The Dollop is easily my top choice for that. 1908 New York to Paris Car Race is one of the funniest things I’ve ever listened to in my entire life.

Trashfuture - It’s Chapo but plus reviews of incredibly stupid or evil startups.

Worst of All Possible Worlds - Case studies in the pop culture of a dying empire. Some real laugh out loud episodes are 38 - The Gang Exploits a Teenager’s Death (Dear Evan Hansen), 62 - Minions, and 74 - The Boss Baby. They also review episodes of Adventures in Odyssey, a long running evangelical children’s radio play, and those episodes are always great.

Your Kickstarter Sucks.

Well There’s Your Problem - while the nominal topic is engineering disaster, it’s generally irreverent in a black humor kind of way and has a sarcastic sense of humor about most of the people involved in each disaster, especially when the reason for the disaster is political bullshit

You’ve probably tried these, but just in case:

• Comedy Bang Bang: 'Humanity(and the Animal Kingdom)'s Podcast." “The show where they talk to Interesting People.” A cantankerous host chats with guests (celebrities and improv comedians playing characters) in the style of a late-night talk show. This is my favorite show; it makes me laugh out loud every week, and there are occasional episodes during which I have to stop the podcast because I’m crying laughing. The ten-hour 10th Anniversary Special was one of these. Another was in an episode a couple years ago - there was a moment when a comedic actor was asked to produce the sound he makes when performing cunnilingus that obviously I still think about because it was so fucking funny. I was doubled over, breathlessly cry-laughing in my kitchen over that one, jfc.

• This Is Important: The Workaholics guys hang out and chat. It is always raunchy and hilarious. They’re on tour right now, and the live episodes are great.

• Stop Podcasting Yourself: Two Canadian comedians and a guest have a chat. This is less balls to the wall silly but still pretty entertaining. They do an “Overheards” segment where they talk about weird/funny stuff they’ve overheard in public and discuss audience submissions of the same, and it’s a rare week when at least one of those doesn’t crack me up.

• Threedom: Three comedians who are generally doing characters or heightened versions of themselves are instead just being their regular selves, hanging out and chatting, and the vibe is great. They are on hiatus between seasons right now, and some of their episodes are behind a paywall, but the show is a hoot.

• ActionBoyz: Three improv comedians discuss a different vintage action movie each week, for longer than the run-time of the movie. This is mostly behind a paywall, but there is a free feed with enough episodes to let you figure out whether you like it. I don’t particularly care about action movies and haven’t seen most of the movies they talk about, but I love this show. They do pretty spot-on impressions of Arnold, Stallone, Van Damme, Trump, and many more, and they get off on some pretty wild tangents, often in those voices.

• Baby Geniuses: Two best friends - a comedian/comedy writer and a comic artist - chat about their lives and the world and have a couple silly segments. Their “Wiki of the Week” segment is delightful, and the topic of the week gives the episode its name. Aug 7’s episode “Jizz (birding)” was particularly memorable.

I can suggest memorable episodes of the other shows too, if that would be helpful. I also have a friend behind some paywalls who could maybe help with any of those shows that interest you.

Hopefully at least one of these is new and enjoyable to you!

I’ve heard of My Dad Wrote A Porno but haven’t tried it yet - any particular episodes you’d recommend?

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Tom walker and Demi lardner just have a great time talking to each other I don’t know what to describe it as but i truly get the most laughs per episode out of BST

Trillbilly Workers Party is pretty good

Not Another DnD Podcast

https://naddpod.com/

Has me constantly crying laughing.

The only podcast that consistently makes me laugh out loud is the Hamish and Andy podcast. At least one good chuckle a week.

I really feel like I have to pre-emptively defend myself on this one, the duo is a household name in Australia and it’s about as middle of the road as podcasts go, but, I can’t help but love it.

Other shows are super hit and miss, like, I like Boonta Vista but it’s more of a ‘I’m smirking because this is kinda funny’ and has its moments but they’re fewer and far between recently. I’d still give it a listen to see if it scratches that itch for you.

The Danger Club is a Pathfinder podcast that frequently has me in stitches as they “yes and” each other into increasingly ridiculous claims and scenarios. If you have any interest at all in TTRPGs it’s worth a listen.