September 9, 2019

From Hustling Dice to the Heights of Global Fashion: The Dapper Dan Story

by Without Fail

Background show artwork for Without Fail

Dapper Dan made a name for himself as one of Harlem’s premier fashion designers in the 1980s, creating unique leather designs covered in counterfeit logos from brands like Gucci and Louis Vuitton. But when the fashion houses found out, they shut him down. So how, 20 years later, did Dapper Dan make it to the top of the world that put him out of business?

Without Fail is hosted by Alex Blumberg. It is produced by Molly Messick, Rob Szypko and Heba Elorbany and edited by Alex Blumberg and Devon Taylor. 

Music and mixing by Bobby Lord.

Where to Listen


ALEX BLUMBERG: From Gimlet, I’m Alex Blumberg and this is Without Fail, the show where I talk with artists, athletes, entrepreneurs, visionaries of all kinds, about their successes and their failures, and what they’ve learned from both.

Now, when my guests normally join me for interviews at the Gimlet studios here in Brooklyn, they usually don’t have to worry that much about their outfits. This is a podcast, after all. But my guest today showed up in an outfit that was, frankly, a tragedy to have wasted on a podcast: a floral patterned silk shirt, checkered pants, a belt buckle in the shape of a dragon’s head, and to top it off, a pair of oversized snakeskin sunglasses. 

DAPPER DAN: 'Cause I was coming to Brooklyn I wanted to be fancy. 

ALEX BLUMBERG: [laughs] You are fancy. That is a ...

DAPPER DAN: Absolutely.

ALEX BLUMBERG: Is that a Dapper Dan original that you're wearing right now?

DAPPER DAN: Yes, it is.

ALEX BLUMBERG: It's amazing.

DAPPER DAN: Tools of the trade. Tools of the trade.

ALEX BLUMBERG: My guest today on the show goes by the name Dapper Dan. And that boldly patterned shirt he’s wearing — he designed it, in partnership with the high-end fashion label Gucci. 

And the fact that he is now, at age 75, working with a luxury fashion house like Gucci is something that probably no one would have predicted three decades ago when he was in the early stages of his fashion career. Back then he worked on the fringes of the fashion world — in fact, for a while, he was the go-to stylist for many of New York City’s most notorious gangsters.

But his early career came to a halt, when the world of high fashion, the world he now calls home, came after him, and put him out of business.  


I talked to Dan about his transformation from a fashion outlaw, to a Gucci insider. From street hustler to someone regularly name checked in rap songs by Jay-Z, Fat Joe, Missy Elliot and many others. 

And one of the many things that struck me during the conversation, was how Dan’s story serves almost as an allegory for the fate of the neighborhood he’s called home his entire life: Harlem. A neighborhood that was seen as the hub of black culture in New York City, then fell on hard times, weathered the crack epidemic, and is now going through another transformation, a messy blend of economic development, and gentrification. Dan’s story also charts that epic course. And just a quick warning before we get started, there is some swearing in this episode. 

Dan was born in Harlem in 1944, grew up poor, one of seven children. His father only had a third grade education, couldn’t really read, and worked three jobs to make ends meet.  

DAPPER DAN: Let me tell you something… one of the turning points in my life was when my father was gonna buy me a suit from Ripley's Department Store. And we went into the store ...

ALEX BLUMBERG: What was -- what was the suit for?

DAPPER DAN: The suit was for Easter. It was gonna be an Easter suit. It was charcoal brown with gray pinstripes. I never forget that suit, right? So we go to Ripley's, and he's gonna buy it on credit, right? So I look at the contract that my father had and I said, "Daddy, they gonna charge you two and a half times what this suit cost." I had just learned how — I was in eighth grade, going into the eighth grade, learned the mathematical calculations for interest. And I told my father, "This is gonna cost you two and a half times," right? And my father said, "Boy, don't you know you can read." And tears welled up in his eyes. And the expression on his face, I could see it every day like it happened yesterday. He say, "Boy, you could read." Do you know what that means do you know how powerful that is? You know? He understood the power of information. And that's what it was. It was information. I realized how important reading was. Anything that I wanted to be that could free me up from the situation that I'm in was through the power of reading. And so I read my way through everything in everything and out of everything.

ALEX BLUMBERG: Dan’s love of reading served him well in school. But it also served him well in another place, outside on the streets. See, as a teenager, Dan became enthralled with the neighborhood dice games. Back then, Dan says, every two or three blocks In Harlem, you could find groups of men betting on dice games and the hustlers trying to take their money. Dan started skipping high school to try to win money at these games. He learned everything about the dice game that he could, how marks were called vics, short for victim. How 7 was the likeliest roll, followed by 6 and 8, and how you always needed to keep the odds in your favor. And at a certain point, he felt he’d learned all he could from the streets. 

DAPPER DAN: What I did was I exhausted all the street education that I could get —


DAPPER DAN: And then I look for books that possibly would tell me about it.


DAPPER DAN: And the books was -- the master books was Hustlers and Con Men. And then for my profession, which is gambling, the world authority on it, on the level that I was gambling was John Scarne. John Scarne was the advisor to the United States government on professional gambling and casinos and everything. And he wrote the books that will be considered the Bible.

ALEX BLUMBERG: What books were those?

DAPPER DAN: Oh, John Scarne on gambling. John Scarne on dice. John Scarne on cards.

