Unsubscribe Podcast Ep. 251 Summary

Episode Title: Comedian Ryan Long Tells The Best Joke Ever
Release Date: February 16, 2026
Host(s): Eli Doubletap, Brandon Herrera, Donut Operator, The Fat Electrician
Guest: Ryan Long

Episode Overview

This lively episode features comedian Ryan Long joining the Unsubscribe crew for an unfiltered, far-ranging conversation about the comedy grind, internet fame, the evolution of stand-up, and the wildest moments from both their careers and live shows. They dive into how the internet and social media have changed entertainment, how regional culture shapes comedy, bombing on stage, and the realities of live touring—plus, Ryan finally shares a joke they dub "the best ever." The banter is packed with dark humor, roasts, self-aware industry insights, and behind-the-scenes stories for comedy and podcast fans alike.

Key Discussion Points and Insights

1. The Weird World of Internet Fame

• Internet content creators now rival or surpass traditional celebrities but often exist in their own digital bubbles.

  • Ryan on the phenomenon:

    "You look at the podcast charts... Rogan, some guy named Dave... Who’s this guy? 8 million views on every video. And you’re just like, what’s going on over here?" (02:11)

• Discussion of viral, niche influencers:

  • Hoof Guy who cleans horse hooves for millions of views, Plumber influencer, and Subway sandwich guy who became trapped by the content that made him rich.

    "He’s the first guy that if he loses his job at Subway, he loses half a million dollars." (04:49)

• Creators can get boxed into their "thing" (cleaning, mowing, making sandwiches) and become more famous than legacy media figures, prompting laughs and complaints among the hosts about "the law of diminishing returns." (04:01)

2. Ryan's Comedy and Creative Journey

• Ryan recaps his roots:

  • Toronto band scene, early video/“cable access” shows, and transition into stand-up.
  • Was originally in a ska/punk/rap band and pivoted to comedy after Tom Green-style street skits.

    "We did all these DVDs... It was like, filming crazy little videos... then made a pilot and sold it..." (19:16, 21:36)

• Stand-up consumed his life after the first try:

  "I’ve done standup almost every night for the last 15 years now." (22:36)

  • The process required “five to seven years” before stand-up felt natural.

    "It's super hard to not be that good at [stand-up]... It’s the hardest for the first five years." (26:33)

  • Anxiety comes from unknowns, not crowd size:

    “If I was doing a show for seven people and someone I care about walks in—that’s when your brain starts going weird.” (23:08)

3. City Vibes and Scenes: New York, LA, Austin, and Beyond

• Comedy, like other arts, is shifting away from needing to be in New York or LA. Austin is emerging, and low rent cities foster creative “incubators.” (10:46)
• Locational differences affect comedic style and audience relatability:

  "New York comics... slightly grittier and funny, LA... just, like, gay. Guess which city's which." (12:16, jokingly)

• Regional edge:
  • In NY/LA, some topics are less edgy; in Texas, "talking shit about God" is edgier than in NY, where it's mundane.

  "In New York, that’d be the least edgy thing you could ever do." (65:02)

4. The Grind, Bombing, and Perfecting Material

• Mastery in stand-up comes only with brutal, repeated failure:

  "When you’re just there and you’re eating it and there’s nothing you can do—and you’re three years in, don’t even have the tools—this is the worst thing…” (29:36)

• Worst bombing story:

  “I followed a guy in a wheelchair, hand with cerebral palsy... talking about fingering girls... Black guys falling out of their chairs laughing. Then I go up, make a gay joke—everyone's like, yo, AYO! Nine more minutes, then a DJ starts the ‘get off stage music.’” (30:43)

• Stand-up is “public speaking where you’re expected to make people laugh”—the scariest for most people, harder than jumping out of planes. (29:07)

• Dangers of reusing material, and the broader expectations of internet audiences:

  “If you have an hour and someone’s a big fan, they’ll come a second time, but not a third if it’s mostly the same set...” (128:48)

5. Internet vs. Traditional Entertainment & Touring Realities

• TV unions and film industry rules—contrasted with internet freedom:

  “They're making themselves obsolete... They said if you want to make Instagram videos on your own channel, you can't because you're a union actor, so you have to pay the fee.” (43:24)

  • Barriers to entry are lower; creators can "skip the middlemen."

• Live show culture clashes (especially in union houses or specific regions like Jersey):

  • Venues, unions, and staff can sabotage shows; sometimes the worst part is the employees, not the fans.

  “Jersey... the fans loved it. It was the employees. Patted us down for the green room... just assholes the entire time.” (34:10)

• On opening acts and the importance of warming up an audience:

  "That's a no-brainer... Have someone do something beforehand.” (138:45)

6. The "Best Joke Ever"

• The hosts press Ryan to tell what they bill as “the best joke ever.”

  “Ryan Long says this is the best joke ever written. He wrote it, personally, the funniest joke—ever written.” (56:05)

• Ryan delivers a rapid-fire bit about British colonization, complete with jokes about Jews, Jamaica, and England's legacy:

  “England went to the Middle East and gave them the best present you could ever ask for: 85,000 Jews...” (58:26)

  • (See detailed quote in Notable Quotes)
• Immediate reactions:

  "That is the viral clip that just happened, so let you know. That is the viral clip right there." (59:06)

7. Where Comedy Kills (and Where it Doesn't)

• Regional relatability is paramount:

  "Sometimes, the pushback the joke’s built on—no longer exists. Then you’re like, ‘so, what are we doing here?’" (63:54)

  • E.g., Indian jokes in Toronto, blank stares in other cities.

