Tiffany Hansen: This is All Of It on WNYC. I'm Tiffany Hansen, in for Alison Stewart today. Tom Delgado finds the funny in history. Delgado is a local comedian and New York City tour guide. He also has a popular YouTube channel, where he takes viewers on neighborhood historical walking tours. His most recent video, Walking Broadway in the Upper West Side: From 72nd to 86th Street. Delgado also hosts history-themed live shows that he calls a lecture at a comedy show.

This Saturday, the 6th, Delgado is hosting his next event in the series called Tom D's Big NY Show at Caveat on the Lower East Side. The show starts at 7:00. It's going to feature guests like Jonathan Mahler, a staff writer for The New York Times Magazine and author of the book The Gods of New York. On my list, that book, Tom. The comedian, Emmy Blotnick. That is the comedian, Tom Delgado, sitting across me right now. Welcome to WNYC.

Tom Delgado: Hey, thank you for having me.

Tiffany Hansen: All right, so let's just talk about this combination of history and comedy. Not a lot of people, maybe Tom Lehrer, I don't know, think about combining the two. How did that idea come to you?

Tom Delgado: Well, it just came to me from being a tour guide. Being a tour guide for many years, your whole idea is just keep people captivated, and just be yourself. If you like to joke around anyway and tell jokes, whatever, then that's what comes out. You talk about something else that interests you in the meantime, which is history. The two just naturally meld together. It's just a way to do both things, continue to do both things for me.

Tiffany Hansen: You were doing tour guides while you were-- tipping the hand here. You used to be a lawyer.

Tom Delgado: Yes, I used to be a lawyer. I used to be a lawyer. That's right. Bury the lede.

Tiffany Hansen: Also known to be a funny occupation.

Tom Delgado: Sure. No, the complete opposite, actually. No. Actually, what ended happening was I started doing a little stand-up while I was a lawyer, and then I hated being a lawyer, so I was like, "I got to get out of this." I saved up money, quit my job eventually, and then I ran out of money. Shock. Then it was like, "All right. Well, what I do now?" It was either go back to law or do something else. A friend of mine was a tour guide, and he's like, "You should do this." Just studying for the licensing exam, I was like, "This is amazing. My job is to learn about New York City? This is incredible." I just fell in love with it. I did it for many years. It was just great.

Tiffany Hansen: I want to talk a little bit about what it takes to actually go through the process of becoming a certified tour guide, but I'm stuck on this Venn diagram between the law history--

Tom Delgado: Don't overthink it. It's going to make your head hurt. It's going to make your head hurt.

Tiffany Hansen: I feel like we should probably just keep moving.

Tom Delgado: [laughs]

Tiffany Hansen: All right, so New York City tour guide. What does that entail to get certified? They don't just hand that out to anybody.

Tom Delgado: Well, I will say just to not go completely over your question that the only Venn diagram with law is research and reading.

Tiffany Hansen: Oh, sure.

Tom Delgado: No problem there. I love doing it.

Tiffany Hansen: Comedy?

Tom Delgado: That's a little different. That's a little bit more of a stretch.

Tiffany Hansen: All three, right?

Tom Delgado: Yes.

Tiffany Hansen: Like, "I don't know where that sweet spot is."

Tom Delgado: Well, I guess I have it now with doing the history and comedy.

Tiffany Hansen: You're the walking embodiment of it.

Tom Delgado: Exactly, the one. The one on the planet. That's right. No, I guess the tour guide thing is they do a test. The Department of Consumer Affairs does a test you got to take, and you study for it. There's a book. It's not that hard.

Tiffany Hansen: Did you take classes?

Tom Delgado: No, you don't have to take classes. I remember I studied for it. I was like, "I got a cram." I did really well, and I was like, "I really overstudied." Let's just say it wasn't the bar exam.

Tiffany Hansen: Yes, right.

Tom Delgado: You take it, and you get it licensed, and then you're basically a freelancer. I worked with so many different companies doing everything. I was on helicopters, doing tours. I did tours for high schoolers. I did tours for the bands that came in for the Thanksgiving Day parade. I did private tours for billionaires from Europe or random things. All kinds of tours in my years of doing it. Yes, you're just a freelancer, really.

