Best Comedy Podcasts: Top 5 Funniest Podcasts

By podcast | May 10, 2023

Poddy people! Get your earbuds ready because I’m about about to run down the best comedy podcasts. You’re going to want these on your playlist. I’ll be covering everything from hilarious banter and insightful interviews, to a mixture of humor and heart. These podcasts are all served up by some of the best comics in the biz.

From number 5, I’ll work my way up to my all time favorite comedy podcast.

Ready? Let’s give it a go.

5. 2 Bears 1 Cave 

When you combine the comedic talents of Tom Segura and Bert Kreischer, you get 2 Bears 1 Cave, a podcast that showcases their hilarious and endearing bromance.

This dynamic duo banters, shares outrageous stories, and engages in playful competitions, all while making listeners feel like part of the conversation. 

The latest? They’re both on the testosterone train. Bert’s convinced he can feel the juice. But Tom? He’s always there to burst Bert’s bubble, especially when it comes to his wild ideas and his “fabulous shoulders”. 

 2 Bears 1 Cave delivers an irresistible blend of humor, nostalgia, and camaraderie.

4. TigerBelly 

Bobby Lee from MADtv? Yup, he’s rockin the mic on TigerBelly with his ex, Khalyla. That’s right, they’ve called it quits, but the podcast is still going strong.

And why wouldn’t it? They’re raking in the ad bucks. Quitting now would be like saying no to a mountain of cash.

Their chats are like a wild rollercoaster ride – pop culture, their own drama, the spicy and the scandalous, race – they put it all out there. No topic is off limits, which is the type of comedy I like.

They’ve got a really unique guest list, famous asians, comedian friends, and other people of influence.

And Bobby truly is one of a kind. His humor is a mix – part observation, part self-roast, with a dash of controversy. His Korean-American upbringing and his childhood trauma gives the podcast that extra kick.

Khalyla co-hosts and is the glue that keeps the show together. She’s smart, witty, asks the right questions and keeps Bobby in line.

3. The Tim Dillon Show

The Tim Dillon Show is a comedy podcast that covers a wide range of topics, often commenting on current events, pop culture, and politics. Tim isn’t afraid to question societal norms, governmental policies, and cancel culture.

Dillon often interviews exciting guests on his show, from other comedians and actors to  thinkers. These interviews are usually characterized by Dillon’s irreverent and often absurd comedic style, which blends satire, parody, and social commentary elements.

His solo episodes are my favorite. His ability to rant rivals Adam Carolla, and how he incorporates story into those rants is some of the best I’ve heard.

Also, this dude has his own way of seeing things, his brain’s always in overdrive. He questions the status quo and if you’re off base about something? Oh, he’ll let you know, but in a funny way.

His approach can be polarizing, but it has resonated with many listeners, who appreciate his candor, honesty, and willingness to discuss subjects many other shows might shy away from.

This is certainly one of the best comedy podcasts.

2. Bertcast 

Most of the time, Bert can be seen shirtless with his belly hanging out. He comes off as a giant doofus, but he’s a marketing genius, a great comic, and a hard worker. Oh, and a party animal, which he reps proudly. 

Apparently, the movie the National Lampoons movie, Van Wilder, is based off of Bert’s Florida State stories and reputation.

Bert tours A LOT; you can tell he leaves it all on the table for every show. Just look at how much his tour grossed in 2022. He’s one of the most successful comedians in the world.

Bertcast has helped propel his live act. He masterfully uses the podcast as a vehicle to sell tickets.

Bert’s known for his energetic storytelling and contagious laughter. He dives into conversations with comedians, actors, and other notable figures. However, he often interrupts them and interjects personal anecdotes into their stories. The narcism is hilarious.

He loves to clown on his wife and kids. But, you can tell he’s a solid dude, and it’s all in good fun.

Whether he’s recounting his crazy adventures or debating the merits of food and alcohol, Bertcast guarantees a fun and lighthearted listen.

1. This Past Weekend

Theo Von’s This Past Weekend perfectly blends hilarity and heart. Theo’s unique blend of storytelling, personal anecdotes, and off-the-wall humor makes him a special comedian.

Theo grew up in Louisiana, the impetuous for his style. You can definitely hear the twang in his cadence. He interviews comedians, musicians, athletes, actors, and other interesting characters. Listen, and you’ll understand what I mean by “characters.”

He’s had on a mortician, a cop, and Jimmy John – the sandwich guru, on the show this past year.

Theo shares some of his mental health struggles when he rocks the mic solo. In fact, he often takes calls from fans and advises them on issues they’re struggling with. I appreciate this. It brings a feeling of relatability to him and the show.

With Theo’s self-deprecating humor and genuine curiosity, you never know what to expect, which makes the which exciting. This really is the best comedy podcast in my book.

The Best Comedy Podcasts – Wrap Up

That’s a wrap on my comedic journey through the best comedy podcasts. These top 5 have made me laugh, gotten me through hard times, made me smile and given me enough memes to keep my friends and family busy for a long time to come.

But remember, in the ever-evolving universe of podcasts, there’s always room for more laughter. So, until my next tour of the best comedy podcasts, keep your earbuds in and your mind open.

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