Oops All Segments

Oops All Segments

Hosts Thomas and Kevin navigate their way through absurd challenges, silly trivia, and curious conundrums while letting the segment wheel (and the audience) decide what comes next.

Episodes

June 16, 2025 31 secs

Our most urgent episode yet.


00:00 Intro & Check Ins


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


Born (with the cast of Suddenly, Last Summer) - Oops All Segments - 137


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Jesse swings in to talk about the Switch 2 release, feeling like a king among nerds, and what variations on Tennessee Williams’s classic would be better. It’s a wild ride.


00:00 Intro & Check Ins

21:00 Merry Bergen

29:16 A Vehicle Named Emotion


Islamic Relief Canada Gaza Emergency Appeal:

https://www.islamicreliefcanada.org/emergencies/palestine-appeal


A Streetcar Named Desire by Tennessee Williams (June 11 - 15 in Winnip...

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June 2, 2025 55 mins

Friend and actor Tasha Roth drops into the pod to chat her new-found affinity for Winnipeg Pro Wrestling and finally answer Kevin’s old text messages. The crew dives into their artwork of their youth before Tasha takes them on a journey of self-care.


00:00 Intro & Check Ins

18:07 Artist Corner

36:39 Self-Care Sunday


A Streetcar Named Desire by Tennessee Williams (June 11 - 15 in Winnipeg):

https://www.the28thminute.com/a-str...

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GTA expert and regular guy Ian Ingram joins the guys to chat musicals before diving into Barbie’s Dreamhouse. After doing their best to design the home of their deepest desires, Ian leads the duo in an anime contest. It’s a real nail biter.


00:00 Intro & Check Ins

12:13 Barbie’s Dreamhouse

20:56 Lost in Translation


Ian Ingram:

JHG Creative:

https://www.instagram.com/jhgcreative/


A Streetcar Named Desire by Tennessee Willia...

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Comedian and voice actor Freddie Powers starts by dream casting our Oops All Segments post-show host before diving into their experiences at summer camp.

Then they chat pet peeves and problems (specifically Freddie’s frustrations with Hot Pot).

Freddie takes the trio to toy town for some puppet play. 

Then the trio wish Thomas’ mother Melissa Steele a happy birthday on air.


00:00 Intro & Check Ins

13:59 Worst Pet You Ever Had

26:...

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May 12, 2025 53 mins

Funny friend Andrew Kerr aka xXxbluntk1ll4xXx locks in and lets loose with Kevin and Thomas. The trio chat about things serious and silly before digging into Thomas’ finances.

Andrew takes over with a super segment regarding few of his favorite uncles.


00:00 Intro & Check Ins

15:12 Chump Change

23:47 (A)ndrew's (S)uper (S)egment


Andrew Kerr:

www.cigarettes.com


Secret Family at the Annoyance Theatre (Thursdays at 8pm in...

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Thomas dishes about his latest trip across the pond while Kevin loses some locks. Then the boys take a horrifying look at the past before playing Wordle.


00:00 Intro & Check Ins

13:56 Internet History

42:43 Wordle


Trigger Happy: https://www.theannoyance.com/show/trigger-happy%3A-annoyance-signature-improv


Secret Family at the Annoyance Theatre:

https://www.theannoyance.com/show/secret-family


A Streetcar Named Desire in Win...

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Funny friend Jillian Mueller swings through. After Thomas and Kevin try to get Jillian to feature them in the Chicago Reader, they do a Conclave Oops All Segments-style (spin the wheel). Thomas poses to Kevin and Jillian his deeply troubling Cupcake Quandary. 

Things get repetitive for a while before Jillian gets the boys into sharing beverages with cryptids! 


00:00 Intro & Check Ins

12:06 The Cupcake Quandry

22:21 Repeater

25:3...

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Friend and Secret Family member Haley Gillman gets familiar with the guys as they live react to one of Thomas’ strongest pieces of creative work. Then they get into each other’s Letterboxd accounts and things get critical.


00:00 Intro & Check Ins

14:23 Let’s Check in with a Text Thomas Got From Kim

21:55 That’s What She Said

35:22 Letterboxd Moment


Haley Gillman:

Secret Family: https://www.theannoyance.com/shows

Fan Fiction: h...

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April 14, 2025 53 mins

A blast from Thomas and Kevin’s past brings the friction as Miguel Gauthier joins the duo. Miguel cracks out his famous jokes as the boys get gross and go over their writings from the past. 

Miguel introduces Kevin and Thomas to See Ya Ladle and they get their food gripes on. 

Finally, the trio flash back to fashion faux pas from their past.


00:00 Intro & Check Ins

14:26 Throwback Attack

30:48 See Ya Ladle

42:20 Bad Fit


Miguel...

