Life with My Sister Madonna (11 page)

In September, I go back to Manhattan and—because I am still painting and interested in art—get a receptionist job at the Diane Brown Gallery in SoHo.

Madonna invites me to see her perform at the first annual
MTV Video Music Awards
at Radio City on September 14, 1984. She has been nominated for Best New Artist Video for “Border-line” and is also performing at the show.

I meet her at Maripol's loft. Maripol is styling and dressing her up as a kind of punk bride. When I arrive, she is fastening rubber bracelets to Madonna's wrists, helping her into white tights, a tight white bustier and skirt, and clasping her
BOY TOY
belt round her waist. I take one look at the result and—though I don't voice the sentiment—think she looks ridiculous but I know her fans will love the look.

Way in one corner of the loft, a woman with black hair and a leather cap covering her face is sitting on the floor, watching intently as my sister is getting dressed. The woman doesn't say a word, but just gazes at Madonna, transfixed. Finally, after Madonna's outfit is accessorized with a crucifix and a white tulle veil, the woman takes her eyes off Madonna and glances in my direction.

“Cher, meet my brother Christopher,” Madonna says.

I smile and, for the first time, take a good look at the woman. It really is Cher. She seems lonely, and I think it strange that she is just sitting there staring at Madonna while she is getting dressed. I haven't got a clue why she's in the room, or how she and Madonna met, and whether or not they are friends, but Madonna is far too busy preparing for her upcoming performance for me to ask.

However, this moment marks the second of the intriguing encounters I have with celebrities I meet through my sister, or simply because I'm Madonna's brother. Basquiat is the first. Cher, the second. The rest, in no particular order, will include Demi Moore, Courtney Love, Lisa Marie Presley, Bruce Willis, Donatella Versace, Kate Moss, Dolly Parton, Johnny Depp, Liza Minnelli, the Spice Girls, Farrah Fawcett, Naomi Campbell, Jack Nicholson, Luciano Pavarotti, Denzel Washington, Mark Wahlberg, Warren Beatty, Sean Penn, Sting, Trudie Styler, Gwyneth Paltrow, and more.

Through all my encounters with celebrities I feel privileged to have access to so many people whom I admire. Often, I meet stars because I am Madonna's date at an event, but she rarely gives any of them more than a cursory glance. Most of the time, she is really bored and wants to leave as quickly as possible. And she is hardly ever impressed by meeting other famous people, so when we do, I make a point of keeping in contact with them on her behalf and because I want to.

That night at the MTV awards, my sister is the star, and after Bette Midler cattily introduces her as “the woman who pulled herself up by her bra straps,” Madonna upstages Bette resoundingly.

The audience may be enthralled by Madonna, but I watch the greenroom TV, see her pop out of a wedding cake, and squirm. As she rolls around the stage, the thought flashes across my mind as to what our father and Grandma Elsie must both be thinking as they see her act on TV. I wonder if my sister is at all troubled at the possibility of shocking or hurting them, but remembering her teen talent show, I doubt it. Nor will I ask her. Since the “Lucky Star” video, we have had little contact, and this evening is not exactly the right moment in which to start. Apart from working ceaselessly to become an even bigger star, she is about to fall in love deeply and, some say, for always.

On the L.A. set of the “Material Girl” video, as Madonna is sashaying down a staircase, decked out in a fuchsia satin replica of the Travilla gown Marilyn wore in
Gentlemen Prefer Blondes,
she comes face-to-face with hot actor Sean Penn.

He is twenty-four, she is twenty-six, their birthdays are just one day apart, and—for both of them—it is love at first sight. Afterward, she will claim that Sean reminds her of pictures she's seen of our father when he was young.

After the video shoot, Sean goes to a friend's house. The friend is reading from a book of quotations, turns to a page, and reads out the following random quote: “She had the innocence of a child and the wit of a man.” As Sean later remembered it, “I looked at my friend and he just said, ‘Go get her.' So I did.”

On February 13, 1985, she and Sean go on their first date together. After that, for both of them, there is no question that they want to be together, for now and always.