Tiffany Hansen: When you talk about the history-- you're doing a walking tour of the history of New York, we're talking--

Tom Delgado: Yes, it's kind of tough.

Tiffany Hansen: Are you like, "Let's start at 16, 25"? [chuckles]

Tom Delgado: Yes, right. "All right, and this tour will last 10 days. You're going to buckle up." No, I guess it depends on what-- you can do a tour of a building, and different people are going to have different things to say about it. It's the same thing. I guess every tour guide has a different history. It's rooted in facts, hopefully. Yes, you can tell a different story, what you focus on, and what stories you tell.

Tiffany Hansen: Do you decide before you've got the billionaire from whatever town--

Tom Delgado: Yes.

Tiffany Hansen: Are you thinking in advance, like, "Okay, this is--" Do you research the person? "I'm going to do this thing, and I'm probably going to zero in on this, or--"

Tom Delgado: Not really. No, I just do my own thing. You can tell, too, as you go. I guess from doing stand-up, too, you can get a feel for the audience, what they're responding to, and what they're not responding to. You can pivot as well, but not really. I am always reading and learning about the city, so that helps. No, as far as that, I don't.

Tiffany Hansen: I mentioned this YouTube channel that you have, where it's basically you and a camera person walking around the city. Lots going on. Of course, it's New York City. First question is, how do you stay focused in all of that and not get hit by a car?

Tom Delgado: It's not even so much getting hit by a car that makes me nervous as much as people saying stuff and doing stuff. I don't know. I'm just used to it because I usually talk to my cameraman. That helps. I feel like I'm actually giving a tour for somebody as opposed to just this camera. I also do different types of videos, too. I do the ones like you mentioned, this walking tour, where I literally just walk from point A to point B and point out buildings and talk about the history of that area.

I also do neighborhood histories where I'll stop at different spots in the neighborhood and tell you about each of these spots and tell the story of the neighborhood. I'll do interviews with historians. There's all kinds of offerings, I guess, on the channel. Yes, I guess it's really just a matter of-- I don't know. When you're talking about something you like and you're in something you do that you like, I guess you're more present anyway, right?

Tiffany Hansen: Yes.

Tom Delgado: That's what I was not when I was doing law, so I was not present doing that. I was like, "Well, something's off here. I got to get out."

Tiffany Hansen: The other question I have as you're walking around the city is, any good heckling stories?

Tom Delgado: Oh, man, yes.

Tiffany Hansen: First of all, [laughs] you're a comedian. You're used to it, right?

Tom Delgado: Sure, yes.

Tiffany Hansen: Do you get heckled on the street?

Tom Delgado: Oh, yes. You know what, though? The difference is, though, when you're in a comedy club, you're given a little more free rein to deal with a heckler in a different way, as opposed to in a street with 25 paying customers next to you. I remember once. This is funny. I was ending a tour of Chinatown in Foley Square, which is where all the courthouses are, like the Law & Order courthouse, all that.

I said to my group, I was like, "Okay, so we just walked through Chinatown." It was really cool. "We're now where the courthouses are. This isn't as interesting as before. This is a little more boring, kind of just loose, whatever." There was a woman walking around the tour at the time, and she got upset. She goes, "Boring?" She peeked her head, and she goes, "Boring? This isn't boring. I work around here. This is where the law happens."

I was like, "Yes, whatever." I was trying to deal with it, whatever. Eventually, she goes, "Boring? This isn't boring. This is where Law & Order happens." I was like, "Oh, gosh, this is so annoying." Then I go, "Look, ma'am, I didn't mean any offense by it. I used to be lawyer. It's okay." She stopped, and she goes, "You used to be a lawyer? Looks like things are going really well for you."

Tiffany Hansen: [laughs]

Tom Delgado: She said this right in front of my group, and I was like, "Oh, man." I just stopped because in a comedy club, you deal with that in a different way than on the street. Before I could even say anything, someone in my group just let her have it. It was the funniest thing, and just like, "What's wrong with you? What kind of life do you lead?" This woman left with her tail between her legs.

Tiffany Hansen: All right.

Tom Delgado: Yes, there you go.

Tiffany Hansen: It's rough out there.