ALEX BLUMBERG: Is it -- this -- the book, was that something that you -- that was known? Like...

DAPPER DAN: Nope, none of the older guys who taught me things ever mentioned that book to me. You know, and sometime you just -- you come across information so amazingly.

ALEX BLUMBERG: So what was your life like? At that point? 

DAPPER DAN: Oh, I'm poor as hell. That was the purpose of learning the game. You know? To escape poverty.

ALEX BLUMBERG: Yeah but so once you had learned it though, did that…

DAPPER DAN: Oh, once I learned it, I became like -- a master Sol. If you rise to a certain level, you become what is known in the street as a Sol. A Sol is a name that derives from the -- from the scriptures, the Bible —


DAPPER DAN: As the wisdom of Solomon. So the players looked up to the Sols. The Sol is the king player. So I got known in Harlem because of my skills as a player who became a King Sol and mastered the game. 

ALEX BLUMBERG: So what -- give me an example of like I'm just a regular -- I'm just a regular person in the neighborhood and I -- I walk by a crap game and I'm not like a -- I'm not a professional, I'm not -- I'm just like a normal ...

DAPPER DAN: You're a vic.

ALEX BLUMBERG: I'm a vic! I would definitely have been a vic. That's the role I was meant to play. So I'm a vic, I just got paid, whatever. I've got my -- I'm ready -- I'm ready to have some fun. I go. How ...what...

DAPPER DAN: What would I do to entice you?

ALEX BLUMBERG: Yeah. What do you do?

DAPPER DAN: First of all, all con games, right, is based on some kind of greed within you.


DAPPER DAN: So you use that against the vics, you know what I'm saying? When you hear gambling, that's a misnomer in people's head. Because they think that -- the first thing they think is, luck. But Sols know that gambling is based on the law of probability. I never would place a bet when the dice first come out. I always wait 'til the dice catch a number. And then when you catch the number, I bet him he can't make that number, right?

ALEX BLUMBERG: So people -- so you'd wait for somebody to get their roll. They'd bet, and then they'd get the roll that they bet on. And so then they collect some money. And then you would go up to them and say, "I bet you can't do that again."

DAPPER DAN: I bet you can't make that before you throw seven.

ALEX BLUMBERG: Uh huh. [laughs] Right.

DAPPER DAN: You know?


ALEX BLUMBERG: So, okay, so at this point, when you're a Sol, when you'd -- you'd achieved Sol status. 


ALEX BLUMBERG: How much were you making?

DAPPER DAN: Like, um... I used to have $10,000 in my sock. That was the -- that was the extra money I have, you know? And then I have money in my pocket just to entice them to play. 

ALEX BLUMBERG: So you're walking around and you have $10,000 on your person... How did it feel to have, have money?

DAPPER DAN: Let me tell you something. I'm the first generation of the great migration that came from the South. And this is what makes me who I am today. When you look at the slave trade, how we were captured in Africa, and then we had to survive the middle passage. Then you think about the 350 years of slavery, 375-400 years of slavery that they had to endure. Then you think about the fact Jim Crow, reconstruction. And -- and I look at my parents' life and I think about what they must've gone through. My father's father was born a slave. And my father was born in 1898. That's 33 years after emancipation proclamation. And my father left home at 12 years old, and he came north to make it on his own. You know, I mean... I always had hand-me-down clothes, holes in my shoes, and we had to be innovative. And to be innovative, we used to put paper in our -- in our shoes to cover the holes. And so then we had to be more innovative because the paper would wear out too quick. And we start putting in linoleum. So that's who I am. So … [sigh] How did it feel to have money... Secure. Comfortable. But um, I think the -- the biggest thing about having money is the transformative things that the money does. Not just having it, but what it does. It gets you clothes. It gets you cars, it gets you shiny things, you know? So it's the shiny things in life. If you are born with a certain social structure, the shiny things mean a lot, because with the shiny things, you can equate yourself with people who are so-called better than you are.

ALEX BLUMBERG: So the -- the -- the Sol period of your life, how long did that last?

DAPPER DAN: Never -- it never ends. 

ALEX BLUMBERG: [laughs] But...

DAPPER DAN: I'm Sol-ing right now. You think I'm here by choice? You think I woke up and said, "I want to hang out with you?" I'm Sol-ing right now. It never ends, man.

ALEX BLUMBERG: And what -- what does that make me? Am I a vic or am I, like, a -- am I an accomplice in this con? [laughs]

DAPPER DAN: No, you -- you part of the tools of the trade right now. And I'm gonna fashion you and use you like Sol's lute.

ALEX BLUMBERG: As long as I’m not a vic.

DAPPER DAN: You know, I mean we all -- we all Sols to some degree. Now we look at your credentials and see how far you got and say, "Yo, man. Homeboy's sollin in the radio game."


ALEX BLUMBERG: Dan kept sollin’ in the dice game throughout the 60s and 70s. He’d cycle through different corners all through Harlem, using probability, sleight of hand, and loaded dice to his advantage.

And part of the reason Dan was winning so much money, carrying 10,000 dollars around in his sock, was that at this time, the heroin trade was booming in Harlem. Money was pouring into the criminal underworld. So Dan wasn’t just playing dice against easy marks anymore...he was also playing drug dealers who had extra cash to gamble.

