A thousand people raged until 4 a.m. at 80-year-old James Goldstein’s Halloween party last year. Two days later, the singular host — who straddles the spheres of entertainment, style, sports, art and architecture like no one else in Los Angeles — bumped into Leonardo DiCaprio at LACMA’s Art + Film Gala. 

“I said, ‘I wanted to invite you, but I didn’t have your number,’ ” Goldstein recalls. “He says, ‘I was there, wearing a mask.’ It turns out Jamie Foxx was there too, in some unrecognizable costume.” Conspicuously not in attendance was Goldstein’s Beverly Crest neighbor Sandra Bullock, whom he had invited. Based on the history of their relationship, Goldstein theorizes she may have been responsible for calling the cops with a noise complaint, though, “I can’t say with any proof.”

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Frizzy-haired and springy-stepped, in head-to-toe designer leather — or, when at home, brightly contrasting tennis gear — Goldstein is the poster octogenarian of a certain kind of man, one whom some find admirable and others repellent. A real-estate investor, he puts his net worth “in the ballpark” of $100 million. More consequential is what that fortune allows: the freedom to cultivate what once would’ve been referred to as insouciance, and is now, among the young and fashionable crowd he surrounds himself with, an IDGAF philosophy. Case in point, he spends most nights courtside at the Staples Center in his trademark peacocking attire, often with a date young enough to be his granddaughter.

It’s a weekday and, as he has since the ’70s in what may just be the city’s longest-running act of property-tinkering, he tends to his world-famous dwelling, the Sheats-Goldstein Residence, designed by heralded midcentury architect John Lautner and considered a modernist masterpiece (though most famous for its appearance in 1998’s The Big Lebowski). There are, as ever, contractors to hound and blueprints to review, especially as he seeks to finally complete an adjacent Lautner-esque entertaining complex he began about 15 years ago. To do so, Goldstein knocked down an actual Lautner that stood on the lot. Preservationists blanched. Goldstein says the architect, who died in 1994, gave him his blessing.

Built in phases, the top floor of the complex features a tennis court with an infinity edge. Below is a European-style discotheque he’s dubbed Club James. Its first bash was a surprise birthday he hosted for Rihanna in 2015. On the ground floor is a soon-to-be-completed ultra-narrow lap pool. “When I had this pool designed, the style wasn’t very common,” he sighs. “By the time I’m finished, all these $30 million spec houses had them.”

Goldstein, who paid $182,000 in 1972 for the main house, is vexed by what he perceives as the notion that he’s spent all these years merely engaged in the act of “restoration,” pointing out the original version, designed by the Sheats family, includes many effronteries of taste, like wall-to-wall green shag carpeting “almost comical it was so bad.” The final phase for the new complex will feature a theater to screen the NBA games he can’t attend and a guest house. “At my age, I’m concerned that I won’t be around long enough to complete them,” Goldstein says.

Meanwhile, the main house remains booked for shoots — mostly fashion and commercials — multiple days a week. (The cost varies wildly depending on the production.) He recently allowed the venue to host its first wedding ceremony but decided never again. “I don’t want this to be a chapel,” says the never-married, matrimony-averse Goldstein, who in the ’90s hosted adult film shoots on-site. “A party afterward, I’m open to that.”

The house long has been typecast as a den of iniquity, a fantasy hideout for rappers like Snoop Dogg and G-Eazy in their music videos or pornographer Jackie Treehorn in The Big Lebowski. “People are always coming over here dressed as characters from that movie,” says Goldstein, who’s fine with it being associated with cinema’s miscreants. In fact, he “doesn’t understand” why, 25 films in, the James Bond folks have yet to inquire about utilizing what, to him, is so quintessential a location for an evildoer’s lair. Goldstein himself — who despite his flashy exterior possesses a restrained personality, speaking in a low-key drone — is comfortable with being perceived as a villain, whether as a go-his-own-way architectural preservationist, a hometown-hating basketball fan, a litigious businessman or an elderly libertine.