 

T
HE
Like a Virgin
album sells 3.5 million copies in just twelve weeks, is the first solo album by a female artist ever to be certified for sales of 5 million copies, and knocks Bruce Springsteen off the top of the charts and stays there. And not long after, “Crazy for You” will become America's number one single, as well. My sister is now a pop phenomenon. I think back to our games of Monopoly and conclude that she could now probably afford to buy Park Place for real.

Meanwhile, I am enjoying my job at the art gallery and am happy with my life in Manhattan with Danny.

That is, until my sister comes calling again.

“Come out to L.A., Chris. Come work, be my assistant. It'll be so cool. I'm going out on tour soon, and you can be my dresser.”

Her dresser? “Why not dancer, Madonna?” I say, somewhat flummoxed.

“I can get a thousand dancers, but only one brother to dress me.” Well, I may be gay, but taking on the role of dresser seems a step too far, and I tell her so.

“But, Chris, I don't want any fucking stranger seeing me naked. You're my brother. You're the only person I trust. I need you.”

My big sister needs me.

The next morning, much to my boyfriend's dismay, I fly to L.A.

T
WO MONTHS BEFORE
the
Like a Virgin
tour begins, I move out to Los Angeles and stay with Madonna and Sean at his home on Carbon Mesa Road, Malibu—a single-level, white stucco Spanish hacienda with a tile roof, built in a dry, arid canyon.

The first thing I notice is that the entire property, small as it is, is fenced in by a big wall topped by metal spikes. As I approach the house via a center courtyard with a disused fountain in the middle. I see that the front door is open and walk in. The living room is furnished with clunky, hand-painted and hand-carved Mexican furniture. Nothing fancy, no particular style at all. Typical of the owner of the house, Sean Penn, my future brother-in-law, who is not into home interiors and wants you to know it. Madonna is at a meeting in Burbank, but Sean sets about making me feel comfortable.

First, a firm handshake. Definite, manly. Different from that of Madonna's second husband, Guy Ritchie, whose handshake is a trifle unsure. Apart from that, husband number one and husband number two have one marked similarity—Guy and Sean are both middle-class boys from comfortable homes and yet are prone to present themselves as tough street kids. My sister, I believe, has always played the identical game. After all, she is a middle-class girl who propagates the myth that she landed in Times Square with just a pair of ballet shoes and $35. Perhaps this partially explains Madonna's attraction to both Sean and Guy. That and a mutual love of guns.

But unlike Guy in the future, Sean does his best to make me feel comfortable, to be brotherly. A beer? A pizza? A shot of tequila? I opt for the tequila, wanting then, and always, to be more one of the guys than I am. Not that Sean is homophobic. Or if he is, as an accomplished actor he disguises it masterfully.

 

H
E SPENDS A
great deal of time away from the house, and so does Madonna, so I am often left to my own resources. I'm not particularly comfortable at the house, where my room is Spartan in the extreme, with just a bed, a table lamp, no artwork, no drapes. Madonna doesn't seem particularly at home in the house either. She tells me that she feels isolated, and I don't blame her. She's a city girl, and being stuck out in Malibu—however beautiful the place may be—feels strange to her.

Sometimes we watch movies together, but rarely with Sean, who is usually off somewhere filming. If he is home, he and Madonna never have guests over to the house. From the first, I get the distinct impression that Sean is reclusive and feels happiest hiding out at home with Madonna alone. I stay out of their way as much as I can, except that now and again I cook dinner for her and Sean.

One night, soon after I arrive at the house, I roast a couple of chickens for us all. Halfway through the meal, Sean leans over to Madonna and takes a piece of chicken from her plate.

“Just stop that, Sean,” she says, and slaps his hand.

Sean grins at her and takes another piece.

I am starting to deconstruct my sister's attraction to Sean. He is a dead ringer for our father as a young man, is middle-class like Madonna but with a street-kid persona, and presents himself as a bad boy and is a rebel—just like our brothers. Patently a recipe for disaster.

 

M
Y JOB AS
Madonna's assistant is varied and far more interesting than working at Fiorucci. I return calls for her, keep her diary, make her appointments—some of which are with mogul David Geffen, who continually proposes that my sister marry him, whereupon she always refuses.

