Friend, improvisor and artist Obediah Freeman joins the fray and checks in with Kevin and Thomas to make sure they’re safe. After navigating the social etiquette of talking during haircuts and massages, the trio dive into a game of Mob Mentality. After amassing a following of people wronged by airlines.

Obediah helps the boys destroy loneliness as they tackle the improv game Speed Dating.

0:00 Intro and Check In

20:45 Mob Mentality

30:36 Speed Dating

40:55 Hungry Hungry Hypocrites 

Obediah Freeman:

Unexpected Productions:

https://www.unexpectedproductions.org/

www.instagram.com/instadiah

Kevin Ramberran:

Love is Blank (Feb. 14 in Winnipeg @ 7pm):

https://3common.com/event/love-is-blank-improvised-instant-soulmates/697a2eb237a1f326de8ecb0e

Yours Truly (Feb. 14 in Winnipeg @ 9pm):

https://3common.com/event/697a30c837a1f326de8ece7a

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

Soda Pop! Pop Up Show @ The Saint (Winnipeg): https://3common.com/event/soda-pop-a-pop-up-improv-show/696969afc5471f8284c9fb14

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

Epic Emotional Music by AShamaluevMusic

https://www.youtube.com/watch?v=hqCwWaebljg

FOLLOW Oops All Segments on Instagram: www.instagram.com/oopsallsegments

FOLLOW Oops All Segments on TikTok: www.tiktok.com/@oopsallsegments

SUBSCRIBE to Oops All Segments on YouTube: www.youtube.com/@oopsallsegments

Thomas and Kevin finally make good on a promise and get Davide Montebruno into the fray. The improvisor, voice actor, and funny fellow helps the boys navigate The Opposite Day Clause as they learn what the Opposite of Santa is. Kevin complains about Hidalgo and Thomas is reeling.

They reminisce about Marble Slab Creamery and their work life.

Thomas resists becoming Droz as Davide brings them into the Advertising Game. The trio sling Segments before diving into the lamentations of making their nut.

0:00 Intro and Check In

19:22 Worst Jobs

31:44 The Advertisement Game

40:55 Hungry Hungry Hypocrites 

Davide Montebruno:

Soap Scum presents Space Quest! (Feb. 10th in Winnipeg):

https://www.eventbrite.ca/e/soap-scum-presents-space-quest-tickets-1982077014707

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

Soda Pop! Pop Up Show @ The Saint (Winnipeg): https://3common.com/event/soda-pop-a-pop-up-improv-show/696969afc5471f8284c9fb14

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

Epic Emotional Music by AShamaluevMusic

https://www.youtube.com/watch?v=hqCwWaebljg

FOLLOW Oops All Segments on Instagram: www.instagram.com/oopsallsegments

FOLLOW Oops All Segments on TikTok: www.tiktok.com/@oopsallsegments

SUBSCRIBE to Oops All Segments on YouTube: www.youtube.com/@oopsallsegments

Actor and friend Cory Wojcik slips through the cracks and makes it into the show. The trio chat Thermea controversies, binoculars, and Elvis’ test scores. After unpacking their trauma, Thomas performs an ode to Norma Rae. Then Cory decides to use some grade-school tactics on the boys and put them through Emote. Then Cory helps set their sights on Davide Montebruno.

0:00 Intro and Check In

18:50 Recap Gleecap

26:05 The Go-Tos

48:38 Be Our Guest

Cory Wojcik:

The Last Wife: https://royalmtc.ca/Current-Plays/The-Last-Wife.aspx

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

Soda Pop! Pop Up Show @ The Saint (Winnipeg): https://3common.com/event/soda-pop-a-pop-up-improv-show/696969afc5471f8284c9fb14

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

Epic Emotional Music by AShamaluevMusic

https://www.youtube.com/watch?v=hqCwWaebljg

Monoculars (with Cory Wojcik) - Oops All Segments - 165

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Brad and Chris from the Hill Kings drag their tushies out of Arlen and visit us once again. Brad takes a break from baking bread and Chris steps out on his family to discuss our worst birthday memories before Brad forces us to predict how 2026 will go with his new segment, BRINGO.

0:00 Intro and Check In

13:25 It’s My Party & I’ll Cry if I Want To

35:28 BRINGO

The Hill Kings Podcast:

YouTube: https://www.youtube.com/@HillKingsPod/videos

Apple Podcasts: https://podcasts.apple.com/us/podcast/hill-kings-podcast/id1710916157

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

Soda Pop! Pop Up Show @ The Saint (Winnipeg): https://3common.com/event/soda-pop-a-pop-up-improv-show/696969afc5471f8284c9fb14

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

FOLLOW Oops All Segments on Instagram: www.instagram.com/oopsallsegments

FOLLOW Oops All Segments on TikTok: www.tiktok.com/@oopsallsegments

SUBSCRIBE to Oops All Segments on YouTube: www.youtube.com/@oopsallsegments

The Puzzle-Master Jesse Bergen unlocks the door to the studio and joins the show. After blaming their guest for their inconveniences, Kevin updates the crew on some insane traffic accidents that have happened near his restaurant in Winnipeg.

Jesse makes the boys get their Jay Leno on before the trio slide into Heardle territory once again.