“The villains always live in the modern houses, and the heroes live in the home with the white picket fence,” he says. “It is the way it is.”

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Goldstein spends up to eight months a year on the road, mostly attending NBA games — sometimes five a week, typically 100 a year. He spends $500,000 each season on seats. A sports nut since childhood, he once followed other leagues but realized he was “wasting my time” when, on the same day in 1988, he attended a Dodgers World Series game and a Lakers preseason contest and found himself far more compelled by the latter. Goldstein won’t disclose how much, but he’s contributed a sizable amount toward the renovation of the Basketball Hall of Fame in Massachusetts for the James F. Goldstein SuperFan Gallery to debut in June, featuring a permanent exhibit devoted to him along with materials cataloging other notable supporters of the game, including the late Penny Marshall.

Goldstein has developed a heel’s reputation for his devotional Lakers attendance without rooting for the Lakers. When he’s at Staples Center, he sits courtside next to the visitor’s bench. “I’ll leave it up to others to draw psychological conclusions, but no matter what game I go to, I root for the visitor,” he explains. “I don’t want to be part of what I call ‘the masses.’ Everybody is moving in one direction, and I’m going the other way.” He does allow that he’s galled by a sense of entitlement specific to Lakers fans: “There’s an arrogance: ‘We deserve LeBron.’ ‘We deserve Anthony Davis.’ ” (As it happens, the LeBron James-starring Space Jam 2, set for July 2021, was shot in part at Goldstein’s tennis court, converted into a basketball court for the occasion.)

His lack of hometown pride has led to estrangement among the courtside clique. While he’s on good terms with Jack Nicholson, he says, radio mogul Norm Pattiz “has a deep hatred toward me. Besides ignoring me in the VIP room, one time we were seated next to each other during the Finals, and he was leaning over so that I couldn’t see. I very timidly said to him, ‘Norm, can you please sit back so I can see?’ He said, ‘Fuck you.’ That’s how bad it is.”

Goldstein’s high-profile, long-standing non-Lakerdom kept his relationship with Kobe Bryant prickly, too. But when he learned, while traveling abroad, about Bryant’s death (“I must have gotten 30 text messages in five minutes”), it hit hard. “It wasn’t just that he died, but the way it happened: a stupid mistake,” he says. “It really, really got to me.”

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At a recent Lakers game, Oscar-nominated actress Dyan Cannon, a fellow courtside regular, gave Goldstein good-natured grief over one of his other well-known predilections — dating barely legal women. “I took a 19-year-old girl to the game who’s a model,” he says. “When Dyan walked by, she said to me, ‘Security is looking for you.’ I said, ‘Why?’ She said, ‘Because you’re with a girl who’s 13.’ ” (When he gives a model a tour of his house, he’ll have her step on a scale concealed under his bedroom’s floor so he can catch a look at her weight.)

Once, Goldstein took up with a notable older woman: Jayne Mansfield. As a 24-year-old grad student enrolled in UCLA’s business school in 1964, he met the actress, eight years his senior, at the Whiskey a Go Go in West Hollywood. They embarked on a “six-month romance” — despite her then-marriage to Mickey Hargitay, a Mr. Universe (and the father, with Mansfield, of Law & Order: SVU star Mariska Hargitay.) Goldstein persisted with the affair even after being attacked when Hargitay discovered the pair together. “He started bashing me over the head,” says Goldstein. “She was standing there screaming. I begged for my life.”

Goldstein attributes his interest in style to his father, the owner of a small department store who “got me going on clothes at a young age.” Still, “he was a very conservative dresser, so I quickly branched out from what he liked.” At 13, when others were wearing pink shirts, “I took it a step further and got a pink suit. I was always trying to be ahead of everyone else.”

