wild props from his fanny pack (space food, toy snakes, Dr. Pepper Tic Tacs).
  • Notable quote: “I used to ride scooters in Austin. But then I got hurt when a bunch of kids pointed at my helmet and called me a pussy. Now I take the bus.” – Jeremy [27:00]
  • Extended after-interview includes a deep dive through his oddball fanny pack for comic effect (“I'm a snake guy…”), which brings huge laughs from the crowd and panel.

Anthony Fink

• [36:59 – 46:36]
• Bread and yeast-infection puns, admits to taking standup breaks due to work at Lockheed Martin, reveals he can “bomb in six different languages,” and discusses details of a sex tape with his black girlfriend: “Way more cheeks. It’s warmer.” [43:04]

J.P. Leonard

• [47:14 – 54:43]
• Stories from Cajun Louisiana, Popeyes Buffet, 23 years in education/special ed, weight loss, and Eeyore-themed bedroom role play.
  • Notable exchange:
    • Jeremy: “Any of the kids ever try to fight you?”
    • JP: “[...] I was the cool teacher.”

Kyle

• [55:48 – 62:20]
• Raw, anxious first-timer with “woodland hermit” vibes, lives alone in a cabin built by his dad, has no job, does bird calls (“just a general call to all birds”).
  • Quote: “My life's too tragic to be taken seriously by the way I look.” [57:27]

Sir Winston Pickles

• [64:48 – 71:43]
• British clown with pitch-black jokes (“I've been sponsoring this little guy in Africa for the last three years…last March, my credit card expired. So he's dead.” [65:06])
• Discusses clown persona, refuses birthday party requests, and dark worldview.

Hey Bullstad

• [72:25 – 83:55]
• Newly sober at 51, stories of $200k rehab and AA, awkward motivational speaker gig, and former wild-living exploits.
  • Tony’s roast: “There’s nothing interesting about that man whatsoever on planet Earth.”

4. Wild Card Segment: Real-Time Stalking Drama

• Ryan Dorr ([88:03 – 102:44])
• Delivers set about spending on weed and escorts, then confesses he drove 25 hours to meet comedian Kim Congdon after becoming “obsessed” with her. Attempts calling her live, admits to sending flowers and a ring.
  • Notable moment: Tony, Matt, and Lindsay break down the situation for crowd safety and reality check, with Tony labeling it “one of the scariest things in the history of the show.”

5. Regulars and Closers:

Drew Nickens

• [103:33 – 110:12]
• Celebrates first sex in 18 months, jokes about lovers with mullets, and WWE matches.
  • Tony: “Drew, do you like the show Blippi?”
  • Drew: “Fuck yeah. [...] Bring back my Blippi.” [107:49]
• Ends with riffing on Black History Month: “I went to Ross five times this week.”

Thomas La Mountain [115:32 – 120:08]

• Fast-sex-with-old-women jokes, discusses a breakup where rescuing his Lego set was the high emotional point.

Dedrick Flynn (show closer)

• [121:04 – 127:02]
• Extended, rapid-fire bit about Frontier Airlines, racial profiling, bag fees, and shooting dice/selling snacks on the plane.
  • “Worst set of the night is better than no set.”
  • Flirts with Matt Rife, roasts the crowd, and closes with his signature energy.

Notable Quotes & Memorable Moments

• “[About Blippi:] It makes me smile, it makes me laugh. I love it. It’s better than Toddlers & Tiaras.” – William [07:00]
• “You can bomb in six different languages.” — Tony to Anthony Fink [40:02]
• “I’m a snake guy.” — Jeremy, after pulling animal toys from his fanny pack [31:23]
• “All I’ve ever wanted is to be a bellhop…My dad was a bellhop, my grandpa was a bellhop.” – Thomas La Mountain [117:51]
• “Every other show in the world… has been predetermined and was planned before you ever saw it. Except for this moment…” – Tony on the live stalker moment [93:47]

Timestamps for Important Segments

| Time | Segment/Highlight | |-----------|--------------------------------------------------------| | 01:34 | Opening remarks, Matt Rife intro | | 04:55 | William Montgomery’s set & Blippi talk | | 14:11 | Monique Jones: Cancer survival, massage therapy, 2018 | | 24:29 | Jeremy’s set, fanny pack props, joins panel | | 36:59 | Anthony Fink: Bread jokes, sex tape, languages | | 47:14 | JP Leonard: Special ed, Popeyes Buffet, Eeyore roleplay| | 55:48 | Kyle: First time, life in woods, bird calls | | 64:48 | Sir Winston Pickles: Grim clown, dark gags | | 72:25 | Hey Bullstad: Rehab, AA, motivational speaker | | 88:03 | Ryan Dorr: Stalking Kim Congdon, live call attempt | | 103:33 | Drew Nickens: Sex after 18 months, Blippi, Reddit beef | | 115:32 | Thomas La Mountain: Old-lady sex, Lego breakup | | 121:04 | Dedrick Flynn: Rants on Frontier Airlines, closing set |

Episode Tone & Takeaways

This episode oscillated between playful chaos, authentic vulnerability, and edgy, sometimes cringeworthy moments. The inclusion of a real-time stalker/intervention segment was perhaps the most uncomfortably authentic moment in Kill Tony history—showcasing, as Tony said, the unpredictable, live-wire nature of the show versus any “planned” comedy format.

Amid the anarchy, strong performances and comedic camaraderie shone through—especially from Matt Rife, Jeremy/Adam Ray, William Montgomery, Sir Winston Pickles, and Dedrick Flynn, showing the resilience and rapid-for-fire wit that anchors the show.

Final Notes

• Best Sets: Dedrick Flynn (closer), Sir Winston Pickles (clown), William Montgomery’s surreal opener
• Wildest Interview: Ryan Dorr’s awkward obsession with Kim Congdon
• Recurring Jokes: Blippi, snacks/props in bags, weird breakups and sex tapes, “is it real or is that cum?” street game

In sum:
A quintessentially unfiltered, unpredictable, and laugh-packed Kill Tony episode—blending earnest personal stories, misfit comedy, and slices of live show madness—with Matt Rife and Jeremy (Adam Ray) as top-tier comedic foils for the chaos surrounding them.