Comedy Bang Bang: Bonus Bang – 2019 Tour, Chicago

Date: January 29, 2026
Host: Scott Aukerman
Guests/Characters: Jason Mantzoukas, Paul F. Tompkins (as Alimony Tony), Lauren Lapkus (as Big Sue), Carl Tart (as The Chief)

Episode Overview

This live episode, recorded at the historic Chicago Theater during the 2019 Comedy Bang Bang tour, is a classic in the show's storied history. Host Scott Aukerman corrals an all-star lineup of improvisers – Jason Mantzoukas, Paul F. Tompkins, Lauren Lapkus, and Carl Tart – for a fast-paced, character-driven night of surreal, surreal comedy and absurd storytelling.

The episode centers around the beloved character Alimony Tony (Paul F. Tompkins), a divorcee who genuinely loves paying alimony, alongside a menagerie of oddballs: Big Sue (Lauren Lapkus), who sells soaking-wet carpets out of her own squalid shop, and The Chief (Carl Tart), a law enforcer on a lifelong quest to capture Carmen Sandiego.

Through high-energy banter, audience interaction, improvised songs, and wild sketches, the group explores topics ranging from deathbed confessions to the secret lives of billionaires, with irrepressible tangents, inside jokes, and Chicago-centric flavor.

Key Discussion Points & Memorable Segments

1. Chicago Theater Memories & Show Kickoff

• [04:15] Scott reminisces about breaking his foot in Chicago during a past CBB tour, setting the slapstick, irreverent tone.
• [09:47] Mantzoukas is welcomed as quasi-cohost, immediately riffing on Chicago’s “gorgeous hunks and honeys” and razzing the audience:

  “Scott said upstairs, I bet it's gonna be a lot of uggos. And I said, buddy... this audience is top to bottom, t to B. Gorgeous hunks and honeys.” – Jason Mantzoukas [10:04]

• Banter quickly devolves into bits about death preferences and “haunting” the theater, blending dark humor with playful celebration of the city.

2. Existential Comedy: Death, Legacy & Podcasting

• [13:00] Conversation on “ideal ways to die”:

  “I would like to die while falling from a great height. Really, in the midst of it.” – Jason Mantzoukas [13:00] “If I had to die, and I sincerely hope I don't... I would pick [the Chicago Theater] as my number one place.” – Scott Aukerman [11:30]

• Existential anxieties are met with comic clinical detachment (“Meat in the ground!... Meat and potatoes." – Scott & Jason [17:35-17:39]).
• Jason jokes about wanting the audience present at his deathbed, with more deadpan:

  “These are some of my dearest friends.” – Jason Mantzoukas [15:53]

3. Introducing Alimony Tony

• [25:23] Paul F. Tompkins emerges as Alimony Tony:

  “...Married seven times. Please welcome Alimony Tony!” – Scott Aukerman [25:28]

• Tony is fiercely proud of his divorces:

  “I love to pay alimony so much, so my nickname is Alimony Tony.” – Alimony Tony [28:14]

• Tony shares:
  • He’s “child-free” and “childless,” unable to procreate ("Turns out to be grapefruit juice. Drank too much as a child." [29:55–30:05])
  • Ruthlessly up front with romantic prospects about both his infertility and enthusiasm for alimony (“...before the waiter even comes over, I say, look, let me get this out of the way. If you're looking for children, you've got to look somewhere else..." [31:46])
  • Keeps an ever-updated closet of wife clothes, takes pride in customizing wardrobes for each spouse (“I have in my home a closet full of clothes for a potential wife. And when we get divorced... I gotta keep those clothes.” [35:32])

4. Alimony Tony’s Song Parodies & YouTube Fame

• Tony is also a “song parodist” (aka “Weirdamony Alimony Tony” on YouTube):

  “I, I do like, you know, the rewriting of songs that exist already, but using comical lyrics in place...” [40:11]