Now Goldstein, who attends dozens of fashion shows each year, dresses in a leather-heavy mix of Gaultier, Cavalli, Galliano and Balmain. Saint Laurent designer Hedi Slimane sees him as a muse. Colette, the former Parisian concept boutique, once sold T-shirts with his face on them.

His aesthetic has been described in the media as “couture cowboy,” a label he chafes at. “A cowboy hat, the brim is turned up,” he says, “A pimp hat, the brim is turned down.” Besides, “there’s nothing American West about having the hats made in python.”

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Goldstein is game to hold forth for hours about his glittery passions. Yet he shuts down when asked about the work that funds them. “You’re getting into an area that I don’t want to talk about,” he says.

As such, most media accounts have described him as a mystery man. “I like it,” he acknowledges. He sees his “income-producing work,” which he claims only requires “maybe a couple hours a week,” as an incidental part of his life — “a means to generate what I really love to do.” He says his net worth could be far larger by now if that were his prime focus.

Goldstein, who studied mathematics and physics at Stanford before receiving his MBA from UCLA, is in fact a California mobile home park kingpin who’s made his fortune packaging groups of properties into investment vehicles and then suing municipalities, like Palm Springs and Palm Desert, if they thwart his attempts to end rent control. Most cities settle. But his persistent legal efforts against the city of Carson, near LAX, led to a landmark 2015 State Supreme Court decision against him.

“His castle was built on the backs of the most vulnerable people in society,” says Sunny Soltani, Carson’s city attorney, who estimates that about 2,000 residents have been affected by his efforts. By her records, Goldstein’s unsuccessful campaign of “litigation terrorism” against Carson has cost it $3 million in legal fees since 2005.

To Goldstein’s mind, he’s just another American in noble conflict with City Hall. “I felt that things were happening that were unjust, that cities were taking advantage of me,” he says. “So I wanted to fight against them, no matter what it cost or how long it took.”

For a time, Goldstein — who grew up in Racine, Wisconsin (the area’s Frank Lloyd Wright homes sparked his love of architecture), and has no heirs — intended to gift his estate after his death to the National Historic Trust. But he was left cold by its modernism-indifferent new head and found a fresh suitor in LACMA director Michael Govan. According to Govan, their deal is meant not just to preserve the property but for it to remain active and relevant. “It’s about keeping it alive so it doesn’t get dusty,” he says. “Keep the shoots going, the events. It never has to be a historical house. It can always be a future-looking thing.” Goldstein, who estimates the estate is now worth $75 million, had to donate an additional $17 million to LACMA as an endowment fund for maintenance.

John McIlwee, a business manager who restored his own Lautner residence in the Hollywood Hills, believes Goldstein deserves credit for keeping the property open to the public, whether for all-night parties or docent-led walking tours. “There are others who buy a home and keep it to themselves, closing it off,” he says, “and the world loses something.”

Other owners of Lautner showpieces marvel at Goldstein’s tolerance for never-ending domestic upheaval. (He recalls with an understated shrug the multiple years spent “basically living outside” during one stretch of renovation when all of the glass had been removed from the living room.) “That Goldstein model would put me in a mental home,” says writer-producer Mitch Glazer, who renovated his own Hollywood Hills Lautner in the ’90s. “I couldn’t wait to get those [construction] guys out and watch football.”

In Goldstein’s entertainment complex, just off Club James, there’s a library alcove that serves as the VIP room during parties. It features a curated selection of his press and photo shoots. “I’ve never had a PR person,” he says. “The word just gets around.” Here, Goldstein considers the idea of being buried on-site in yet another structure, a small mausoleum. “I thought that if it were legal,” he ponders, after a moment of silence, “it would be something that would be nice to have happen.” Then he strides past his discotheque, taking another appreciative glance at what he’s constructed, his arms sweeping out at the estate of glass and concrete. “This,” Goldstein says, “is built to last forever.”

This story first appeared in the March 11 issue of The Hollywood Reporter magazine. Click here to subscribe.