Tom Delgado: It is rough out there, man. People like to judge. That's for sure. A perfect person to judge is a lawyer to judge you, so I got judged.

Tiffany Hansen: [laughs] Any famous encounters when you're out and about?

Tom Delgado: Yes, this was funny. I was talking once in Dumbo. I was in Dumbo. I was doing a tour and talk about the neighborhood and how much it's changed. People talk about gentrification. I talk about that on my tour as well. There was this older man just hovering around the group. It's 25 people. I was talking about David Walentas, who owns Two Trees Management, who's built up a lot of Dumbo. He's built up Domino Park, all that. I was going off this whole thing. This older man was just hovering.

Eventually, I go, "Yes, and so the neighborhoods changed a lot," blah, blah, blah." Then this guy peeks his head and goes, "But change can be good, right?" I go, "Yes, I guess. It depends on who you ask." He goes, "Okay." Then he puts his hand out to shake mine, and he goes, "I'm David Walentas. I own the neighborhood," in front of the entire group. The group was like, "Is this a joke?" because I just talked about the guy. Sure enough, it was him. He was just in the neighborhood, and he wanted to make sure a tour guide wasn't badmouthing him, I guess.

Tiffany Hansen: All right, then. [laughs]

Tom Delgado: Yes, there you go.

Tiffany Hansen: Listeners, you can chime in this conversation right now, talking about your favorite New York history, maybe a historical fact about the neighborhood that you live in. You can call us. You can text us, 212-433-9692. Is there a history to your apartment building, your specific block? Maybe a little specific tidbit about New York City history that you'd like to share, 212-433-9692. You can call us. You can text us at that number.

We're talking with Tom Delgado, who is former lawyer, current tour guide/comedian, giving tours of New York City neighborhoods. He also has an event coming up this Saturday. It's called Tom D's Big NY Show. That's at Caveat on the Lower East Side. Just getting back to these tours that you have on YouTube, how did you get the idea to start filming those and put things-- is it just that everybody puts everything on YouTube now, or you do have a specific plan?

Tom Delgado: Well, now, they do. Well, I did initially. It's funny you say that because I started doing them, and this is 2017. I filmed the first one. I did it as a pilot to pitch as a show. This is before all these shows. I pitched it a couple of places. They liked it, but they're like, "Who are you? Why should we give you money?" I was like, "Yes, it's fair point." I just basically went and got a camera and learned to edit and all that stuff. I just started shooting these things on my own, but only one every couple of months, every few months.

I was doing some acting stuff at the time and comedy and everything. It was only really when the pandemic hit that I was able to commit more time to it. I really just went out. I made it as easy as possible. I went out, and I just shot videos of me walking around talking about stuff. They took off because people were in their house, and they wanted to see it. Then after that, it kept growing. I started doing different things with it. It was this little organic thing. The pandemic pushed my hand a little bit, too. It forced my hand.

Tiffany Hansen: Do you think it's hard for people on these tours specifically? I guess I'm thinking more about the tours than your live show. To take the history part seriously, when you're also being funny, does it put a question in their mind, do you think?

Tom Delgado: No, I don't think so at all. I think the difference is if your humor is serving the history, then that's good. I think that only helps when the alternative happens, and you're just trying to run amok and be, "Ha-ha-ha." People are like, "All right, dude, just get to the point." I think that's in anything. If you're giving a toast at a wedding, if you put the funny before what you're actually trying to say, people are going to be like, "What are you doing?" or anything, really. If you're interested in what you're doing or what you're talking about, you can make law interesting and funny. You can make accounting interesting and funny if you really have something to say and are funny.

Tiffany Hansen: There are parts of history that aren't so funny.

Tom Delgado: Yes, that's true. That's very true, I guess, but I guess there are ways to bring it-- History happens, and there are things that happen in the world that are obviously not funny, but there are things connected to those things, like whether it's you personally, your life, how it relates, how other people's life relates to what's happening or whatever that you can, I guess, steer the conversation towards and find some kind of laughter in.

Tiffany Hansen: Obviously, you cover the five boroughs. Are there specific neighborhoods that you tend to go to more often than others? How do you decide, like, "I'm going to research this new part of Kew Gardens," or whatever?

