Podcast Summary: "Straight Hoopin’ in Delray: Anthony DeVito Returns! – CHIT CHAT WEDNESDAY"

Podcast: The JTrain Podcast
Host: Jared Freid
Guest: Anthony DeVito
Release Date: November 26, 2025

Episode Overview

This week’s "Chit Chat Wednesday" brings a classic blend of comedic insight and industry talk as Jared Freid welcomes comedian and close friend Anthony DeVito back to the show. Broadcasting from Delray Beach, Florida, Jared and Anthony riff on Anthony’s new comedy special ("Straight Hoopin’"), self-promotion anxiety, the oddities of PR in comedy, building careers in stand-up, the idiosyncrasies of Canadian comedy culture, and the joys and awkwardness of comedy festivals. True to the podcast’s style, the conversation is peppered with personal anecdotes, humor, and cultural commentary—all maintaining the spontaneous and relatable JTrain tone.

Key Discussion Points & Insights

1. Promoting a Comedy Special: Anxiety, Awkwardness, and PR People

Timestamps: 02:32-07:50

• Jared enthusiastically announces Anthony's new YouTube special, “Straight Hoopin’,” and highlights the importance of audience support for independent projects.

  “You got to watch Straight Hooping…This isn’t you supporting Anthony. He’s supporting you. When there’s one set of feet in the sand, that was Anthony carrying you with laughter and love and joy…” – Jared (03:10)

• Anthony admits to feeling awkward about self-promotion and often resigning halfway through plugging his special.

  “I give up on the special…there are better things to do with 45 minutes of your life…” – Anthony (04:38)

• They riff on bizarre PR culture in comedy, with both comedians poking fun at the cold, intense persona of PR reps and their tendency to treat even small podcasts as A-list media.

  “It’s either gay man or Jewish woman…Like, chin out, watching, not laughing, not enjoying, just, like, making sure things go okay…” – Jared (06:07) “They’re so intense. They give you exactly what you think they’re gonna be…downright mean.” – Anthony (05:55)

2. Comedian Bios and The Art of Self-Description

Timestamps: 08:07-11:38

• The hosts discuss horrors of having bios read aloud at shows, how those bios quickly become embarrassing relics, and the aspirational, sometimes exaggerated self-myth-making comedians indulge in.

  “It’s as if they’ve reached down my throat and grab my anus to, like, reverse me inside out.” – Jared (08:31) “There’s always…kind of flowery language…about, like, you, like, what you thought you were supposed to write in a bar bio…” – Anthony (09:25)

• Jared notes the need for multiple bios for different occasions, and both reflect on presenting themselves as more accomplished in the early years than they truly were.

3. Comedy as a Career: US vs. Canada

Timestamps: 11:38-14:44

• Jared offers his theory that Canadian comedians are more comfortable and professional about their work, possibly because the culture regards comedy as a legitimate middle-class job.

  “As if Canadians were, like, with a briefcase, going to work…in Canada, it just felt more normalized that comedian could be a middle class job.” – Jared (12:18)

• Anthony points out the added professionalism and seriousness often required of Canadian comics who move to the US, having had to navigate immigration and higher barriers to entry.

4. Delray Beach, Odd Jobs, and Tajin Tangents

Timestamps: 14:28-18:10

• Jared describes how declaring himself a comedian in Delray elicits confusion, as the locals are more likely to expect paddleboard instructors and parrot owners than stand-ups.
• This segues into a funny exchange about culinary trends, specifically Tajin (the Mexican seasoning).

  “Do you like Tajin? …It’s such an abrasive taste.” – Anthony (15:20) “I think we…think we have to like it to seem like we get it…I have, like, white girls correcting me on how to say it…” – Jared (15:26)

• The hosts jokingly discuss "white guilt" and perform a playful mock-interrogation of Anthony’s lack of Tajin knowledge.

5. Building a Personal Brand vs Joining a “Team” in Standup

Timestamps: 18:10-22:55

• Jared analyzes how today’s comedy audiences gravitate toward comedians with clear "teams" or identities, often political or cultural. They lament that nuanced comedy is harder to market.

