TERRY GROSS, HOST:
This is FRESH AIR. We're going to remember Holly Woodlawn, who died of cancer Sunday at the age of 69. She inspired the first verse of Lou Reed's 1973 hit, "Walk On The Wild Side."
(SOUNDBITE OF SONG, "WALK ON THE WILD SIDE")
LOU REED: (Singing) Holly came from Miami, Fla., hitchhiked her way across the USA, plucked her eyebrows on the way, shaved her legs, and then he was a she. She says, hey, babe, take a walk on the wild side. Said, hey, honey, take a walk on the wild side.
GROSS: Holly Woodlawn was a trans-woman who was one of the last of the Andy Warhol superstars. She made her debut in the Warhol-Paul Morrissey film "Trash," playing the girlfriend of a drug dealer. In this scene, Woodlawn has brought over a prep school boy she's just picked up who's looking to buy some drugs. Woodlawn figures she can get some from her boyfriend, played by Joe Dallesandro.
(SOUNDBITE OF FILM, "TRASH")
HOLLY WOODLAWN: (As Holly Sandiago) Listen, hey, you got anything?
JOE DALLESANDRO: (As Joe Smith) No.
WOODLAWN: (As Holly Sandiago) Because he wants to...
DALLESANDRO: (As Joe Smith) Nothing, nothing.
WOODLAWN: (As Holly Sandiago) He's got bread.
DALLESANDRO: (As Joe Smith) Yeah, I know, but I don't have anything. That's great.
WOODLAWN: (As Holly Sandiago) He's cute.
DALLESANDRO: (As Joe Smith) Yeah, really great.
WOODLAWN: (As Holly Sandiago) Nothing, huh?
DALLESANDRO: (As Joe Smith) Aren't you glad I cleaned up?
WOODLAWN: (As Holly Sandiago) He looks nice. He looks nice, doesn't he?
DALLESANDRO: (As Joe Smith) Yeah, he looks great. He's a little kid, ain't he?
WOODLAWN: (As Holly Sandiago) So what? He's got bread.
DALLESANDRO: (As Joe Smith) Yeah.
WOODLAWN: (As Holly Sandiago) Bread, bread.
GROSS: Recently, Holly Woodlawn appeared in a couple of episodes of the series "Transparent." I spoke with her in 1991 after the publication of her memoir, "A Low Life In High Heels." Woodlawn's birth name was Harold Eisenberg (ph). According to her memoir, the name Holly was inspired by the character of Holly Golightly in "Breakfast At Tiffany's." The Woodlawn part came from Woodlawn Cemetery. I asked her what Harold Eisenberg was like before he became Holly Woodlawn.
(SOUNDBITE OF ARCHIVED BROADCAST)
WOODLAWN: I was, what, shy and skinny, and I had buckteeth and, you know, and gawky-looking and stupid-looking (laughter). I didn't like the way I looked, you know. And then one day, I moved to New York and, you know, and discovered makeup. People started telling me how pretty I was. So, you know, why not?
GROSS: Do you remember the first time you put on a woman's clothes?
WOODLAWN: Well, actually, it came in spurts, you know. As the Lou Reed songs goes, you know, Holly came from Miami. I shaved my legs in - what? - in Atlanta, Ga., and plucked my eyebrows there. And I think in, like, North Carolina I did something else. You know, I put on a blouse. And, you know, in Philadelphia, the land of brotherly love, pantyhose. And by the time I landed in New York City, I was a full-blown woman.
GROSS: What did you like about it?
WOODLAWN: Well, first of all, the fact that, you know, I was more comfortable and the attention that I got.
GROSS: You got more attention dressed as a woman than as a man?
WOODLAWN: Yeah, and I just felt more comfortable, you know, inside, inside, you know, sort of like my soul, so to speak. You know, I felt freer. It was easier for me to speak, just be. And as Harold, you know, quote, unquote, "I just was always nervous," you know.
GROSS: Why did you hitchhike across the USA?
WOODLAWN: Because I only had $11.
GROSS: Why did you leave home?
WOODLAWN: Let's see. You know, I was 15. I was - my parents, they just found out that I was hanging around with the wrong kind of people, you know, in their eyes. You know, they had just discovered that I was gay, and I was, you know, hanging out with these madmen, insane queens in Miami Beach. And they found out. And I had to go to summer school. And I wanted no part of that. And so some friends of mine said, listen, we're going to New York and you got to come with us. It's fabulous over there. The streets are paved with diamonds, you know, that diamond dust. And so I, you know, I said to them, sure, why not? I did. And it wasn't easy at first, but, you know, I sort of stayed on.