As Dan’s winnings grew, he was able to start buying the flashy clothes that seemed so out of reach on that shopping trip with his father. Pretty soon, his outfits earned him the nickname “Dapper Dan.”

But Dan was also starting to see the darker side of his line of work. His favorite dice partner got addicted to drugs. And Dan realized that some of the drug dealers he was hustling were betting with money they owed other people. If they lost that money to Dan, they could get killed. 

DAPPER DAN: I justified it because even -- I was on a spiritual path and I say, well, I'm gambling because I know I'm breaking dope dealers and they hurting the community.

ALEX BLUMBERG: So I'm taking -- I'm taking money from bad people in other words, I'm not taking money from, like, upstanding people.

DAPPER DAN: Yeah. It's kind of like the Robin Hood thing.



ALEX BLUMBERG: That's what you're telling yourself.

DAPPER DAN: I'm-- that's what I'm lying to myself about, you know? So I'm seeing how this is transpiring in my life, right? See, and I'm -- and I'm seeing who I'm surrounded by, I'm not happy with them. I don't like the conversations they have. I don't like the life they lead. I'm just there to break them, you know? I'm placing myself in a daily hell, you know? For the sake of this money. So I don't really want to do that no more. So I'm weeding myself off that. So I'll say, you know what? I'd rather do something that makes people feel good and ain't gonna hurt nobody. I'd rather sell clothes.

ALEX BLUMBERG: And how -- why clothes?

DAPPER DAN: Why clothes? Because clothes, nothing is more transformative than that. Kind of like Genesis, you know? Adam messed up, got caught. First thing he did, he went and got a loincloth.

ALEX BLUMBERG: [laughs] Transformation.

DAPPER DAN: Transformation.

ALEX BLUMBERG: I'm a new man, God.

DAPPER DAN: Yes. I have covered thy sin. 


ALEX BLUMBERG: Uh huh. So, so there's a picture I want to show you. It's a picture of three people in front of -- in front of a store window. The store window says "Coming Soon, Dapper Dan's."


ALEX BLUMBERG: Ladies and Gentlemens' Boutique.


ALEX BLUMBERG: And do you remember that picture when that picture was taken?

DAPPER DAN: Yes, exactly. It was hot. We was working around, I was just setting everything up, show them how the store was going. So I took my suit jacket off and my tie off. 

ALEX BLUMBERG: So this -- at this point, how old are you? Where are you? How old are you in that picture?

DAPPER DAN: Oh, let me see. I've gotta do the math now. Let's see. I opened that store up in 1982. So I'm like 40. Around 39-40.

ALEX BLUMBERG: 39-40. And what's your state of mind in this picture? You have a, um, it seems like you have a pretty big smile on your face. What are you feeling?

DAPPER DAN: I'm feeling like "Yo, I'm making it happen. I'm making it happen, man." That picture is the beginning of a new episode in my life. 

ALEX BLUMBERG: Dan opened up the shop, hired an in-house tailor to create high-end custom leather jackets. But it wasn’t quite the new episode he was hoping for. His reputation as a street hustler was still well-known around the neighborhood, and the drug dealers who knew Dan from all those dice games, they quickly became his loyal customers. So many of the middle class professionals in Harlem steered clear of the store.

And Dan was left to cater to his primary customer base. He kept the store open 24 hours a day for hustlers who wanted to drop by after a big night out, or didn't want to be seen during the daylight hours. And business was pretty good, but it really took off one day when one of Dan’s customers gave him an idea.

DAPPER DAN: The major drug dealer in Harlem at the time, Jack Jackson. He was one of my prime customers to come to my store. So one day he comes in the store and he has a little pouch. You know, like ...

ALEX BLUMBERG: Like a fanny pack, or ...

DAPPER DAN: Like a fanny pack. Just slightly bigger. And nothing but hundred dollar bills in it. Everybody's looking at him, admiring the bag.And everybody got excited, because it was a Louis Vuitton bag and people was -- really wasn't exposed to that at the time. And, you know?

ALEX BLUMBERG: They're excited about the hundreds, but they're also excited about the bag that they're in.

DAPPER DAN: Because they know Jack, and if he got something, then it must be expensive.

ALEX BLUMBERG: That's the shiniest of the shiny objects.

DAPPER DAN: It's the shiny things, yeah. And so I looked at that bag. I say, "They -- they excited about that bag." I say, "Wow, that bag ain't nothing but five dollars worth of vinyl." I say, "What is it about that bag?" And I’m also reading all kind of spiritual books, right? You cannot study religion without studying symbolism, if you want to go to the roots of religion.


DAPPER DAN: So I say, you know what? It's the symbols. 


DAPPER DAN: It's the symbols. I say, "Imagine if I can have them walking around looking like that bag. 

ALEX BLUMBERG: Them meaning your -- your customers.

DAPPER DAN: Yes. And that's when the brainstorm took place. If they are happy with a little bit of logos, a little bit of symbols, I give them all the symbols in the world. If one is good, a lot is better than good. And that's the idea. So I say, "I'm gonna find out how to replicate them symbols in my own way and turn them into garments." Which none of them luxury houses was doing, you know? So what I ended up doing is teaching myself how to print on leather, started teaching myself textile printing. Start going to trade shows that specialize in textile printing. Reading books on textiles, everything I could find. I go to factories that did textile printing. If they didn't let me in, like I'd wait 'til they close and I go through they garbage.


