Naked Angels’ Merrill Holtzman Reborn as Shtickster Jack Merrill

Jack Merrill is a good actor and a very good manager of

voguish theater companies, but what he’s really good at is positioning himself.

In his two decades in Manhattan,

Mr. Merrill has perfected the Art of Proximity. He’s one of

those people who’s always in the luminous orbit of one rich or famous

person or another-but who does so without guile or sycophancy. Although Naked

Angels, the theater company he co-foundedin1986-which featured Sarah Jessica

Parker, Matthew Broderick, Gina Gershon, Lili Taylor, Marisa Tomei, Rob Morrow

and Fischer Stevens, and had the late John Kennedy Jr. as a board member-is

basically defunct, he has stocked his latest theater troupe, Urban Empire, with

the sons and daughters of the rich and famous: actors Rob Kravis (Henry Kravis’

son), Daniella Rich (Marc and Denise Rich’s daughter) and Linda Powell (she

calls the Secretary of State “Dad”). Board members include Norman Mailer’s son

Michael and David Niven’s granddaughter Fernanda.

Needless to say, most nights he’s out.

“I get invited a lot of

places; I’ve always been lucky that way,” the 37-year-old Mr. Merrill said. “I

think I’m easy . There are famous

actors who always say, ‘I just showed up on time.’ That’s what I do. People

invite me, and I show up and look nice and I don’t complain. And I appreciate

it and I have fun! Then you get invited back. I am extremely grateful, constantly grateful.”

“He’s one of the poorest guys I know who lives the lifestyle

of the rich and famous,” said actress Nancy Travis, who’s known Mr. Merrill

since college. “He’s always calling me to tell me, ‘Well, I just came back from

Aspen,’ or ‘I’m off to so-and-so,

and I’m going here, and I was just at this dinner and that dinner,’ and my God!”

Until this year, Mr. Merrill went by his given name-Merrill

Holtzman. But he changed it to avoid any gender confusion, particularly with

casting agents. “It’s like, enough with the boy named Sue,” he said. His

friends still call him Merrill. In addition to acting in plays, he’s had small

parts on television (a sleazy lawyer on Law

& Order , a blind date on Sex and

the City ) and some parts in films (John Sayles’ Eight Men Out , Neil LaBute’s Nurse

Betty ). Earlier this summer, Mr. Merrill took five one-act plays that first

appeared in Zoetrope: All-Story,

Francis Ford Coppola’s literary magazine, and staged them at Show World, the

porn palace on 42nd Street.

“He just ran with it, as only a person who has a strong sense of what they’re

trying to accomplish does,” said Zoetrope:

All-Story editor Adrienne Brodeur, who will team up with Mr. Merrill again

this fall to hold new fiction readings by actors at the Screening Room in

Tribeca.

But none of the above explains why he’s decided to become a

stand-up comic.

At a recent New Talent Night at Caroline’s comedy club on

Broadway, Mr. Merrill was onstage. “How you doing?

Nice to see you,” he said. “I just want to say that I’m a Greenwich

Village homo. How did this happen? Well, I’ll tell you how it

happened, because all of you sitting in this room tonight are complicit in the

nationwide conspiracy that’s affected my entire

life. It’s the one-dick rule. You know what it is: The guy sucks one

dick-just one- he’s gay. O.K., all right, fine, fine. I sucked one dick. O.K.? One little dick . O.K., it wasn’t that little. O.K., I sucked one big

dick. O.K., I sucked an enormous cock .

So what? So, so I’m gay and I’m out-and I don’t mean out, I mean out , like a social outcast, one of those fuckers on the bottom rung in India.

Give me a pile of cow dung to sleep on, you know what

I’m saying? It’s a nightmare, and it’s my life.”

Laughter-he was winning the audience with the blue material.

“Oh, girls,” he continued. “Girls can eat all the pussy they

want-they’re still straight. Girls can go out and eat pussy breakfast, lunch

and dinner-they’re straighter than ever. Guys, one dick: gay. Gay, gay, gay . Why

is this? Where’s the outrage? I say, why don’t we make it a five-to-10-dick

rule? Why not?”

Caroline’s ended up booking him for two shows, Sept. 25 and

Oct. 29.

I asked him later why he got into stand-up. “I thought, ‘Oh,

that looks like fun, let’s do it,'” he said. “It’s that simple. I saw Jerry

Seinfeld at a benefit, and he was so funny and so simple, I was so inspired, I went and wrote my thing. I’m always telling

jokes anyway. I just took some of them and threw them into an act.”

On a recent Sunday afternoon, Mr. Merrill was in the bedroom

of his spiffy, low-ceilinged basement apartment in the West

Village.  “This is where it all happens!” he said. He

showed off his glass bathroom cabinet. “It’s all laid out very nicey-nicey,” he

said. On a table was a provocative picture of his friend, fashion designer and

former Jerry Seinfeld flame Shoshanna Lonstein. “She has a perfect body,” he

said. On the refrigerator was a picture of himself

with actress and oil heiress Ginny Bond. Above his desk was a photograph of

John Kennedy Jr. and Carolyn Bissette. “She gave that to me,” he said, his

voice cracking. “Quite a couple, huh? I kind of put it

there so they’re like watching over me.”