GROSS: Well you made a living hustling at first.
WOODLAWN: I did everything at first. I mean, you know...
GROSS: When you were hustling, you were hustling as a woman, right?
WOODLAWN: Actually, no. I was hustling more as a transvestite, you know, in between.
GROSS: So people could tell? They were never, like, surprised...
WOODLAWN: No. Oh, no, no.
GROSS: ...When they found out what was underneath?
WOODLAWN: Yeah, that's why I never got in trouble because, you know, they knew.
GROSS: It's amazing the way you used to travel back and forth between worlds. You know, like you got this job as a salesgirl at Saks. You had modeling jobs in other stores. But you went to beauty school as a man.
WOODLAWN: Yeah, but that was in the beginning when I first was sort of like - I was doing the transition from a man to a female. But I was going to beauty school. I was living in Brooklyn, and I was going to school in Manhattan. And I was living in Brooklyn as this guy's wife and going to school as Harold Eisenberg. And so what I would do is I would take the subway from Brooklyn to New York as a woman, go into the bathroom, change into Harold, go to school, and then do the opposite on the way back. And after a while it just got so tiring that one day I just went to school as Holly. And, well, so much for that. They, you know, threw me out. I was also doing hormones until I had breasts.
GROSS: You were doing hormones because you were thinking of having a sex change operation at the time?
WOODLAWN: Yeah, actually, twice, twice. We saved up the money. And both times I just couldn't do it. I had this money in my hand. And instead of - when was I - John Hopkins Hospital. Instead of going, you know, going through with it, I just decided to go shopping.
(LAUGHTER)
WOODLAWN: I did.
GROSS: Why did you decide not to go through with it after saving and preparing for so long?
WOODLAWN: It's so final. It's just one of those things that, you know, there's no turning back. And I just didn't feel I knew yet what I really wanted to be.
GROSS: Well, looking back now, do you have any regrets about not changing yourself physically?
WOODLAWN: No, not at all, no. I'm pretty much happy the way I am.
GROSS: What have you been doing for money?
WOODLAWN: I was working in a novelty shop as a cashier.
GROSS: Was it an interesting shop or interesting people came in?
WOODLAWN: Oh, yeah, yeah. John Waters used to come in there. Debbie Harry. All my friends would come in and say, Holly, what are you doing here? And I said, well, I'm writing a book.
GROSS: Did you like people to know that you were Holly Woodlawn when you worked in the shop? Or did you want to be more anonymous? Did you ever feel bad about having to work that kind of job?
WOODLAWN: Not really. You know, it was just fun having something to do. But, you know, for the past two years, you know, this book has really taken up most of my time. Of course I lived on the advance.
GROSS: Right.
WOODLAWN: And my parents helped me out a lot, too.
GROSS: You know, it's interesting, you describe in your book how your parents have really stuck with you. I guess there was a lot of friction when you initially...
WOODLAWN: Yeah.
GROSS: ...Ran away from home or hitchhiked away from home, and so on. But you say that over the years they have stuck with you.
WOODLAWN: Oh, yeah, we're the best of friends. My parents just - my father just read the book. He thinks it's hysterical and doesn't believe a word of it.
GROSS: (Laughter) OK, well, I wish you the best.
WOODLAWN: Thank you.
GROSS: Thank you very much for talking with us.
WOODLAWN: It was a pleasure.
GROSS: Holly Woodlawn, recorded in 1991. She died Sunday at the age of 69. Tomorrow on FRESH AIR, I'll talk with Jeffrey Tambor about playing a trans-woman on the Amazon series "Transparent."
(SOUNDBITE OF TV SHOW, "TRANSPARENT")
JEFFREY TAMBOR: (As Maura Pfefferman) When she was little, she used to accuse me of wearing her clothes.
UNIDENTIFIED ACTRESS: (As character) Did you?
TAMBOR: (As Maura Pfefferman) Of course I did.
GROSS: The complete season two of "Transparent" will be up on Friday. Tambor also co-starred in "Arrested Development" and "The Larry Sanders Show." I hope you'll join us. Transcript provided by NPR, Copyright NPR.