All Of It (WNYC) – Episode Summary

Episode Title: Tom Delgado Explores NYC History Through Comedy
Air Date: December 4, 2025
Host: Tiffany Hansen (in for Alison Stewart)
Guest: Tom Delgado (Comedian, NYC Tour Guide, YouTuber)

Overview

This episode features Tom Delgado, a stand-up comedian and former lawyer who's made a name for himself as a charismatic New York City tour guide and popular YouTube creator. The conversation dives into how Delgado combines comedy with NYC history, his journey from law to laughter, favorite urban legends, and the quirky, diverse community that makes city history tours so compelling. The episode also promotes his live show blending historical "lectures" with entertainment.

Key Discussion Points & Insights

From Lawyer to Laughing Tour Guide

• Origin of Combining Comedy & History

  • Delgado's path began with a profound dislike of his legal job, the lure of stand-up comedy, and a fateful push from a friend to become a NYC tour guide.
  • Quote (01:21):
    "Being a tour guide for many years...your whole idea is just keep people captivated...And if you like to joke around anyway...and you talk about something else that interests you...the two just kind of naturally meld together." — Tom Delgado

• Research Skills as a Bridge

  • Skills from law—mainly research and reading—helped, but the primary overlap is passion, not process.
  • Quote (03:03):
    "The only Venn diagram with law is research and reading...I love doing comedy. That's a little different." — Tom Delgado

Becoming a New York City Tour Guide

• Getting Certified

  • The Department of Consumer Affairs issues the tour guide license after an exam; it's not as rigorous as the bar exam.
  • Freelancers can take on a range of assignments—from billionaires to high schoolers, from helicopters to classic walking tours.

• Crafting Unique Tours

  • Each guide offers their own narrative—a blend of historical fact and personal focus.
  • Quote (04:17):
    "Every tour guide has a different history. It's rooted in facts, hopefully, but...you can tell a different story." — Tom Delgado

• Customizing for Audiences

  • Rather than deep-diving into a client’s background, Delgado adjusts in real-time based on audience reactions—a skill borrowed from stand-up.

Filming & Sharing New York’s Stories

• YouTube Channel Genesis
  • Started in 2017 as a TV pilot pitch; evolved into self-produced YouTube histories, exploding in popularity during the pandemic.
  • Delgado offers various video formats: walking tours, neighborhood histories, interviews with historians.
  • Staying focused in chaotic NYC: Treats videos like live tours, directly addressing his cameraman as a stand-in for the audience.
  • Quote (05:34):
    "When you're talking about something you like...you're more present anyway, right? I was not when I was doing law." — Tom Delgado

City Surprises & Humor on the Street

• Hecklers and Encounters (06:29–09:10)
  • Stories of unexpected heckling, both humorous and biting, such as the courthouse worker who mocked his career change.
    • Quote (07:30):
      "You used to be a lawyer? Looks like things are going really well for you." — Anonymous heckler
  • Famous faces: Once met David Walentas—the developer he was just describing on a Dumbo tour.
    • Quote (08:43):
      "He puts his hand out to shake mine and goes, 'I'm David Walentas. I own the neighborhood.'" — Tom Delgado

Humor as a Historical Tool

• Comedy’s Role in Engaging People (11:06–12:31)
  • People take history seriously when humor serves the facts, rather than undermining them.
  • On handling sensitive history: Some moments aren’t funny, but humor can reframe or personalize the conversation to make it more engaging.
  • Quote (11:25):
    "If your humor is serving the history, then that's good. That only helps." — Tom Delgado

Favorite Neighborhoods & Tour Logistics

• How Delgado Picks Locations (12:31–14:32)

  • Manhattan (especially Greenwich Village) is packed with accessible history; outer boroughs are more spread out but equally fascinating.
  • Staten Island tours: Less accessible by transit but home to gems like the Conference House (site of a Revolutionary-era peace attempt).
  • Quote (13:37):
    "The problem with Staten Island is it's humongous and not as easy to get around...But there are tons of interesting things." — Tom Delgado

• Personal Favorite Neighborhood (14:56)

  • Loves Greenwich Village for its density of stories; loves showing seasoned New Yorkers fresh sides of Queens such as Jackson Heights and Flushing.

Fan Engagement & Fun Facts

• Listeners Share NYC Legends (15:35–17:06)
  • A caller shares that their building was featured in "Ghostbusters 2;" Delgado describes a Ghostbusters-themed tour video and other filming sites.
  • Quote (16:18):
    "I have a video that I did years ago of Ghostbusters spots. It's on my YouTube..." — Tom Delgado

Live Show: "Tom D's Big New York Show"

• What the Show Is (17:06–17:53)

  • A monthly “variety show” at Caveat on the LES, blending neighborhood lectures, comedy sets, trivia, and interviews with subject-matter experts and historians.
  • The goal: Make academic or heavy topics fun and digestible.
  • Quote (17:15):
    "I actually really pride myself on having these intellectuals, these academics, and making it digestible, making it easier, more accessible." — Tom Delgado

• Upcoming Guests

  • Jonathan Mahler (NYT Magazine; author of "Gods of New York," "Ladies and Gentlemen, the Bronx Is Burning").
  • Comedian Emmy Blotnick.

Audience Appreciation

• Fan Validation (18:08–18:55)

  • A caller explains she watched his tours to prepare for moving to the city and admires how he shared his journey away from law in the videos.
  • Quote (18:44):
    "I hope this works out for this guy. These videos are great...and it sounds like it is working out." — Deirdre (listener)

• Delgado’s Reflection

  • Quote (18:55):
    "Even when it wasn't working out, it was working out because I definitely didn't like being a lawyer..." — Tom Delgado

Memorable Quotes

• On the fusion of history and comedy:
  "Every tour guide has a different history. It's rooted in facts, hopefully, but you can tell a different story." — Tom Delgado (04:17)
• On handling hecklers:
  "Someone in my group just let her have it. It was the funniest thing...this woman left with her tail between her legs." — Tom Delgado (07:50)
• On pursuing a meaningful path:
  "Even when it wasn't working out, it was working out because I definitely didn't like being a lawyer." — Tom Delgado (18:55)

Notable Timestamps

• 01:21 — How Tom melds comedy and history after leaving law.
• 03:15 — The process and exam for becoming a tour guide.
• 05:34 — Keeping focus amid NYC chaos while filming walking tours.
• 06:35–09:10 — Heckling stories and a surprise encounter with David Walentas.
• 11:06 — Comedy’s function in communicating real history, even hard topics.
• 13:37 — The challenges and gems of Staten Island history tours.
• 14:56 — Tom's favorite neighborhoods to guide.
• 15:35 — Caller shares Ghostbusters filming location trivia.
• 17:06–17:53 — Structure and philosophy of the live “variety show.”
• 18:08 — Listener calls in, credits Tom’s videos for helping her move to NYC.

Where to Find Tom Delgado

• Live Show: Tom D's Big New York Show — First Saturday monthly at Caveat, Lower East Side.
• YouTube/Instagram: @TomDNYC
• Weekly Standup Show: Lucky Jacks, LES, Tuesdays at 7:30 PM.

Tone & Style

Delgado’s style is warm, self-deprecating, and always eager to underline the unexpected in NYC history. The conversation is filled with camaraderie, quick wit, and a clear sense of community engagement—both with live audiences and online fans. The overall tone is informal and lively, emphasizing New York City’s quirks, the serendipity of public life, and the power of following one’s passion into less conventional careers.