One of my regular tasks is feeding Hank. Half-Akita, half-wolf, Hank is a gift to Sean from Madonna. When I first arrive at the house, I am confident that feeding him will be easy. I've only heard his bark and haven't yet seen him. But I'm curious why he is always outside the house, in a fenced-off area behind a gate.

Sean quickly enlightens me.

He hands me a heavy black leather suit, a big coat and big gloves, along with a warning: unless I run to the gate and quickly slip Hank's bowl of raw meat through a crack, he'll probably bite me.

Bite me? I take one look at Hank, hurtling toward me like the hound of the Baskervilles on speed, and know that he'll definitely kill me. Easily, and with one chomp. He is massive. Fearsome. A wild animal, not remotely domesticated. But Sean adores him. And he makes no secret of just loving it that Hank scares the shit out of everyone who comes within a mile of him. If he didn't, Hank would long since have been put down.

Sean also loves his friend the writer Charles Bukowski, who lumbers into the house, day or night, blind drunk and puking. The moment he arrives, my sister escapes into the bedroom, disgusted. Strangely enough, Madonna and Bukowski are born on the same date—different years—and she usually admires good writers, but she loathes few things more than an undisciplined drunk. Or a gun collector. Perhaps she, too, has never forgotten Marty and Anthony menacing us with BB guns when we were kids.

As the son of director Leo Penn and his wife, actress Eileen Ryan, Sean is minor Hollywood royalty. Years later, he will reveal that both his parents drank heavily once the children were in bed at night, but never showed any evidence of drunkenness in the morning. In retrospect, I conclude that perhaps with Bukowski, who was almost forty years his senior, Sean was reliving some of the dynamics of his relationship with his father.

 

U
NFORTUNATELY FOR
S
EAN,
he is about to be confronted with a new and unfamiliar fact of life; since meeting Madonna just a few months before, her career has already made a quantum leap and her fame has increased by almost epic proportions. Madonna has been profiled in
Newsweek,
the single “Material Girl” has hit the U.S. charts at number two, and after
Desperately Seeking Susan
is released on March 29 and Madonna receives great acclaim for her performance—which I still can't help thinking is Madonna just being herself—her star is even further in the ascendant.

 

M
Y JOB AS
dresser for
The Virgin Tour
begins. We rehearse for three weeks in L.A., and I get basic on-the-job training on how to be Madonna's dresser.

On the road, when we stay at hotels, my day begins when, first thing in the morning, I go to my sister's room, check her messages, order sourdough toast and coffee for her, and return her calls. Then I and the rest of the team—including her dancers and the band—go to either the current venue or the next. Madonna always travels first class. She is careful not to show favoritism toward me because I'm her brother. An irony, really, considering that she grew up our father's favorite and didn't protest, but perhaps she now believes that what was glorious for the goose is no longer fitting for the gander. So I fly coach with everyone else.

I arrive at the venue an hour before the show starts. In the dressing room, which on this tour is always in a small tent behind the stage, I inspect all the costumes and make sure that they are all on hand and in perfect condition. If an article of clothing has a hole in it or a hook missing, I quickly sew it up. As Madonna is extremely active onstage and always perspires a great deal, we tour with three versions of every outfit she wears onstage.

Hence we have fifteen pairs of fishnets, ten pairs of gloves, three painted jackets, and three versions of all the other costumes in the show. I make sure that her first outfit is laid out and waiting for her.

Blue lace bra, jean jacket, blue lace top, lace gloves, blue socks, leggings, blue jean skirt. Blue rag in her hair. Silver cross earring for her right ear, silver hearts earrings for her left, chain belt round her midriff. Two crosses around her neck, plus a gilt chain. Blue ankle boots.

I dress her before the show. When she is ready, she has her makeup done, and finally her hair. She will open the show with three songs. She sings the first two, “Dress You Up” and “Holiday,” wearing the jean jacket. Then she'll peel it off to do the last one, “Everybody,” in the lace top underneath. The rest of the outfit stays the same.