Tom Delgado: Yes. Well, I think it's like with anything. Obviously, Manhattan is so popular, and it's also so concentrated. People forget that, too. You go to the West Village or Greenwich Village. You have historical spots, steps from each other. Whereas if you go to other neighborhoods that are a little more residential, there are bigger streets of Queens and all that. Things are a little more separated that way.

It's easier in places in Manhattan and everything. I've done tours in all neighborhoods. I think if people know what they're getting into when they go to Queens for a tour and they know it's not going to be stopping every two seconds at some place that Bob Dylan hung out, then it's fine. If you can tell the story and keep their interest with something else, then it should be okay.

Tiffany Hansen: We got a text here. "Tom, have you ever given a Staten Island tour? If you would like one, I'd love to practice by giving you one. Love this story. Definitely going to be cramming for the test." Been to Staten Island?

Tom Delgado: I have been to Staten Island, yes. It's interesting. I've done tours. We've gone on the ferry, gone over to, obviously, that area in St. George, and walked around that area as well, the Snug Harbor, all those kinds of cool spots there. The problem with Staten Island is it's humongous, and it's not as easy to get around. It's gigantic. It doesn't have the subway. It doesn't have all these things that make it more accessible, but there are tons of interesting things.

I was just doing something recently on the Conference House, which is super cool down at the south end of Staten Island, which is actually the southernmost point of New York State. After the Battle of Long Island, Edward Rutledge, Ben Franklin, and John Adams went to meet with Admiral Howe to try to hammer out a peace deal after getting completely beat up at the Battle of Long Island. They refused because they wouldn't budge on independence. It was all for naught, like, three hours. It ended.

Tiffany Hansen: Maybe you need those. What are those things that people get on? [chuckles]

Tom Delgado: The scooters? [laughs]

Tiffany Hansen: Yes, the scooters.

Tom Delgado: What are those things with the wheels on them? I don't know. I see these kids running around with them.

Tiffany Hansen: Those kids. You know what I mean.

Tom Delgado: Yes, sure.

Tiffany Hansen: What are those white things that you like--

Tom Delgado: Cars. [laughs] Automobiles, Tiffany.

[laughter]

Tiffany Hansen: All right. I'm going to put you on the spot and say, favorite neighborhood?

Tom Delgado: Oh, man, that's tough. It depends on what you're looking for. People always do this. They'll email me, and they'll say, "Hey, I'd love a tour. What's your favorite?" It depends on what they want. If they want a chock full of history, I like walking around Greenwich Village. There's just so much history there, whether it's cultural, political, social, everything. I tend to like Queens. I love Queens. I live in Queens. If people say, "Hey, I've been to New York a million times. Take me to something I haven't seen," I take them to Jackson Heights or Flushing or Flushing Meadows or those places. Their heads explode.

Tiffany Hansen: Right. Let's bring a caller in the conversation here, Tom. Mark on the Upper East Side. Hi, Mark.

Mark: Hey, how are you?

Tiffany Hansen: Good.

Tom Delgado: Hey.

Mark: I love your show. I was calling because the front of my building on East 77th Street on the Upper East Side was the initial scene for Ghostbusters 2. Sigourney Weaver was standing with her baby carriage, and then, suddenly, the ghosts took the baby carriage down the street, and she was running after it. That was my building's claim to fame. You can see it in the beginning of the Ghostbusters 2 movie.

Tiffany Hansen: Love it.

Tom Delgado: Oh, nice.

Tiffany Hansen: All right, thanks, Mark. I bet you could do a whole tour of Ghostbusters spots.

Tom Delgado: Well, it's funny you say that. I have a video that I did years ago of Ghostbusters spots. It's on my YouTube. It's from years ago. I don't even think it's monetized because I like used pictures. Everything's from it. Yes, I did a video on Central Park West, 55 Central Park West. Spook Central, it was called, the building that's there. The church right next to it is the one the Marshmallow Man stomped. Tavern on the Green is where Rick Moranis ran and slammed on the glass. Over on Broadway in the NoHo area is where Peter Venkman's apartment was. North Moore Street in Tribeca--

Tiffany Hansen: Columbia.