I asked him what his favorite thing to do was. “I would have

to say, I’m very attracted to people,” he said, laughing. “Sometimes they don’t

find me as attractive as I find them, but I would say that’s the one thing I

indulge in: getting to know people on a variety of levels .”

Sex?

“It’s relatively steady,” he said. “It doesn’t seem to be

diminishing, either.”

Most of his friends are straight. “I’ve never really

understood the gay world very much and never really felt a part of it,” he

said. “Because I’m not sure that there is a way to be a part of it. I’ve always

felt like an outsider in that world, because I don’t really think there’s much

in common there.

“I’ve always been an outsider,” Mr. Merrill said. “But not

because I was gay. I’ve always been an inside outsider, always felt that way. I

belonged everywhere and nowhere at the same time.”

Falling in Love

He was raised in Evanston, Ill.,

by a mother who loved jazz and a father, Jerome Holtzman, who was a well-known

baseball writer. Young Merrill wanted to be an actor but spent more time

playing sports. He barely cracked a book at Evanston High, which he called a

“classic John Hughes, all-American high school …. I would be the perfect mix

between Judd Nelson and Molly Ringwald. I was the debutante who was always in

trouble.”

He had girlfriends and “there were a couple guys around, and

I sort of experienced both sides of the equation by the time I was midway

through high school,” he said. “But I always thought I’d be married with kids.”

Then, as a teenager, he

fell for a guy in an emotional way that he’d never experienced with a girl.

“And I had to pay attention to that,” he said. “I really fell in love with him,

and that was the indicator for me. I

loved girls , but the depth of the way I was in love made me realize that where

your emotional life is, that’s really where your sexuality is.”

At 16, he moved out of his parents’ house. “That was

probably one of the gutsiest moves I made,” he said. “It just wasn’t a happy

situation, although things are fine now.” Lying about his age, he got his own

apartment and a job as a waiter at Barbara Eden’s nightclub in Chicago.

After a year at the University

of Illinois, he drove to New

York and moved into a studio on West

28th Street with a slanting ceiling and big

roaches. He waited tables at the Russian Tea Room; Madonna was the coat-check

girl.

“She had a bunch of shit

in her hair,” Mr. Merrill said. “I also remember she was a bitch.”

He got fired for breaking a Bellini. But he had an uncle in New

York, a successful sculptor and businessman named

Karl Mann. One day they were at Macy’s, and Mr. Merrill mentioned that he had a

birthday coming up.

“We were standing near the men’s department,” Mr. Mann said.

“So I took off my watch and said, ‘I’ll give you two minutes-I’ll give you

anything you want.’ So he grabbed up all these different clothes and threw it

on the counter, and they added it, and it came to about $560. So I paid for it.

A week or two went by, and the next time he came to see me at my studio, he had

this nice jacket on. I said, ‘That’s a very nice jacket.’ And he said, ‘I

cashed in all that trash you bought me and bought a new jacket.’ And I thought,

‘Well, that was a smart thing to do.'”

In 1983, Mr. Merrill enrolled at New

York University.

“I hadn’t really planned to go to college when I got here, but then I found out

N.Y.U. had a great gym and a good acting program, sort of in that order,” he

said. The playwright David Mamet was teaching there and became a mentor. Mr.

Mamet hired Mr. Merrill as an assistant during the Broadway run of Glengarry Glen Ross . “That year, I sort

of met everybody I’d thought I’d ever meet in my entire life. It was very

exciting,” Mr. Merrill said. Mr. Mamet took him to his cabin in Vermont,

told him what to read, taught him how to shoot a gun

and how to produce plays.

He took some acting

workshops; at one, he met Martha McCully, who later was on the board of Naked

Angels and now is an Internet consultant at Gloss.com. At the workshop, Mr. Merrill

told a story about the Christmas he’d given a down jacket to his sister, who

was institutionalized and later tried to commit suicide by jumping off a bridge

in Chicago. But she was wearing the down jacket, which

acted like a life preserver, so she floated and lived.

“That side of Merrill is not really the side that everybody

sees all the time,” said Ms. McCully. “When I saw him up onstage and he told

this story, and I was, like, crying .

I knew I was going to be friends with him forever.”

In 1986, Mr. Merrill co-founded Naked Angels with Jenifer

Estess and other friends; she was then an actor and is now perhaps his best

friend. His uncle provided the acting company with rent-free space in a

building he owned on 17th Street

for a year and a half. “He wheedled it out of me,” Mr. Mann said, adding, “He

is the guy who put the Naked Angels on the street. You know, John Kennedy was

of great use to him, but he didn’t use John Kennedy-they were really close

friends. He was really respectful of Kennedy’s feelings; he didn’t trot him out

like a trophy. The whole board of directors was attributable to Jack Merrill.