DAPPER DAN: Actually. Yeah. It was all footwork. Library work. And so eventually I taught myself that.

ALEX BLUMBERG: And you would just buy big bolts of leather? What are the ...

DAPPER DAN: Yes. No, you buy skins of leather. I bought Japanese plonge leather.


DAPPER DAN: Yeah. And um ...

ALEX BLUMBERG: And what are you printing on it?

DAPPER DAN: I'm printing Louis Vuitton, I'm printing Gucci, I'm printing Fendi. I'm printing Polo, you know? Anything. All the, all the major brands.

ALEX BLUMBERG: Now technically that's a crime. Right? Did it feel like -- did it -- what did it -- did it feel like ...

DAPPER DAN: You missed your history lesson. Bringing me here was a crime.

ALEX BLUMBERG: Right. Right. [laughs] Yeah. So no, it did not feel like a crime.

DAPPER DAN: No, it did not feel like a crime. Besides, I was using my own creativity, and I was just implementing within my creativity their trademarks, you know?

ALEX BLUMBERG: Describe what they look like. Those first couple of designs.

DAPPER DAN: Okay, you see a leopard, and you see the spots? That's what it looked like. Just imagine an outfit as looking like a leopard and it got spots all over it. And imagine if you never saw a leopard before with spots. That's what it was like.

ALEX BLUMBERG: The store racks at Dapper Dan’s filled up with unique luxury creations you would never find on Madison Avenue, like reversible coats with mink on one side and leather covered in Louis Vuitton logos on the other. 

And with major drug dealers like Jack Jackson wearing his designs, Dan’s business took off. He had to hire more tailors to keep up with demand. And then, a few years after Dan opened his store, crack cocaine hit New York City. Unlike powder cocaine, crack was cheap enough for just about anyone to afford. And sales of the drug skyrocketed, which meant that drug kingpins were even more flush with cash than before, and looking for someplace to spend their growing fortunes. Dapper Dan’s became even more popular.

DAPPER DAN: I'm only catering to gangsters, right? So one guy come, they getting ready to go to a major event. So he buying jackets and stuff for his crew. He spend $16,000. The next crew from his area come and say, "What did he spend?" I say, "He spend $16,000." They say, "I'm a spend $18 to 20." Next crew came -- this is an actual story. The next crew came and asked me what they spent, and he spent $23,000, you know?

ALEX BLUMBERG: And -- and they're just walking out with, like, jackets. Yeah.

DAPPER DAN: This is like a competitive business. Who can get the flyest, who can get the most logos on their things, you know? It didn't stop with the clothes. It extended to their furniture and their cars and whatever they could think of. They would say, "Well, he got a cover for his Jeep. A Louis Vuitton, Gucci, MCM cover for his jeep." They'd say, "I want you to do my whole jeep."

ALEX BLUMBERG: What do you mean, do the upholstery inside the jeep?

DAPPER DAN: Yes. And the roof of the jeep and the inside of the jeep. The whole jeep. And I would park my jeep in front of the store. I had a red jeep with red and white MCM interior and red and white MCM roof, you know? And when you took that roof off it had a little sun cap and that was red and white MCM. And I parked that in front of the store, I had a Mercedes Benz, right? And I had that all Gucci-ed out. And I parked that in front of the store.

ALEX BLUMBERG: [laughs] That's amazing. That's amazing. So that was like advertising.


ALEX BLUMBERG: Dan’s tailors were on call around the clock, as dealers tried to one-up each other with new custom designs. But as crack brought more money to the store, it also raised the stakes of the drug trade around Harlem. Gangs were getting more violent, the homicide rate in New York City was on the rise. For Dan, this meant that the needs of his customer base were changing. And so, he adjusted his product line accordingly. 

ALEX BLUMBERG: I heard there's -- there's something -- you had a garment called the snorkel?

DAPPER DAN: Yes, the snorkel.

ALEX BLUMBERG: Tell me about the snorkel.

DAPPER DAN: The snorkel was an amazing coat because, um, it was the ideal winter coat, you know? It was a puffy coat, it made you feel warm, you know? And um, had, like -- the hood had raccoon, really fluffy raccoon collar and then it had the logos, the Louis Vuitton logos all over it. Soft plonge leather. And the same colors as the original Louis Vuitton's, with chocolate and the rust and the green lettering, you know? Army green lettering. And so it was an amazing piece of work. And not only that, for the hustlers for extra money, I would line it inside the lining with bulletproof material.


DAPPER DAN: Yeah. So -- and material that whenever they came in to get them jackets, I would tell them, okay, so I wouldn't have no repercussion. I let them go on the roof, show them the material and again let them shoot the material.


DAPPER DAN: Yeah. Could you imagine selling somebody a coat and then they go out and a bullet goes through it? No, I like for them to learn what they had when they leave the store.


DAPPER DAN: Because the bulletproof material comes in three levels, level one, two and three. So they get the chance to determine, you know, which -- what firearms they think they might need to resist.

ALEX BLUMBERG: Wow. Wow! Do you know, did you ever get word back that it had actually saved somebody's life?

DAPPER DAN: Um...I've never got the opposite back.

ALEX BLUMBERG: So you're -- were you scared ever, working with, like, the clientele you were working with?

DAPPER DAN: Are sharks afraid of sharks?