Tom Delgado: Columbia, yes, and then North Moore Street is where the firehouse is. The famous firehouse in Tribeca.

Tiffany Hansen: All right. Before we run out of time here, let's talk about your live show you have coming up on--

Tom Delgado: Yes.

Tiffany Hansen: This is different than the tour.

Tom Delgado: Yes.

Tiffany Hansen: Different, similar. Explain how.

Tom Delgado: It's basically like a variety show celebrating the city through history and culture, or whatever you want to say. I do a little lecture about a neighborhood, like a little tour. I have comedians, I do trivia, and then I interview an expert or a guest, some historian. It's great. I promote their work and everything. I actually really pride myself on having these intellectuals, these academics, and making it digestible, making it easier, more accessible. I've had people talking about fascism. I have people talking about gentrification, and people are laughing through it. Like you were asking earlier, how do you make these things funny? I think if it's just natural and whatever. Those are funny. This week, I have Jonathan Mahler.

Tiffany Hansen: Yes, I was just going to say, you have--

Tom Delgado: Who's great.

Tiffany Hansen: Right, Gods of New York.

Tom Delgado: Gods of New York. He wrote, Ladies and Gentlemen, the Bronx Is Burning, which was one of the first books I read as a tour guide, and it blew me away. I'm super excited to have him. Gods of New York is great.

Tiffany Hansen: Let's get one last call in here. Deidre in Ridgewood. Deidre, you got about 30 seconds.

Deidre: Okay, I'm calling because about halfway through this interview, I realized I've watched almost all of Tom Delgado's walking tours. I watched him before I moved to New York to get the lay of the land. I didn't realize until he started talking about being a former lawyer, because he would joke in the tours or in the videos about, "Oh, I used to be a lawyer, and I can't get my tours anymore." I would think to myself, "I hope this works out for this guy."

[laughter]

Deidre: "These videos are great." Then as I was listening, I go, "Wait, I think I know this," and it's sounds like it is working out.

Tiffany Hansen: Thank you, Deidre. I feel like it's working out.

Tom Delgado: Thank you. Maybe we can clip this and send it to my parents. That'd be a nice gift for them for the holidays. [laughs]

Tiffany Hansen: You feel like it's working out?

Tom Delgado: Yes, I do. I feel like it's working out. Even when it wasn't working out, it was working out because I definitely didn't like being a lawyer. Honestly, I was 25, living in the city. It was nice. I was making money and all that, but I remember looking at people who are now my age at that place I was working and being like, "I don't know if I could ever do that." My mind, my imagination wasn't strong enough to imagine myself at that place in 15 years. It just wasn't an option, so I'm glad I got out.

Tiffany Hansen: Well, everybody's got an itch for history, I think, in this city, especially New Yorkers.

Tom Delgado: Yes, and there's plenty of it.

Tiffany Hansen: Plenty of it. One last little text here. "One time, I was canvassing for Zohran Mamdani in Williamsburg, and Antonio Reynoso stopped us to point out the Coming to America building."

Tom Delgado: Nice.

Tiffany Hansen: There's a New York story. All right, you can catch Tom and his New York stories and his New York history this Saturday, the 6th. He's hosting an event called Tom D's Big NY Show. It's at Caveat on the Lower East Side. The show starts at 7:00. Tickets still available?

Tom Delgado: Yes, those tickets still available, and it's monthly as well. It's the first Saturday of every month at Caveat, so we've been doing it for three years.

Tiffany Hansen: Oh, God.

Tom Delgado: It's a monthly show, and this is the December edition, I guess.

Tiffany Hansen: All right, and your YouTube channel?

Tom Delgado: The YouTube channel is tomdnyc. It's the same as my Instagram. I also have a weekly show, a weekly stand-up show that I've been running for 10 years in the Lower East Side on Tuesdays at 7:30 at Lucky Jack's.

Tiffany Hansen: That's Tom Delgado. Tom, thanks for being with us.

Tom Delgado: Of course. Thank you for having me. It's great.

Tiffany Hansen: Coming up, we're talking the best cocktails in New York. Don't go anywhere. I'm Tiffany Hansen, in for Alison Stewart. Stay with us.