He was the impresario. He built the damn thing.”

Mr. Merrill acted in 28 Naked Angels productions, often cast

as a tough guy. In 1997, he went to Hollywood

for the TV pilot season and had an agency meeting. “There’s like seven agents,

and heads of the department, and assistants sitting in the back-one of those

big, classic Hollywood meetings,” he said. “And they

tell me that I’m the next this and I’m the next that: ‘You’re the next Tommy

Lee Jones'; ‘Look at him, he’s got a little of the Bruce Willis thing going

on'; ‘Billy Bob’-whatever-and ‘We’re so glad you’re

here, we’re thrilled,’ blah blah blah. I’m just stunned; I’m thinking nothing

like that ever happened to me before in my life, I don’t even know what to say.

I walk out of the office, and this agent puts his arm around my shoulder and

says, ‘Now, listen-when you buy your house out here, I think that you would

probably be happiest somewhere above Sunset in the hills.’ And I said, ‘Really,

that’s great-can we just work on gas in the car?’ And he smiled.”

After eight weeks, nothing happened. “I don’t like Los

Angeles,” Mr. Merrill said. “It’s one of those places

you go out for two weeks and think, ‘Wow, this is great. This weather’s perfect

and there’s flowers ,’ you’re driving

around and everyone’s got a house and

there’s a lot of work and everything’s great. And then you go on auditions

where they want to put a rubber thing on your head and have you be some alien.”

The friend Mr. Merrill sees most often is Ms. Estess, who is

paralyzed from Lou Gehrig’s disease. He visits her four or five times a week.

They met at N.Y.U., and now he helps her with Project ALS, a nonprofit she

founded. CBS has made a movie of Ms. Estess’ life, The Jenifer Estess Story , with Laura San Giacomo playing her.

“I think he wants to

will me back to health, which is pretty cool,” said Ms. Estess. “He’s extremely

persevering, a wild force of nature or something-he just sort of propels

forward. I remember when we were at Naked Angels and thinking about getting our

first project up, and everybody was like, ‘Oh, we’re not ready; maybe we

shouldn’t do it,’ and Merrill’s like, ‘We’re doing it.’ He’s about getting it

up and getting it out. It’s about carpe

diem . In terms of the scene here, I think he’s a leader. Although right now

Merrill is not Mel Gibson, he does rally the troops forward; he definitely

rallies New

York City

in a great way, sort of keeps it moving.”

The one thing about straight life that Mr. Merrill says he

yearns for is a traditional marriage.

“There is something

about being gay and going to weddings and seeing families stand up and make

speeches about how happy they are about this union , and how thrilled  about the love that these people are experiencing. And you know,

I have been to them and thought, ‘That will never happen to me.’ I don’t get to

do that: I don’t get to have everybody come and tell me how proud and happy

they are that I have met somebody who I love and want to spend the rest of my

life with. I don’t get to do that. And if I do, it’s not real . I didn’t really get

married. It doesn’t really count.”

On a recent night,

documentary filmmaker Alexandra Shiva ( Bombay

Eunuch ), who is a board member of Urban Empire,  took Mr. Merrill to a $1,000-a-head

benefit for the Public Theater. There was a private barbecue dinner by the

Great Lawn in Central

Park, followed by a

performance of The Seagull at the

Delacorte Theater and then a party on top of Belvedere Castle. Mr. Merrill, wearing a fedora, mingled near cast members Christopher

Walken, Kevin Kline, Philip Seymour Hoffman and John Goodman; bummed a smoke

off actor Liev Schreiber; and fell into conversation with  Marcia Gay Harden, who won the Best

Supporting Actress Oscar this year for her role as Lee Krasner in Pollock . 

“Let me tell you something, you looked beautiful,” he told

her. “I was at the boob tube, root-toot-tooting. You looked so fucking

beautiful. I was like, ‘Oh my God, she’s a huge movie star. She’s a movie

star!'”

Ms. Harden said she was going for an Ava Gardner–Jackie O.

look.

“You want to know

something?” Mr. Merrill said. “You looked like a total fucking movie star. You

know, I love the girls with their hair all fucked up, and then you come out: a

red dress, fucking hair, it’s like, ‘You go,

Marcia Gay Harden! You get up there and you be that fucking movie star, Marcia Gay!”

At midnight, people sang happy birthday to Ms. Shiva. Mr.

Merrill escorted her down the castle’s stone steps, and they got into a golf

cart. They zipped past the people who were already camping out to buy tickets

for The Seagull . Ms. Shiva checked the messages on her cell phone. There

was a voice mail from Daniella Rich, who’d bought a ticket for the benefit but

discovered, when she arrived, that her name wasn’t on the list. So she went

home.

“Oh my God, it’s horrible-she’s pissed, ” Ms. Shiva said.

Mr. Merrill said he felt awful, too, but then he leaned over

conspiratorially and said, “It’s a great New York

night.”