  “Nuance and context is really not what people are looking for, but people meaning the stupids.” – Jared (22:09)

• He uses debates over chicken “flats or drums” as a metaphor for how people crave sides and absolutes, not gray areas.

6. Comedians’ Dreams: Modesty Over Mania

Timestamps: 25:26-30:45

• Jared prompts Anthony to share his "most modest dream" for his comedy. Both agree true contentment would be simple financial security (the ability to choose gigs, not chase the cheapest flights, etc.).

  “Right now I can’t plug in my microphone to the computer because…the wire has…only but so many outlets…I just want another surge protector…” – Anthony (25:36) “I just want to be able to do a show that people love and then do 20 cities a year and tape it at the end of the year…” – Jared (27:19)

• They humorously debate whether they’d rather play stadiums, go to the moon, or just have a sustainable career.

7. Winnipeg: The Comedy Festival Odyssey

Timestamps: 31:14-42:14

• Both swap stories about working in Winnipeg, with Anthony recalling his 15-day stint at the Fringe Theater Festival where he stayed with a host family.

  “All people in Winnipeg do is apologize to you for being in Winnipeg…” – Jared (31:19) “I was there in the summer. It was beautiful…It was a lovely town, but they…talk about how bad it is to live there.” – Anthony (33:24)

• Jared offers witty Canadian city archetypes ("Edmonton’s cowboy Canada, Vancouver is vegan Canada, Montreal is douchebag Canada, Toronto is New York").
• Anthony recounts movie nights with his host family and the relative comfort found among “weirdo” art supporters, leading to a brief riff about the importance of eccentric fans to the arts.

  “If you didn’t exist, none of this would work. You just hear the same jokes over and over from TikTok that you saw someone do you know, at the airport…” – Jared (43:00)

Notable Quotes & Memorable Moments

• [03:10] Jared: “When there’s one set of feet in the sand, that was Anthony carrying you with laughter and love and joy…”
• [04:38] Anthony: “I give up on the special…there are better things to do with 45 minutes of your life…”
• [06:07] Jared: “It’s either gay man or Jewish woman…Like, chin out, watching, not laughing, not enjoying, just making sure things go okay…”
• [08:31] Jared: “It’s as if they’ve reached down my throat and grabbed my anus to, like, reverse me inside out.”
• [12:18] Jared: “In Canada, it just felt more normalized that comedian could be a middle class job.”
• [15:20] Anthony: “Do you like Tajin? …It’s such an abrasive taste.”
• [22:09] Jared: “Nuance and context is really not what people are looking for, but people meaning the stupids…”
• [25:36] Anthony: “Right now I can’t plug in my microphone… I just want another surge protector.”
• [31:19] Jared: “All people in Winnipeg do is apologize to you for being in Winnipeg…”

Important Segments by Timestamp

• 02:32 – 07:50: Realities and comedy of self-promotion, PR people in show business.
• 08:07 – 11:38: The pain and artifice of comedian bios.
• 11:38 – 14:44: Comparing the comedy trade in Canada and the US.
• 14:28 – 18:10: Delray comedy culture and Tajin tangent.
• 18:10 – 22:55: Personal branding vs. “team” comedy and the flats vs. drums metaphor.
• 25:26 – 27:39: Modest dreams and financial security in comedy.
• 31:14 – 42:14: Anthony’s stories from Winnipeg and the goofiness of comedy festivals.

Conclusion & Call to Action

Jared wraps the episode by urging listeners to check out Anthony DeVito’s newly released special “Straight Hoopin’” on YouTube ([link in episode description]), emphasizing how early views, likes, and subscriptions make a critical difference to indie comics. They close on the note of gratitude for the quirky, dedicated fans who keep stand-up alive, and the modest but deeply meaningful goals they continue to chase in their careers.

Listen to this episode if you want:

• An insider’s comedic take on the grinding realities of DIY comedy
• Unfiltered conversation about PR, self-promotion, and life on the indie circuit
• Quippy riffs on Canadian culture, food trends, and Midwest art supporters
• To support an indie comedian (watch "Straight Hoopin’" on YouTube!)

Links:

• Anthony DeVito – Straight Hoopin’ Special (YouTube)
• Follow @jtrainpodcast and @anthonydevito_ for more