ALEX BLUMBERG: You're asking a vic here. So I don't know. 


DAPPER DAN: No, no...

ALEX BLUMBERG: I don't know what sharks feel. You tell me. Are sharks afraid of other sharks? 


ALEX BLUMBERG: If I was a shark, I might be afraid of other sharks.

DAPPER DAN: Well, you would -- no. Well, you shouldn't be in the water.

ALEX BLUMBERG: [laughs] I think we've established that. So the answer is no. You were not afraid.


ALEX BLUMBERG: No. How could you not be afraid, though? Like, isn't -- isn't there just like the threat of violence is, like, part of that whole situation.

DAPPER DAN: You accept -- you accept all of that. You accept all that. You accept all that. You live with it every day, you know? You live with that every day, so you don't even think about that. You already prepared for that. I was preparing for that from a little boy coming up. This is -- this is the world I've seen, you know?

ALEX BLUMBERG: After the break, Dan comes up against an entirely different threat than the criminals: the law. And he faces off against a future justice of the supreme court. That's coming up. 

[Break 1]

ALEX BLUMBERG: Welcome back to Without Fail and my conversation with fashion designer Dapper Dan.

Throughout the 80s, Dan’s business kept growing. He moved from a simple storefront into a three-story building, with his own printing warehouse nearby. 

But Dan hadn’t just opened the store to make money. He’d also seen it as a way to escape the streets. And on that front, things weren’t going so well. 

ALEX BLUMBERG: At the peak of the store, at the peak of the store's success, on a personal level. Like, what's your life like? What -- where are you living?

DAPPER DAN: I hated it.


DAPPER DAN: Hated it. Felt trapped. I'm open 24 hours a day. If you look back then at my pictures, I look older then, than I do now. My grandkids tell me, they say, "Dang, Papa. You look -- you look older then." It's the state of mind that certain types of spaces will put you in. You know?

ALEX BLUMBERG: What was the stress?

DAPPER DAN: The stress is just dealing with people who are not on the same vibratory plane you're on, man. That's tormenting. All my friends were major drug dealers, so I didn't want to have no contact with them, right? Even though they was in and out. But socially, I didn't have any contact with them.

ALEX BLUMBERG: It sounds sort of lonely.

DAPPER DAN: It was lonely as hell, man. It was a -- it was a bad place, you know? And it was right at the height of the crack epidemic. And I'm seeing people being destroyed right in front of my eyes, you know? And so, and I saw it strike people so close to me that I could no longer trust, you know? And it was a real, really, really lonely time for me.

ALEX BLUMBERG: Eventually, though, Dan would find some customers on a similar vibratory plane. As the 1980s wore on, hip hop was on the rise in New York City. Up and coming artists tried to tap into the glamour and grit that they saw in the streets. And Dapper Dan’s brash designs seemed tailor-made for this new cultural phenomenon, even if Dapper Dan himself was just waking up to it. 

DAPPER DAN: I grew up in the rock and roll era and Calypso era, Afro-Latino music era. So I had been familiar with genres of music and how they evolved. So when hip hop was starting, you know, I -- I saw the birth of it, and I didn't pay really close attention, but the young guys that I had working the store say, "Dap, you know what it is? It's Saturday night, man. I can listen to --" and they used to tell me about the hip hop show. And I would listen in to it with them. And then the ...

ALEX BLUMBERG: The hip hop show on the radio, you mean?

DAPPER DAN: Yeah, on the radio. And it only came on once a week, late at night, yeah? And then they start coming in with the gangsters, you know?

ALEX BLUMBERG: The rappers.

DAPPER DAN: Yeah, the rappers always wanted to be like the gangsters. So they would -- they started coming in with the gangsters and that's when I start familiarizing myself with them. And so when -- I think the first one came in was LL Cool J, Jam Master Jay, Run DMC, like gangsters was buying them stuff. So now there's a shift, right? So the dark side, the gangster side of the culture imploded. And then in the process, hip hop was expanding. So now, the hip hop artists are the major ones with the money, so they -- they done supplanted the gangsters.

ALEX BLUMBERG: Dan embraced this new customer base - he enjoyed talking to these young upstart musicians more than he did talking to the street hustlers. His favorite, he says, was Biz Markee. Dan’s clothing designs made it onto the covers of iconic records like Paid in Full by Eric B and Rakim. It felt like Dan’s dream of putting distance between himself and the streets was finally in reach. But then something happened that threw it all into jeopardy. It started one night, in 1988, when a very famous boxer — and a regular Dapper Dan customer — came in to pick up a custom jacket. 

DAPPER DAN: So Mike Tyson comes to the store all the time. Now, Mike Tyson is the first super athlete of the hip hop era.


DAPPER DAN: You know?


DAPPER DAN: So -- and he comes from Brownsville. 


ALEX BLUMBERG: Brownsville, a neighborhood in Brooklyn, right?

DAPPER DAN: Yeah. So he has the gangster element, the hip hop element.


DAPPER DAN: You know, he's this super guy. Superstar, right? So he comes to the store and cool guy. Me and him tight. Friends to this day. So Mike Tyson he wants to get a jacket made, you know, from a popular rap song, “Don't Believe the Hype.” And so I'm making him up that, cause he's -- there's a lot of publicity going on, bad publicity. So he said, "Dap, I want you to make me up this jacket, man. Don't Believe the Hype." So I make him up this jacket. He's told me he's coming, like, 2:30 in the morning, but low and behold, he comes at 3:30 and one of his arch -- to this day, enemy comes in the store, Mitch "Blood" Green. And Mitch "Blood" Green say, "Mike, you know you ain't beat me that night, man. Mike's like, "Come on man."

