Shoulda Said: A Standup Comedy and Improv Podcast

Joe Drew, Brooke Converse, Christopher McDonald, Forest Olsen, Jesse Shewfelt, Lisa, Sarah Edwards
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Shoulda Said takes a standup "joke jam", where a standup comic works out their joke ideas with fellow standups to try to make them even funnier, and combines it with scenes improvised based on ideas from those jokes. A group of amateur comedians from Toronto learn what they shoulda said instead when their sets have different angles shone on them when they make it up on the spot. Shoulda Said owes its existence to the concepts it stole from the podcasts Working It Out by Mike Birbiglia and Hey Riddle Riddle by Adal Rifai, Erin Keif and John Patrick Coan.

Episodes

  1. 12/31/2024

    Episode 5: Taking a Bullet

    2:27 – Forest thinks that breakup styles should be listed on dating apps, and then we visit an awkward set of breakups. 26:14 – Brooke tries out an idea for a sketch, then we visit a VERY questionable Tarot card reader. 36:23 – Chris learns that "I'll take a bullet for you" doesn't mean EVERY bullet, then a very talented chef finds a very exciting way to fire one of those bullets. 44:40 – Sarah tells us about how sensitive her nose is! Then, we explore ways that could go wrong. 54:57 – Lisa wonders why planes have all of those lights? And what other lights could planes have, anyways? (Recorded Nov 7, 2024)

    1h 6m

  2. 12/19/2024

    Episode 4: Boy Gross

    01:19 – Chris has done some investigation into a new app for busybody neighbours, then we see a scene with those neighbours. 18:25 – Forest thinks that people SHOULD talk behind their significant other's backs, then we visit a couple having an argument in a restaurant to see why it'd've been improved by a little secretive conversation. 42:57 – Brooke calls in from Spain with an idea for a sketch or a bit, which we take to its logical conclusion. 47:48 – Lisa has a new idea for doctors to make money! 54:03 – Joe has very...refined tastes when it comes to masturbation, and Forest wishes things were easier with the opposite sex. What if there was a way to combine the two? 1:15:27 – Chris discovers a new Duolingo setting! (Recorded October 10, 2024)

    1h 23m

  3. 10/16/2024

    Episode 3: Fair Enough

    Episode 3 is very different from the previous 2 episodes, and features in-depth discussion of bits, premises, therapy, trauma, and sex. This episode features Sarah Edwards, Forest Olsen, and your hosts Brooke Converse and Joe Drew. 03:31 - Forest goes "Forest Long" on a bit about a good friend of his who is a little *too* open about her interest in reading, and then we visit a made-up book club. 33:36 - Hear Forest's bit as it was performed live at https://www.instagram.com/softboyspresents/ 41:41 - Sarah has a novel use for her Apple Watch, and then we make up a whole lot of very realistic, not at all contrived uses for other pieces of everyday technology. 1:00:09 - Brooke has a premise that definitely doesn't lead us to think she's passive aggressive; nope, not at all. Then we invent a world in which everyone's second sentence is taken ENTIRELY RATIONALLY. 1:13:06 - Joe's most stressful time is related to his high-tech job. Then the group unpack his presentation style???

    1h 19m

  4. 09/11/2024

    Episode 2: Cheese-Eating Personality

    01:56 - Forest wonders whether scientists get weirded out by people who are on their side, and then somehow is hit on by German Greta Thunberg? 12:15 - Chris draws a parallel between self-help books and the Ikea Helper Cartoon, and then a couple nearly breaks up inside an Ikea. 24:01 - Other fights that Lisa and Chris have gotten into with their significant others. Entirely reasonable ones, of course. 28:58 - Sarah tries out her first bit, from a doggie daycare, and then is visited by dogs and cats from that doggie daycare. 41:06 - Lisa's freaked out by what's inside of her, which leads to a TWENTY MINUTE conversation about guts, Guts, what Sarah's "cheese-eating personality" means, Forest's ex, and being weirded out on the subway. 01:05:00 - Brooke has a premise about her mother in law, which leads to us discovering Forest's alternate personality, and start calling each other by the wrong names.

    1h 18m

  5. 09/02/2024

    Episode 1: You can't be atheist AND agnostic

    Welcome to Shoulda Said, a comedy podcast that mashes up a standup "joke jam" with improv scenes inspired by the bits being worked out. This episode's guest is Sandra Pascuzzi, a brilliant Canadian-Australian comic based in Toronto. 01:09 - An introduction to the format of Shoulda Said in the form of Jesse Shewfelt's confusing dating profile and religious views, and the impact that might have on potential mates 06:03 - Sandra Pascuzzi's views on Australian men, Lisa's relationship with an Australian bartender, and how that relates to a famous Australian author 15:30 - Lisa's misunderstanding around what to post on a social media app, Lisa's OTHER misunderstanding around what to post on a social media app, and an ex of questionable heritage 23:08 - The time Joe Drew was 100% sure he was going to die, other embarrassing ways you might die, and an increasingly unlikely 911 call 31:26 - Sandra wonders why men use lube, so naturally we learn quite a lot about Jesse, Forest, and Joe's penises. Plus, an improvised scene in a high school locker room! Be glad podcasts are an audio-only medium. 38:43 - Suggestions for Joe's "you're sure you going to die" bit, and an improvised party with a bunch of children envious over each other's costumes. 44:30 - Forest Olsen has a bit about when boyfriends forget they're not therapists, and we learn more about Jesse's dating life. Plus, aren't babies weird? This episode of Shoulda Said features Forest Olsen, Jesse Shewfelt, Lisa, and Sarah Edwards, and is hosted by Brooke Converse and Joe Drew.

    58 min
  • 5 Episodes

About

Shoulda Said takes a standup "joke jam", where a standup comic works out their joke ideas with fellow standups to try to make them even funnier, and combines it with scenes improvised based on ideas from those jokes. A group of amateur comedians from Toronto learn what they shoulda said instead when their sets have different angles shone on them when they make it up on the spot. Shoulda Said owes its existence to the concepts it stole from the podcasts Working It Out by Mike Birbiglia and Hey Riddle Riddle by Adal Rifai, Erin Keif and John Patrick Coan.

Information

  • Creator
    Joe Drew, Brooke Converse, Christopher McDonald, Forest Olsen, Jesse Shewfelt, Lisa, Sarah Edwards
  • Years Active
    2K
  • Episodes
    5
  • Rating
    Explicit
  • Copyright
    © Shoulda Said Podcast (2025)