This story originally appeared in the April 20 issue of The Hollywood Reporter.

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It was a quick elevator ride that occurred more than a decade ago in the Carlyle Hotel, New York’s old-world Art Deco bastion of elegance. During the mid-1990s, Dan Camp, then-president of the Upper East Side property, found himself in an elevator one evening with Princess Diana, a regular at the Carlyle. But things turned surreal when two other regulars boarded the lift: Steve Jobs and Michael Jackson. The three exchanged courtesies, and when the white-gloved elevator operator deposited the lift onto the ground floor, the riders went their separate ways. “This was the last thing in the world you would ever expect to happen,” says Camp, “but these kinds of things happened with some degree of regularity.”

The Carlyle, located a block from Central Park at 35 E. 76th St., long has been an A-list address for presidents, moguls and Hollywood icons alike. The 35-story tower, built in 1930 by developer Moses Ginsberg, stands apart because it includes a four-star hotel (188 rooms) and luxurious co-op residences (60). And the bevy of notables who have lived, stayed, dined and drunk there impart it with a mystique that is unmatched.

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To wit: President Kennedy stayed at the Carlyle before and during his time in the White House, and stories persist of his dalliances there with Marilyn Monroe (an FBI memo includes allegations of sex parties held at the hotel that included Monroe and Frank Sinatra). Vera Wang opened her first bridal salon at the Carlyle in 1990. And for more than a decade, Woody Allen has played clarinet at the property’s Cafe Carlyle, which was long home to famed cabaret singer Bobby Short. Allen considers the building a “cultural landmark,” telling THR in an email interview that the Carlyle “carries on a great Manhattan tradition. It’s the kind of place you go to meet for drinks the way people used to in old New York romantic movies.”

Residents include IAC chairman Barry Diller and Paramount Pictures chairman Brad Grey, who first stayed as a guest before buying a $15.5 million unit at the property in November. And despite the big-name residents, there’s a tight-knit community at the Carlyle. 

“It’s very friendly, it’s warm, it’s terrific,” says actress-singer Elaine Stritch (30 Rock), a longtime resident. “I love knowing people in the lobby. I just saw Jamie Lee Curtis last night; Barry Diller gives me a hug about once a week. That’s not hard to take.” And the hotel guests — past and present — are a who’s who of Hollywood: Steve McQueen, for example, used to stay there, and these days it’s frequented by the likes of George Clooney and Tom Cruise and Katie Holmes. 

But don’t expect anyone affiliated with the property to discuss any of this. And that’s part of the charm. “Every time I [look at] a daily review of our arrivals, it is unbelievable how many celebrities are going to that hotel — but you just don’t see them,” says Bob Boulogne, COO of Rosewood Hotels Resorts, which has managed the property since 2001, when it was purchased by Maritz Wolff Co. The St. Louis-based hotel investment group and part owner of Rosewood sold the Carlyle in July to the family of Hong Kong billionaire Cheng Yu-teng in a five-property, $570 million portfolio.

Observers expect the level of service — think: dog walkers, hand-delivered mail and personalized flower arrangements — to remain impressively high. Same goes for the prices. Rooms start at about $700 a night and top out at $15,000 for the Empire Suite, a three-bedroom duplex. And things remain as heady as ever on the residential side.

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Grey’s purchase of a four-bedroom unit that encompasses the tower’s entire 26th floor illustrates the premium the building often commands. The deal for the 3,000-square-foot apartment broke down to about $5,167 a square foot — roughly five times the price at which luxury condos in L.A. trade. But not every unit is so dear: A two-bedroom residence listed at $1.35 million recently sold, and in March, a two-bedroom, upper-floor unit was listed at $3.5 million. Properties that buyers cross shop include The Pierre and 15 Central Park West.

The monthly maintenance fees for residences at the Carlyle, which became a cooperative building in 1970, are staggering: Grey pays $37,946 a month. And a source with knowledge of the property says that fees start at about $7,500. “It’s all just great fun, and every three months they hit you with the bill, and it is terrifying,” says Stritch, who performs at Cafe Carlyle once a year. “That doesn’t get any laughs at all.”

The fees partly pay for exacting service from the staff of 420 employees. Residences are cleaned and turned down daily, and owners can order room service and use the spa. But the fees are high enough that they might scare off some prospective buyers, resulting in “relatively good values,” says Corcoran Group agent Patricia Cliff. “They are hard to sell because you are talking about a very, very restricted clientele.”

That clientele has left a trail of stories — some perhaps apocryphal. Private-equity firm Carlyle Group, which has ties to the Bush family and invests in defense and aerospace, got its name from the hotel after its founders met there during the 1980s to plot business plans. Others have used the Carlyle name, too: Ron Howard named his daughter Jocelyn Carlyle because she was conceived there. In 1995, Phil Spector allegedly pulled a gun on a photographer and tried to force her into his room, according to documents revealed in the music producer’s first murder trial for killing Lana Clarkson. And the final details of the Viacom-Paramount merger were hammered out there between Sumner Redstone and Martin Davis in 1993.

In June, a $350,000 Fernand Leger painting was stolen from the lobby. (The thief, Mark Lugo, was caught and in February sentenced to a stint in prison.) And in another legal matter, earlier this year, resident Murray Schwartz, former CEO of Merv Griffin Enterprises, sued the Carlyle over a water leak that caused more than $350,000 in damage to his home. He has alleged that workers stole valuables from his residence while repairing it, according to the New York Post. Carlyle management declined comment.

But some of the best stories speak to the odd assemblage of people who find their way to the Carlyle. Frank Bowling, a former vp at the Carlyle and now ambassador for the Montage Beverly Hills, says he recently spied French President Nicolas Sarkozy leaving for a jog followed by what looked liked “a soccer team.” But the hulking group was just his security detail. And over the years, lucky Bemelmans Bar imbibers have been treated to surprise performances by Tony Bennett, who occasionally will hop onstage when singer and friend Barbara Carroll has a gig.

Then there is the aforementioned Camp, now an art collector, who recalls an encounter in which he found himself introducing President Reagan to the King of Pop near the lobby’s bank of four elevators. “You could tell they were both standing there and wanted to meet each other and didn’t know how to go about it. It is a terribly eclectic group of people that stays there.”

Email: Daniel.Miller@THR.com

Twitter: @DanielNMiller