0:00 Intro and Check In

15:50 Kevin’s Traffic Report

27:07 Headlines: Resurrections

48:28 Heardle

Jimmy Gatliff:

https://www.instagram.com/32doubleg

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

FOLLOW Oops All Segments on Instagram: www.instagram.com/oopsallsegments

FOLLOW Oops All Segments on TikTok: www.tiktok.com/@oopsallsegments

SUBSCRIBE to Oops All Segments on YouTube: www.youtube.com/@oopsallsegments

Funny friend Jimmy Gatliff controls themselves as best they can as the trio chat iconic films about women in space.

Jimmy then grills the boys on the gay-est things they’ve ever done.

Then the crew takes a crack at stand up on the spot and turns the podcast into an open mic!

0:00 Intro and Check In

13:21 Buoyant Girls

24:00 What is the Gayest Thing You’ve Ever Done?

37:25 Stand Up For Yourself

Jimmy Gatliff:

https://www.instagram.com/32doubleg

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

FOLLOW Oops All Segments on Instagram: www.instagram.com/oopsallsegments

FOLLOW Oops All Segments on TikTok: www.tiktok.com/@oopsallsegments

SUBSCRIBE to Oops All Segments on YouTube: www.youtube.com/@oopsallsegments

Funny friend Lauren Ainsworth flies in and figures out what kind of needles are allowed on planes. After debating the quality of Guy Ritchie’s Snatch, Kevin confuses Santa for Jesus Christ. The three then discuss the things that make them laugh the hardest.

Then Lauren tests whether Kevin or Thomas is smarter than a(n American) fifth grader.

Then Lauren helps the chaps find out the best way to make Thomas’ fiancé’s life easier as they venture to the frigid north that is Winnipeg.

0:00 Intro and Check In

10:55 What’s So Funny?

20:56 Are You Smarter than a Fifth Grader?

36:22 Kim’s Convenience

Lauren Ainsworth:

https://www.instagram.com/lamesworth_/

The Dude Cave at The Crescent Theatre (Alabama) Dec. 27th:

https://crescenttheater.com/tm-attraction/the-dude-cave-live-sketch-comedy/

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

How The Grinch Stole Improv! - Winnipeg - Dec. 27th, 2025:

https://3common.com/event/how-the-grinch-stole-improv-/6937361f0c7a8eeb21a69282

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

Fifth Grade (with Lauren Ainsworth) - Oops All Segments - 161

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Seattle’s Dominique Sagiao pops in as Kevin laments his new position as a groomer of men for Thomas. In this improv-chatter heavy episode, the trio reminisce about their favourite childhood games before diving Inside the Actor’s Non-Geographic Location and answering questions about their improv experience.

0:00 Intro and Check In

17:45 Childish Games

29:27 Inside the Actor’s Non-Geographic Location

Dominique Sagiao:

https://www.unexpectedproductions.org/

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

How The Grinch Stole Improv! - Winnipeg - Dec. 27th, 2025:

https://3common.com/event/how-the-grinch-stole-improv-/6937361f0c7a8eeb21a69282

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

Man with Balls (with Dominique Sagaio) - Oops All Segments - 160

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FOLLOW Oops All Segments on TikTok: www.tiktok.com/@oopsallsegments

SUBSCRIBE to Oops All Segments on YouTube: www.youtube.com/@oopsallsegments

It’s Good Vibes OR ELSE as Freya Parker appears as Thomas prepares for American Thanksgiving and Kevin celebrates Creme Brûlée. 

The Size Queen chimes in to help give a confused couple some advice on a sordid seasonal gift. 

After lamenting over presents not received, the trio tackle what might be a dog’s greatest Christmas before diving into the improv classic My Movie.

0:00 Intro and Check In

11:48 The Zaprudie Film

22:42 Wishbone Christmas

33:31 My Movie

Freya Parker:

https://www.improvnorth.com/shows

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

Club Soda Improv @ The Tara Theatre (Nov. 28, 2025):

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint (First Draft) @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

FOLLOW Oops All Segments on Instagram: www.instagram.com/oopsallsegments

FOLLOW Oops All Segments on TikTok: www.tiktok.com/@oopsallsegments

SUBSCRIBE to Oops All Segments on YouTube: www.youtube.com/@oopsallsegments

From the rainiest place on earth, The Mancunian Candidate Sarah-Lou shows us what’s what. The trio chat nips and tattoos before diving into the real estate markets in their area.

Sarah-Lou then vets Thomas and Kevin for the BAU as they play Psychological Profile Guess Who.

0:00 Intro and Check In

15:46 Move It, Move It

33:54 Psychological Profile Guess Who

Sarah-Louise Young:

Dick Whittington:

https://www.lighthousepoole.co.uk/event/dick-whittington/

Kevin Ramberran:

Club Soda Improv:

https://www.instagram.com/clubsodaimprov

Club Soda Improv @ The Tara Theatre (Nov. 28, 2025):

https://3common.com/event/6907861066d6aa3e6a489c67

Thomas Toles

Trigger Happy:

https://www.instagram.com/triggerhappycomedy/

Motorcycle Rocketship:

https://www.instagram.com/motorcyclerocketship/

Secret Family Sketch:

https://www.instagram.com/secretfamilysketch/

Blueprint @ IO Chicago:

https://ioimprov.com/shows/

Check out our DnD show: 'What We Do in the Basement’: https://podcasts.apple.com/ca/podcast/what-we-do-in-the-basement/id1552947049

Guess Who (with Sarah-Louise Young) - Oops All Segments - 158

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