As he crosses broadway at 76th street, a man -- two stories up, a block away -- shrieks, "Hey, Macaulay!" out his window. Culkin gives a little wave and heads into the Amsterdam Billiard Club, where he likes to hang out. For one thing, he can smoke his Parliaments here, and for another, the patrons at this time of day are serious pool players who don't care much about the young man in their midst wearing blue jeans and a wine-colored leather jacket studded with rhinestones and grommets in the shapes of shooting stars and comets. "My stylist sent it over," he says with a self-mocking eye roll.
The bartender recognizes Culkin immediately. "I'll get that," he says, handing over a bottle of Poland Spring before the celebrity can go for his wallet. Culkin thanks him and settles himself on a high stool by the window. "It's funny," he says, flipping his bottle of free water in his hands. "The more money you have, the less you need." When he got his first credit card, Culkin bought a $600 ebony cane with a sterling-silver tip, "because I could." He laughs, pushes his hands through his blond hair, and lights a cigarette. "I feel like some rich little kid left me his inheritance." He looks older in this light; leaning on one knee, smoking in his leather with his hair back and the sound of pool balls snapping all around him. "No," he says, exhaling smoke. "I feel like some little kid worked really, really hard and I got his money."
It was when Culkin's mother filed a custody suit that he found out just how much he was worth: some $50 million. "My father would hide newspapers from me so I wouldn't read the stuff about him or find out how much I was making. I can understand why they did that; they didn't want me running off to my friends saying, 'I just made $8 million!' "
But as the custody case moved through the courts, Culkin, then 16, decided to gain control of his finances. "He didn't want to be the subject of his parents' dispute," says Weinrib.
"Basically, I had millions and millions of dollars in the bank and my mother couldn't pay the rent because she was spending all of her money on lawyers," Culkin says. "We were about to get evicted from our apartment. The only way I could get access to that money was to take my father's name off it, but I didn't want to make it messy, so I figured I'd take both their names off.
"That's kind of something that's up in the air in my brain," he continues, "whether parents should be earning money from their children in that kind of way. That's something for future generations of child actors to figure out, whether parents should be creating that dynamic."
Kit Culkin never showed up for the last day of the trial, and his son has not seen or spoken to him since. There is still a bench warrant out for Kit's arrest for allegedly assaulting a photographer at the trial. "When he disappeared after the trial," says Culkin, "first he stole all my memorabilia, like my very first costume and all the things I had collected over the years. My pictures, this and that. Stuff that I was going to put in storage and dig out when I was 50 or 60 for a laugh. He took that with him."
Ken Weinrib thinks that once Kit lost control of his child's finances, it dawned on him that he would lose control of his children altogether. "I wasn't surprised when he didn't show up for the last day," Weinrib says. "I don't think anyone who knew him was. He wasn't after Mack's money -- none of it was ever really about money -- but that decision made it apparent that he wasn't gonna get control of everything. He was gonna lose."
"For now, my opinion is, the farther away he is the better when it comes to, like, everything," Culkin says. "We think he's in Arizona. That guy always wanted to be a cowboy."
"High school was a great time," Culkin says brightly. "When Kit left, it was like, I can finally have my own room, you know what I'm saying?" He attended the Professional Children's School and had a group of twenty friends who would hang out in his room every day. His apartment became their headquarters. "People would come from all over the city and put their names up there: I had floor-to-ceiling, wall-to-wall graffiti. Even the tiles on my bathroom, on my toilet, on my mirrors, on the ceiling. Everywhere. It was something I always wanted to do, and now that he was gone I could."
They were a pack of "pseudo-punks," Culkin says, loitering around Sim's deli on Columbus Avenue, where they went for smokes, stealing orange caution cones from the street and vandalizing the occasional parking meter. "I did all those kind of great things, like I dyed my hair. I did purple and I did pink and I did orange, and they made such a big deal out of it -- it was on the cover of People!"
"They were always printing things about his beer parties," says a former classmate, "but he was as normal as you could be if you were fucking superfamous and a millionaire at 8."
"His way of rebelling was not to fulfill everyone's expectations and become little Mr. Hot Shit and go to Moomba to bring home six models every night and do drugs," says Gregory Mosher.
"It was so blown out of proportion," Culkin says. "I never did anything more than any upper-class Upper West Side kid you know would. We weren't, like, all squatting in the corner shooting heroin."
By his senior year, though, Culkin was attending school "for purely social reasons. It was one of those things where I could pass without lifting a finger," he says. "That was kind of pissing them off. I'd get really high scores on my standardized tests but like D's across the board." And then there was the matter of the stool he brought with him from class to class, refusing to sit on one of the school's regular chairs. "Eventually, they called me in and said, 'We think you're trying to tell us something with that stool.' " Ultimately, he dropped out, a few credits shy of graduation.
He met his wife, Rachel Miner, when he was 14. "She always says she thought I was a jerk," Culkin says. "On the first day of school, she said, 'Hi, my name is Rachel,' and I said, 'Yeah, welcome to the school,' or whatever. She thought I was such a jerk for not saying, 'And my name is Mack.' "
When he talks about Miner, he is talking on the one hand about a marriage, on the other about going steady. "We hung out in a big group of people, and you start kind of pairing off. We dated four times before we got married. She'd broken up with me three times before, and so the last time we were going out I said, 'Marry me now before you dump me again.'
"What can I say?" he says now, sounding a bit wistful. "She was my girl."