ALEX BLUMBERG: This was another boxer, they've had a fight, and that -- that Mike Tyson won. So the boxer, this boxer ...

DAPPER DAN: Yeah yeah. So Mike says, "Shake my hand, man. Shake my hand." So they shake hands. Then Mitch Green just gets really belligerent inside the store and Mike just walks out. Mitch Green follows him outside the store, and he rips Mike Tyson's side-view mirror off the car. Not just any car, a Rolls Royce. And Mike decks him. So you know, Mike Tyson knocks him out in the street. Bloodies his eyes, and... The next day it's in all the newspapers. Mike Tyson knocks out Mitch Green in Dapper Dan's Boutique. 

ARCHIVAL REPORTER: The night manager of Dapper Dan’s boutique says Mitch Green was looking for trouble. But a number of nagging questions won’t go away. Why was the world heavyweight champion shopping in Harlem for a leather jacket, ironically embroidered with the phrase don’t believe the hype, at 4 o clock in the morning... 

DAPPER DAN: That was followed by the next Monday, the first Monday after that there. Um, Monday Night Football. And you know how they have the aerial crew up there in the helicopter? And so they cracking a joke. "Oh yeah. Somewhere down there is Dapper Dan's 24-hour boutique where Mitch Green got knocked out by Mike.” Now I got all this publicity.

ALEX BLUMBERG: You're on Monday Night Football?

DAPPER DAN: Monday Night Football. You know, that was so sensational. My landlord who owned the building, he called up, he say, "How did you do that? How did you arrange for that publicity?" I said, "Man, I ain't arrange for no publicity." He said, "Man, you -- you so popular now that people don't even believe that I own the building that you have the store in."

ALEX BLUMBERG: So this should be a good thing, right? Like, this is what every store owner wants is free publicity.

DAPPER DAN: Yeah, yeah. But for me it had the opposite. It made me the most popular guy in the world in the streets, and the most infamous in the fashion world. Now I'm on the radar. I was under the radar. Now I'm on the radar. And that's what led to all the publicity that involved the brands being aware. They say, "Who -- what the hell is a Dapper Dan?"

ALEX BLUMBERG: Those brands that were asking “what the hell is a Dapper Dan?” were seeing in the news footage around this time, some of Dan’s designs festooned with their own intellectual property. And so, Dan says, companies like Louis Vuitton, and Fendi got court orders, and started raiding Dan’s store. 

ALEX BLUMBERG: What do they do when they raid? What are they doing?

DAPPER DAN: They just -- they just spread out and take it -- and commence to take anything that they see with labels on it.

ALEX BLUMBERG: Take it. And just they take it off the rack and then put it in -- what do they do?

DAPPER DAN: Yeah, put it in, like, their little vans they come with, the little small trucks. And, you know, they go on a raid. So lo and behold now, MCM had been raiding me, Gucci never raided me. MCM raided me and Louis Vuitton did, right? But, um, one occasion when Fendi came in, the lead lawyer for Fendi was Sotomayor. Sotomayor who's one of the justices of the Supreme Court.

ALEX BLUMBERG: Sonia Sotomayor was the counsel for Fendi?

DAPPER DAN: She was the lead lawyer for Fendi when she came in. Very honest lady, I got to give this to her. She said something very -- you know, if it wasn't for them circumstances, I would be like really happy. 'Cause you know what she said when she came? I had just finished a, a Aquascutum-type leather coat, you know, with a tuxedo, black glamour mink collar. And it was Fendi and it was plonge leather. Black on black with black Fendi F's all over it. And she said, "Wow, this guy belongs downtown." 

ALEX BLUMBERG: What do you mean she said this guy belongs downtown? What was that -- what did she mean by that?

DAPPER DAN: Well, she's saying that I -- with the work that I was doing, was that she was amazed by it. Yeah, but she couldn't -- she didn't take me downtown, but she took everything I had with Fendi on it.

ALEX BLUMBERG: [laughs] That's amazing.

DAPPER DAN: Shout out to Sonia.

ALEX BLUMBERG: So these -- these raids are coming. When did you finally make the decision to shut down the store?

DAPPER DAN: So it depleted my funds over a period of time, the raids, I had to buy new machines cause they confiscated all my sewing machines and stuff. So each time after each raid I had to replenish. And over a period of time that took its toll. So I decided to go underground. 


DAPPER DAN: This was probably the most trying time in my life 'cause I lost all my workers, all my machines, right? And so, and to start all over, I had to figure out something. First time in my adult life that I'd like, laid up in the bed, just trying to figure life out. For three months. You know, my daughter said, "Wow, I never saw daddy like this." You know?

ALEX BLUMBERG: After the break, how Dan finally gets out of bed, and eventually, gets into bed with the people who put him out of business. That’s coming up.


ALEX BLUMBERG: Welcome back to Without Fail and my conversation with Dapper Dan.