• Performs:
  • Justin Timberlake’s “SexyBack” Parody: “I'm sending dinner back. I didn't like these rolls...” [43:51]
  • Attempts a medley; admits his “tumors”-themed Fleetwood Mac Rumours parodies were “very grim.” [45:32]
  • Inability to remember lyrics sparks a new bit where the group tries to guess what songs mean instead ("Tony’s YouTube channel should be: you tell him a song, he tries to remember what it's about." – Jason Mantzoukas [51:45])
• Highlights include attempts at:
  • Britney Spears’ “...Baby One More Time”
  • Smash Mouth’s “All Star”
  • Alanis Morissette’s “Ironic” and “You Oughta Know”
    All devolving into elaborate, tortured exegeses by Tony.

5. Wealth, Tunnels, & The Surreal Logic of Riches

• Tony reveals his independent wealth derives from his family’s invention of gaseous paper, used by NASA (paper that “disintegrates upon touch” [64:41]).
• Discusses his billionaire bug-out plan:

  “...network of tunnels under the earth for rich people. ...Been a place for hundreds of years, and it’s a place where the world’s wealthiest people are all going to meet up.” [73:21]

• Provides a “Hotel California”/Eagles-style song parody revealing a secret access point:

  “On a daylit suburban freeway, the world is about to end. I went underground with several of my trillionaire friends...” [74:55]

6. Big Sue’s Soaking Wet Carpet Emporium

• Enter Big Sue (Lapkus):

  “I'm in a new relationship, but I'm worried that... he might not be who he says he is.” [85:47]

• Business woes:
  • Store flooded by toilets she refuses to fix (“I keep shitting.” [87:52])
  • Carpets for sale are “sopping wet,” “weigh 10 times more than you want them to.” [90:41]
  • Invention: makes a “squatty potty” out of stacked carpets, but is disappointed to learn the real product exists [90:04]
• Sue inhabits a “tiny home” between two alleys, achieved by magic shrinking powers [94:28–94:53].
• Revelations: she has sent her online boyfriend (“a literal catfish,” then revealed to be a model) “a hundred million grand” worth of chocolate bars (and is now bankrupt) [102:48–102:55].

7. The Chief’s Carmen Sandiego Obsession

• [115:19+] The Chief enters, full “from the beautiful island of Chicago,” to hunt alleged criminal Carmen Sandiego.
• Chief describes Carmen’s global monument thefts, from the St. Louis Gateway Arch to the Eiffel Tower in Las Vegas to Chicago’s famed iO theaters:

  “For a long time, my team was just teenagers answering questions about geography.” – Chief [118:26]
  “All of my money is crowdfunded. ...I am not a federal agency. In fact, I shouldn’t be doing the work that I’m doing. It’s quite illegal.” – Chief [120:44]

• The Chief is goaded about her years of failure, accusations of being “attracted” to Carmen, and her own cowboy cop tactics.

8. Incredible Live Improv Scenes

The cast explodes into a series of off-the-wall roleplay sketches and “scene work,” escalating in absurdity:

Rug Store Skits

• Scott, Tony, Sue, and others act out rival carpet shops, featuring everything from “the Dink Dink Man” (a local legend who steals children’s feet) to squatty potty innovations.
  • "There's a spirit called the Dig Dick Man. ...He steals children from their beds, and he tickles their feet with a feather." – Alimony Tony [93:17]
• “Classic Dink Dink Man, always tickling those kids.” – Jason Mantzoukas [98:58]

Airport Catfish Drama

• Sue attempts to confront her “catfish” boyfriend at the airport, only to be stymied by thick glass, noise, and confusion – executed as farce, with callbacks to the Dink Dink Man (“Let's plug these chargers into the Dink Dink Man and bring him back to life!” [110:38]).

Snake Store Madness

• A snake emporium sketch, with Lapkus as the “mascot snake,” interspersed with the Chief’s quest for clues from snakes (“I have a question...I'm looking for someone as slithery as you. Her name is Carmen Sandiego. ...Supple breast the size of winter cantaloupes.” – Chief [124:03]).