• Adjusting edginess by region:

  "There’s a difference between offending people, and offending people in a funny way." (65:52)

• The importance of "writing for the room"—whether that means the “city/urban” crowd or the “Texas serious guy,” and knowing when the edge flips. (64:18)

8. Social Media, Algorithms, and the Creator Life

• The algorithm pushes content you might have only mildly sampled; your feed can become bizarre overnight.

  "You ever get into another algorithm? Like Black Twitter or Muslim algorithm... And you realize, I don’t know any of this shit.” (68:55)

• Hosts comment on the “permanent effect” of what you watch, even by accident.

  • "Sometimes I fall asleep while doomscrolling... the algorithm thinks my watch time is 100% on that." (69:51)
  • “Ever reset it? Takes balls.” (70:15)

9. Life, Jobs, and the Pursuit of Comedy

• Ryan describes patching together a living via “rackets”—video work, band income, early comedy.
• Advice to young creatives:

  “Find out how to make 30 grand a year with the least amount of hours possible... and then never nickel-and-dime time in your pursuit.” (123:10)

• The “career” of comedy is a lifestyle, not just a job:

  “This isn’t a thing you do. This is a life you have.” (119:37)

10. Military & Brotherhood, Crime, and Growing Up Canadian

• Comparing the camaraderie of the army with band/comedy life and why military brotherhood is unique.

  “I would put my life in front of my own for my... That’s very hard to have anywhere else.” (104:19)

• Wild stories from Toronto:
  • School shootings, carjackings, crime in “portables” (portable classrooms)—and a Toronto street/gangster accent.

  "[Toronto accent:] 'Yo, honestly, dog. Yo, for real, yo. Mens is actually crazy, yo.'” (109:17)

Notable Quotes and Memorable Moments

Opening on Internet Fame

“You look at the podcast charts… Rogan, some guy named Dave… Who’s this guy? 8 million views on every video. And you’re just like, what’s going on over here?” — Ryan (02:11)

On Getting Boxed In By Viral Fame

"Subway guy... now he's rich but if that's his business... if he loses his job at Subway, he loses half a million dollars." — Host (04:46)

On the Stand-Up Grind

"I’ve done standup almost every night for the last 15 years now." — Ryan (22:36)

“I’ve followed a guy in a wheelchair... Black guys falling out of their chairs laughing. Then I go up, make a gay joke—everyone's like, yo, AYO!... Then DJ starts 'get off stage' music... walked off and into an ocean.” — Ryan (30:43-31:43)

On Bombing vs. Killing

"You do learn more from your bomb, but... there’s depreciating returns. You wouldn’t be just like, well I’ve been bombing for 10 weeks straight… I’ve REALLY been learning." — Ryan (78:44)

On Regional Comedy

“Sometimes, the pushback the joke’s built on—no longer exists. Then you’re like, ‘so what are we doing here?’” — Ryan (63:54)

The "Best Joke Ever" (Ryan's Colonization Bit) — [~57:31-59:01]

"Do you guys know about colonization?... England went to the Middle East and gave them the best present you could ever ask for, which is 85,000 Jews. And that’s so much to thank you by the way, I wish I had 85,000 Jews. Jamaica was jealous, they’re like, we want Jews. They’re like, you already have. Black people don’t get greedy. And they said, once they become reggae stars, we’re still gonna need a few Jews to manage them. And they said, the Jews can’t help because they’re busy sending over the black people. Now that is 20% historically accurate."
— Ryan (57:31–59:01)

On Life as a Comic

"This isn’t a thing you do. This is a life you have.” — Ryan (119:37)

On Building a Career

"Find out how to make 30 grand a year with the least amount of hours possible... so you can spend your time doing other things and never nickel-and-dime time in your pursuit.” — Ryan (123:10)

Timestamps for Key Segments

• 02:00 – Internet microcelebrity/viral fame & content pigeonholing
• 06:30 – Ryan’s entry into comedy/band background
• 09:47 – How the comedy scene works in NY vs LA vs Austin
• 23:08 – Stand-up anxiety and what actually makes a comic nervous
• 29:36 – Public speaking, bombing: hardest moments and learning curves
• 30:43 – The infamous “worst bomb” story
• 56:05 – "The Best Joke Ever" build-up
• 57:31–59:01 – Ryan’s colonization bit (the "best joke")
• 62:41 – Regional comedy: differences in jokes that "kill" city vs rural
• 65:52 – Navigating offense vs. humor
• 78:44 – Learning from failure vs. success
• 119:37 – Comedy as a life, not a hobby
• 123:10 – How to piece together a creative career
• 142:01 – Ryan’s current tour plans

Additional Moments and Humor

• Podcast Roasts:
  • Hosts relentlessly tease each other about ethnic ambiguity, music tastes, "fish guy" nicknames, and accidental racism right from the start.
• Dark Jokes:
  • The group regularly trades in deadpan, bro-style anti-PC humor and war stories, with frequent self-aware comments ("editor, when you clip that as a short, please leave my face out of it," 59:11).
• On Audience Management:
  • "Jersey employees... just assholes the entire time, and we didn’t know what we did." (34:07)
• On Social Media Algorithms:
  • “Ever reset your algorithm? It takes balls.” — Ryan (70:15)

Where to Find Ryan Long

• Socials: @RyanLongComedy
• Podcast: The Boys Cast with Ryan Long
• Tour Dates: RyanLongComedy.com

Episode Tone and Style

• Irreverent, fast-paced, and full of inside jokes and roasts
• Dark, meta humor with lots of winking self-awareness and industry commentary
• Blends behind-the-scenes anecdotes, practical advice for creatives, and rapid-fire crowd banter.

For Listeners New to Unsubscribe

Expect wild tangents, belly-laugh storytelling, and a brutally honest look at modern comedy from both sides of the stage—and don't be surprised if audiences, staff, and even the hosts themselves come in for a roast.

End of Summary