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Funny friend Lola Selby pops in to spit some truth about Pedro Pascal’s coffee order and get overstimulated. Kevin gloats about his viral success as a rapper and Thomas explains his not-so-modest proposal.

The trio chat about the best parts of their living quarters before Lola puts the boys into a devilish situation of ethical dilemmas.

Kevin then pisses off Lola so much they leave.


00:00 Intro & Check Ins

21:10 Coolest Space

27...

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March 31, 2025 58 mins

Actor and friend Ben Krawchuk scampers his way into our world. The trio tackle Kevin’s love of Grimace while Ben discusses his past as a Hamburger. Kevin then takes the white boys through the national anthem of Trinidad. After that, Ben gets the boys to punch up dramatic films. Then the boys take it to the playground and talk strategy.


00:00 Intro & Check Ins

13:26 National Anthem Throwdown

24:06 Punch-Ups

40:34 Four Square &am...

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March 24, 2025 49 mins

Comedian and improvisor Tyra Banda jumps into our zone for some job advice. After some pet talk, Tyra chooses a musical champion to represent them, Thomas hides behind James Baldwin, and Kevin delivers some bad news.

Tyra then gets Kevin & Thomas to help assemble a rubric. 

Thomas calls his mommy.


00:00 Intro & Check Ins

11:32 Birthday Battle

24:14 I’m a University Improv Professor: What Does That Mean?

37:59 I Need an Adult

  

Tyr...

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March 17, 2025 52 mins

Comedian and friend Brian Park gets hacked and ends up on the show. The guys talk Canadian vs. American politics, Severance, and Secret Family Sketch. Then the trio dive into the most exciting way to die. Then Brian takes action as Thomas and Kevin go head to head and face off in Face Off: The Segment.


00:00 Intro & Check Ins

20:40 Die Another Way

31:40 Face Off: The Segment

  

Brian Park:

https://www.instagram.com/secretfamilysketch

...

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Comedian Carmen Christopher (The Bear, I Think You Should Leave) joins us for a wild time. They chat Trump (obviously). Then Carmen takes on a devilish role as he assigns Thomas and Kevin hellish punishments before receiving one of his own. Carmen confesses some IO crime before Punished Thomas and Kevin dive into their ice cream nostalgia. 


00:00 Intro & Check Ins

10:29 Hell on Earth

30:36 Hometown Ice Cream

 

Carmen Christopher...

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The freshly clipped wings of the Hill Kings find the duo of Brad Hild & Chris Covey in the nest of Kevin & Thomas at Oops All Segments. After Brad dishes on his vasectomy, the quadrant go trio as Thomas (soon Travis) signs off.

Then the trio dive into the life of Jim Varney before playing My Movie.

Then the Hill Kings take over control as Chris walks us through a draft of hot male cartoon characters and everyone balls out wit...

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February 24, 2025 55 mins

Comedian, improvisor and friend Dewey Parker hacks his way into the pod. The trio chat cereal before Dewey takes them through a hellish mallard-esque warm up. Then they get serious and sincere, discussing some positive developments in their lives.

Technical issues aside, Dewey makes the boys fight through a cue-ball-esque quiz.


00:00 Intro & Check Ins

17:48 Satan’s Duck

23:00 You Have the Keys Within Yourself to Transform Your ...

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Friend and improvisor Kerri Woloszyn drops by to tease us with the prospect of Oops All Segments Trivia. Valentine’s day and partner birthdays are brought up. Then the trio tackles riddles as The Puzzler takes over.

Kerri takes Thomas and Kevin into the Golden Survivor contest (a reality show title game). Hatred and happiness fly as the trio trip their way to the finish line.


00:00 Intro & Check Ins

18:20 The Puzzler

27:50 The ...

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February 10, 2025 48 mins

Friend, writer, and comedian David Resnick blasts in while they chat the origin of ‘fap’. Then they get into the retirement of the Blue Man Group.

Then they flip a monkey in to Eternal Sunshine, Stroker Ace, and There Will Be Blood.

Casting their vision into the future, the boys then predict how they’d fair in a post-apocalyptic scenario.

Finally, they indulge in a review of the Vanity Fair headlines and chat Grammy.


00:00 Intro & ...

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February 3, 2025 53 mins

Improvisor & designer Neftali Morales steps into the dojo with Kevin and Thomas. After a bit of banter, the trio tackle an online hip-hop quiz where Thomas is mostly just around. Then Neftali takes them through a classic improv game of Zelda Roleplay. Finally they discuss impactful films on them, such as Batman Returns, the Adam West ‘60s Batman film, and It’s a Wonderful Life.


00:00 Intro & Check Ins

15:38 Rap Pop Qui...

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