After spending three months in bed, Dan got back to work. He started out almost literally, where he first began: back on the street, hustling. This time, he was selling knock off Chanel t-shirts on the sidewalk. And he says his first day out, he didn’t sell one shirt. It was a huge blow to his ego, going from a three-story building, fancy cars out front, a team of tailors, to hawking t-shirts off a folding table. Gradually, though, he started getting back on his feet. Selling more clothes, and eventually, set up a sort of underground design and consulting business that ended up doing quite well. He did that for the next two decades.

But while he was out of the spotlight personally, his legend was growing. The hip-hop artists that had frequented Dan’s store had moved further into the mainstream, starring in movies, TV commercials... And they brought along their Dapper Dan styles and Dapper Dan memories. And a funny thing started to happen. A whole new crop of hip-hop stars like Missy Elliott, Fat Joe, and Nas started paying homage to Dan in their music.

[song montage]

DAPPER DAN: my name is appearing in all these rap records.


DAPPER DAN: Because I'm at the birth -- I'm part of the birth of the hip hop era. The birth of a new culture, you know? And so you hear a rapper talking about the birth of hip hop. And they all want to connect, you know, to that vein, that major artery.


DAPPER DAN: Ground Zero. They all -- they all want to connect to that.

ALEX BLUMBERG: And that's you.

DAPPER DAN: So guys are hearing about me from original rappers and this -- and the legacy is being passed down, but nobody ever saw my face. None of the new -- the millennials, they didn't know what I looked like. In fact, millennials, they didn't realize 'til, like, two years ago. They say, "Oh, Dapper Dan is a real person? I just thought that was part of the rhyme," you know?

ALEX BLUMBERG: They just thought you were a lyric. [laughs]

DAPPER DAN: Yeah. They just thought it was a way to end the rhyme. [laughs] If I'm the man, I gotta be a Dapper Dan or something like that. [laughs]

ALEX BLUMBERG: And you're still underground at this point?

DAPPER DAN: Yeah, I'm still underground.


DAPPER DAN: You know, and so all of this is happening and I'm saying, "Damn, what's going on here? It's a new world." And fast forward, here we are now in 2017, 2016, there's social media. And then Gucci makes this thing to say ...

ALEX BLUMBERG: And so -- and so...

DAPPER DAN: Hold up.

ALEX BLUMBERG: So here we are in 2017, Gucci comes out, what do they come out with?

DAPPER DAN: They came out with a jacket that's the exact replica of what I made for a famous Olympian, Diane Dixon. And she sees it and people see it, say, "Hold on. Uh-uh. Uh-uh. 

ALEX BLUMBERG: So she -- she posts something on Instagram and Twitter. And here -- here it is. Will you just like -- tell me -- tell me what you see there. What is this?

DAPPER DAN: And so the same jacket, here's Diane Dixon, I made for her. That is uh, Louis Vuitton, super blouson sleeves, right? And with mahogany mink. And they come out with it in Gucci version with mahogany mink and blouson sleeves with the Gucci print. 

ALEX BLUMBERG: And Diane Dixon tweets and posts this on Instagram. And she's got a picture of her in the '80s, and she's got a picture of the model today, side by side. And you see the jackets look identical.

DAPPER DAN: So now I never knew anything about this -- this new powerful voice called Black Twitter. Black Twitter went viral. And it's like the heavens opened up, you know? It's like here there's 20 years of cloudy weather and all of a sudden there's this break in the sky. You know what I mean? You get this glorious light coming out of the heaven, shines right down into this new medium called social media.

ALEX BLUMBERG: [laughs] So how did this reach you? Who -- what, did your family tell you about this? Or did you -- how did you -- how did you ...

DAPPER DAN: No, everybody was talking about it. Everybody's talking about it. Everybody's talking about it, you know?


DAPPER DAN: Next thing I know, we're getting calls from everywhere. We getting calls from, you know, stylists and artists, and everybody is saying Gucci wants to get in touch with you. You know? So my son say, "You should talk to them. Do you want to do some?" I say, "Oh man, I don't believe it. I don't believe none of this." You know, I had this terrible distrust for this, you know, fashion structure. He said, "But dad, they want to do -- they want to do something with you." I say, "Okay, if they want to do something with me," I say, "I got a brownstone in Harlem." I say, "Tell them to come to my brownstone in Harlem." And they came. And they say, when we did that jacket, that was your creation. We did that to pay homage to you." And I'll take that for their word. We just didn't say it, right? But we're here today to say everybody paid you homage but nobody paid you. We're here to change all that. I say, "Where the contract?"


DAPPER DAN: I said, "I don't want no collaboration, I want a partnership." And they gave me a partnership. And they said, "In addition to that, we're gonna give you the ability to do what you've always done in Harlem. We're gonna open up an atelier in Harlem, "Where you can do what you, be creative. But you just use Gucci fabrication. In addition to that, we gonna have a partnership of a collection that's going to go into all the Gucci stores around the world, and you get a percentage of that."

ALEX BLUMBERG: Mhm. There's this -- there's like -- you know, there's a long history now of, like, white-controlled corporations coming in and sort of co-opting people of color. Um, but then there's also this idea that, like, you're taking Gucci at their word that they are paying homage to -- to you and the designs and there -- it is a partnership. But like, that is -- there is this, like, line, right? Like, was that something that you wrestle with? The fear that, like, that, I don't know. I might be part of, like, some sort of PR stunt on their end. Or this is -- this -- this isn't sincere, necessarily.