She will have a change of costume every two or three songs, and that change has to be completed in a minute and a half or less. To ensure that the changes happen like clockwork, I hang all the rest of her outfits on the clothes rack in the order she will wear them. I lay her shoes out on the floor and unroll the gloves she'll be wearing in the first change with the fingers folded back and turned inside out so she can just stick her hand through them quickly.

On April 10, 1985, opening night of
The Virgin Tour
with the first of three sold-out concerts at the Paramount Theater, Seattle, Washington, I'm probably even more nervous than my sister. We've rehearsed the timing of the changes over and over, but nothing can compare with the real thing—knowing that Madonna is about to come offstage and that I have to change her entire outfit in seconds.

After “Everybody,” she hurtles backstage.

She is wet with sweat and is breathing heavily.

I wipe her down.

She stands still while I remove all her jewelry, then her top, her skirt, the rag out of her hair.

She pauses to take a swig of Evian, and because every second counts, I use the time to check that all the fringes in her next outfit are unknotted.

Then I help her into it: the black bra top, black fringed waistcoat and skirt, and finally the long black gloves.

“What the fuck, Christopher, you haven't pushed out the little finger! Fuck you, you piece of shit,” she storms.

I stop dead, horrified.

“Hurry the fuck up, or I'll fucking fire you right now,” she screams.

I open my mouth, then close it.

She's due back onstage again in fifty seconds.

I straighten the fringe of her skirt again.

She stamps her foot, wriggles, and one of the hooks holding her bra snaps off.

Rather than take the time to sew up her bra with a needle and thread, I grab a safety pin and pin her bra together—careful not to let her know I'm using one.

“Fuck you, Christopher, I can't fucking believe how slow you are,” she screams.

Then she's back onstage, singing and dancing like there's no tomorrow.

While I am left in the tent, close to tears, thinking,
I can't do this job. I'm doing my best but all I get is screaming. I can't do this.

I hear the applause of the crowd, the cheering, and know that she'll soon be backstage again, screaming and shouting at me. I feel like walking out of the theater and never coming back.

Then I switch from dresser mode to brother mode and realize I can't abandon my sister. I think of the crowds, the fame, and the pressure on Madonna. Thousands of people are out there watching her, the adrenaline is pumping, she's thinking of a hundred different things. Fifteen songs, fifteen dance routines, lyrics, steps, voice, movement, hair, makeup. And how everything—plus the ticket sales, the crew's salary, the audience getting their money's worth—depends on her.

And at that moment, I realize that Madonna really wasn't lying when she said she needed me, because she genuinely does. I am the one person she can rely on, the one person at whom—when the pressure becomes unbearable–she can vent, and the one person who will take it, because I'm her brother, and I feel for her.

I make up my mind there and then that I'll endure the abuse, endure the pressure, and that I won't walk out, because ultimately, in the midst of the show, in the heat of the moment, my sister is at her most vulnerable and I want to be there for her because I empathize. Besides, she's including me in her crazy, fabulous world, and I am relishing every moment.

Some of those positive emotions evaporate when Madonna storms offstage, screaming at me again because her bra's come undone. She rips it off, sees the safety pin, and goes ballistic.

I listen to the torrent of swearwords and, instead of shrinking, flash back to our father scrubbing our tongues with soap because we'd said one solitary F-word. Nowadays, he'd need a whole crateful of soap to scrub Madonna's tongue.

I laugh silently to myself and carry on dressing her. After that, during each show, I block out all the obscenities, all the ranting, and concentrate instead on the change, focus on the job at hand, and ignore whatever she is yelling, unless it has to do with the costumes. Other than that, I learn to make myself scarce and not to react, no matter what.

In a way, this tour is a learning experience for both of us. She has never been on tour before, and I have never been a dresser. That she asked me, who has no experience, to dress her on her first tour is a testament to the trust she now has in me.

I believe that even a dresser with experience would still have found dressing Madonna difficult on
The Virgin Tour.
Other dressers had worked with stars before, but at this point few stars had toured with shows having so many costume changes. And I doubt that the majority sweat so much.

Wiping sweat off Madonna's body—even, at times, off her breasts—makes me incredibly uncomfortable. Nonetheless, during each and every change, I do just that because she needs me, and because that's part of my job.