Notable Quotes

• Alimony Tony on Marriages:
  “I'm honest about two things: I cannot make a child, and I love to pay alimony.” – Alimony Tony [34:14]
• Jason as the Audience’s Deathbed Companion:
  “Many of the people that are here tonight, I expect to be by my bedside in my last moments.” – Jason Mantzoukas [15:53]
• Alimony Tony on Wealth:
  “My mother invented gaseous paper... it was used in the NASA space program. ...You have three states of paper: solid, liquid and gaseous.” – Alimony Tony [64:41]
• Big Sue on Carpet Sales:
  “We're having a liquidation sale right now. ...Please, God, take the rugs. They're shag, they're wet, they're soggy. They weigh 10 times more than you want them to.” – Big Sue [90:41]
• Chief on Carmen Sandiego:
  “She’s a criminal. I am there to catch her. Grab her by the waist. Hold her tight. ...Do a cavity search. If I may.” – Chief [117:07]
• Alimony Tony’s Song Parody Style:
  “I like the rewriting of songs that exist already, but using comical lyrics in place of the lyrics that are already there. ...Uploaded to YouTube under the screen name Weirdamony Alimony Tony.” – Alimony Tony [40:18]
• On Tunnel Networks for the Ultra-Rich:
  “The network of tunnels under the earth for rich people. ...Where the world’s wealthiest people are all going to meet up.” – Alimony Tony [73:21]
• Chief on Law Enforcement:
  “All my money is crowdfunded. ...In fact, I shouldn’t be doing the work that I’m doing. It’s quite illegal.” – Chief [120:44]

Key Timestamps for Segments

• Opening Chicago banter / death stories: [04:15–17:50]
• Alimony Tony’s introduction & life philosophy: [25:23–39:48]
• Song parody bits (Timberlake, Britney, Fleetwood Mac, etc.): [40:11–49:01]
• Millionaire tunnels & billionaire hideouts: [73:01–76:27]
• Big Sue’s wet carpet business / liquid assets: [85:08–90:41]
• Sue’s catfish boyfriend, online love woes: [98:10–104:09]
• Snake store improv scene: [123:13–134:00]
• Chief’s perpetual chase of Carmen Sandiego: [115:19–121:14]

Running Gags & Recurring Bits

• The Dink Dink Man:
  A Chicago urban legend who “steals children from their beds and tickles their feet with a feather,” popping up in countless sketches, adding a surreal local flavor.
• Wet carpets & toilet humor:
  Sue’s endlessly wet, unsellable rugs, and the grimy life of her business.
• Absurd success of Tony’s YouTube parodies:
  Each video with a view count of “one... usually me checking to see if it uploaded okay.” [40:55]
• Big Sue’s online catfish saga:
  She’s scammed by a model pretending to be a literal catfish, blowing through “a hundred million grand.”
• Chief’s law enforcement futility:
  Inability to catch Carmen Sandiego, and her ambiguous feelings about her quarry.

Episode Tone & Dynamic

The episode typifies Comedy Bang Bang’s surreal, free-associative style and trademark blend of deadpan, wordplay, and off-the-cuff inspiration. Everyone is game to “yes, and” each others’ weirdest ideas; character attributes mutate scene to scene, stories spiral into left-field improvisation, and all threads are woven into a feverish collage of Chicago-specific references, recurring motifs (alimony, wet carpets, urban legends), and persistent meta-jokes.

Takeaway for New Listeners

If you’ve never heard Comedy Bang Bang before, this episode is an exemplar of its most anarchic, collaborative improv: rapid-fire character work, absurd backstories, live audience energy, and fearless exploration of the absurd.

You’ll come away acquainted with:

• Alimony Tony’s perverse joy in divorce,
• Big Sue’s heroic capacity for embracing failure,
• Chief’s maddening codependency with Carmen Sandiego,
• And the group’s infinite capacity to extract comedy from the silliest premises.

Endnote

This Chicago tour stop stands out as a free-flowing, joke-studded celebration of CBB’s open-door, anything-can-happen ethos, with the cast and audience in joyous sync.