DAPPER DAN: No. Well -- well, if anyone who would -- who would harness that kind of a feeling don't understand the nature of economics, you know? It’s like, I have a choice. And that choice is, I can start by building from the bottom and think that I can profit off my culture and compete against a multinational corporation. That's not gonna happen, you know? And if I attempted to do that, that would be like taking us back 50 years, because that would be equivalent to what I call Jim Crow economics, because I'm not in the rooms. And so that's -- that's where I am right now. And this is what I'm trying to explain to everybody else. So now, do you boycott and walk away? Now -- this is the -- this is the options you have. You could boycott and walk away and get zero. How rational is that? As opposed to being a part and being in these spaces with these dark faces and being able to make choices and seeing how the dynamics of multinational corporations function.


DAPPER DAN: You know what I mean?

ALEX BLUMBERG: Yeah. So, partnership with Gucci...what does that feel like now?

DAPPER DAN: Um, this is what I've been saying for, like, the last two years. I've been telling my friends, don't get too close to me 'cause if you pinch me and I wake up, I'm gonna kill you. That's what it feels like. It feel like a dream. You know, it's a rainbow.

ALEX BLUMBERG: And what is -- what's -- what's the rainbow? Is it just the -- is it the money? Is it the fact that you're not underground anymore? Is it the fact of the recognition, what is the thing?

DAPPER DAN: The rainbow is recognition, and what it -- not just personal recognition, but the difference that it makes to the community from which it sprang. The fountain from which this golden water came out of. That's -- that's the biggest part of this. This is a luxury brand. This is global. This -- this presence is felt global. I get Netherlands, Australia, China, all these people are conscious of the fact there's a Black guy from Harlem that has done this. And like, I have what we call pen pals in my day. I don't know what y'all call today, followers today. But I have followers in the shantytowns of South Africa. The favelas of Brazil.

DAPPER DAN: Do you know how that feels to touch people who have a life similar to what I have come out of? You know, I grew up swimming in the Harlem River, sewage floating by my face, you know, laughing at it. You could throw a stone from my house and it'll land in the Harlem River. I am the Harlem River. And I always consider myself as being like the Harlem River. Always there, but always moving.

ALEX BLUMBERG: One of the things that we didn't touch on, which I think to me is, like, one of the biggest transformations that you've gone through that we never even talked about, when you're running dice and when you're on the streets and you were, like, running those games, that was all about business, was all about the numbers. As soon as you open the store, I mean, you have to -- you have to manage the store, right? You have to balance the books, all that sort of stuff. But really, what you are -- you have -- you have transformed yourself into, like, into an artist, right? Like, you are making these designs. And I wonder if, when you just described Gucci coming back and, like, the -- the way it felt like the light was opening up, I wonder if it felt like you're -- one way of looking at your life is like it was a continual process of, like, sharing your gift with the world. And this felt like the culmination of that. That now you can share it and the world is welcoming it.

DAPPER DAN: No. No. Absolutely not.

ALEX BLUMBERG: Okay. That's my big theory.

DAPPER DAN: That's the next to the last step.


DAPPER DAN: You know, you white guys will not get this. Do you understand? And let me tell you what that is, right? Um, life has been an abundance for you. You have no reason to question nothing. But we are constantly questioning who we are. So when I started out, right? I started out in a storefront church. All I had and all my parents could give me was the holy ghost. Do you know what that is? You saw the Blues Brothers when the holy ghost hits them and they jumped up and flipped in the air. Do you understand what that is? You have to understand what that is to understand what it means to Black. The Holy Ghost is the purity of what it means to be Black. We didn't have anything else and know what the saying was? That's all right. We got holes in our shoes, but all God's children in heaven got shoes, you know? So we was locked into wait 'til you die before you can get to heaven and get these things, and that sustained us. Do you understand what I’m saying? I know so much about the darkness. You know what I'm saying? You know, I -- and I had all these visions like Jesus in the cave. You understand? All these symbolisms that I'm studying, I'm reading. I'm saying you have to go into that cocoon and emerge from that cocoon and get to a point where you can have a shine that light. And so where am I today? I'm at -- I'm in the prosperity phase of this. I haven't even begin to expound on what this means spiritually. That’s where I’m heading, this is the story I want to tell. This ain't a Gucci story. This ain't a fashion story. Look at this Black guy who ain't supposed to be nothing. Swim in the river with the shit in it. Where we shit. That's where I was, in the river where we shit. You understand what I'm saying? To me that's the cave, you know? And when you come out of that, you emerge from that , you emerge going with your march towards glory? And if you don't tell that glory story, you don't have a story, you know? So that's where I'm at.

ALEX BLUMBERG: Dapper Dan recently created a new program called the Changemakers, which helps black fashion professionals grow their careers inside Gucci. He’s also written a new book, a memoir called Dapper Dan, Made in Harlem

We created a playlist of some of the songs that name-drop Dapper Dan - from artists like LL Cool J, Missy Elliott, Pusha T... You can find it exclusively on Spotify, at That’s

Without Fail is hosted by me and produced by Molly Messick, Rob Szypko and Heba Elorbany. It is edited by me and Devon Taylor. 

Music and mixing by Bobby Lord.

If you like Without Fail, follow us! You can get every episode for free through Spotify, or wherever you get your podcasts. Thanks for listening.