Long before TikTok and Instagram, indeed for much of the 20th century, newspaper gossip and society columns regularly announced who had spent extravagantly and who had behaved badly. It was a time when interest in high society matched, or even surpassed, interest in Hollywood actors and Broadway starlets, and Prince Serge Obolensky, a nightlife-and-hospitality impresario, who seemed to know everyone and be everywhere, could always be found among the boldface names.
Born into an aristocratic Russian family, the Oxford-educated, polo-playing prince fought in the Russian cavalry during World War I, then against the Bolsheviks during the Russian Revolution. His marriage to Princess Catherine Yurievskaya, daughter of Czar Alexander II, ended in divorce. His second wife, Ava Alice Astor, the daughter of John Jacob Astor IV, launched him into a different kind of aristocracy.
It was his brother-in-law Vincent Astor who installed him in the family’s vast American real-estate business, and in the depths of the Great Depression, Obolensky developed the strategy that would see him forever mentioned in the gossip columns. Tasked with renting out Astor-owned brownstones on two blocks at 86th Street and East End Avenue—which he privately nicknamed “Poverty Row” and “Busted Row”—he spruced up the properties with brightly painted doors, flower boxes, and colorful poles for clotheslines. Then he began throwing stylish parties, which helped fill the apartments with the young, smart set who had found themselves in reduced circumstances. Parties proved his talent.
The marriage into the Astor clan lasted nearly a decade and ended without apparent rancor or loss of employment. When the St. Regis hotel landed back under Astor control, in 1935, Obolensky was put in charge of its remodeling and relaunch, and it was here that Obolensky’s knack for creating fashionable scenes blossomed.
With the assistance of society doyenne Cameron Tiffany, new dining and dancing venues were created, including a Viennese-inspired roof garden, and Maisonette Russe, based on a popular Parisian night spot. The Iridium Room featured a retractable ice rink for skating exhibitions and revues. Obolensky imported Fernand “Pete” Petiot from the New York Bar (later Harry’s New York Bar), in Paris, to train the bartenders. It was Petiot who, it was said, introduced the Bloody Mary to the United States, although it was temporarily renamed the Red Snapper so as not to offend the hotel’s more sensitive guests.
Standing a formidable six feet two, speaking in a plummy Oxbridge accent, and with an aristocratic title to boot, Obolensky was the perfect front-of-house figure, often accompanied by Woogie, his piano-playing corgi, and the hotel flourished as a hub of sophisticated fun. (Somewhat more discreetly, it was at the St. Regis that Obolensky carried on a sporadic affair with the young Vogue fashion editor Barbara Cushing, long before she became the Truman Capote “swan” Babe Paley.)
A foray into the perfume-and-cosmetics business in 1937 featured a Fifth Avenue showroom decorated in the imperial-Russian style. The flagship fragrance, H.R.H., was “dedicated to Her Royal Highness, Duchess of Kent,” a longtime Obolensky friend. Given his flair for promotion, the luxury-cosmetics line might have succeeded had France not fallen to Germany, in 1940, cutting off supplies.
Obolensky was the perfect front-of-house figure, often accompanied by Woogie, his piano-playing corgi.
That same year, Obolensky attempted to enlist in the U.S. Army but was rejected because of his age—he was 49. Then, in 1942, with the United States at war, he approached a frequent St. Regis guest, William “Wild Bill” Donovan, who headed up the Office of Strategic Services (O.S.S.), the forerunner of the C.I.A. (The St. Regis was a hotbed of spying during the war. Ian Fleming favored it, and, unsurprisingly, so did James Bond.) The O.S.S., which some said stood for “Oh So Social” due to a surfeit of blue bloods among its ranks, agreed to recruit him, and not just for his refinement: Obolensky had experience in guerrilla warfare from his time fighting the Bolsheviks.
Fittingly, he was assigned to the Congressional Country Club, in Bethesda, Maryland. O.S.S. recruits arrived at the luxury property in blacked-out buses for rigorous training in hand-to-hand combat, live-fire exercises, and sabotage. At 53, Obolensky became the oldest recruit to complete paratrooper training in World War II, though it came at a price. After multiple parachute jumps in a single day, and with his legs taped together to relieve the pain from the hard landings, he is said to have ordered himself thrown out of the aircraft to complete his last jump requirement.
By 1943, he was in the field. One notable mission, code-named Operation Spleen, saw him parachute into Sardinia to deliver a proposal of cooperation from General Eisenhower to the local authorities following the fall of Mussolini’s regime. Commander Count Greppi, who led the Italian forces on the island, was more than amenable to joining the Allies, particularly after Obolensky dropped the name of Greppi’s uncle, who had served as Italian Ambassador in St. Petersburg.
Obolensky emerged in postwar gossip columns as “Col. Obolensky” and soon returned to the hotel business. Acting as manager and front man at the Plaza hotel, now under the control of Conrad Hilton, he opened a supper club—a mixed dining-and-dancing venue—called the Rendez-Vous. He enticed the photographer Cecil Beaton to design one of the hotel’s suites, which also functioned as an ad hoc photo studio. It was there that Beaton’s celebrated photos of Greta Garbo were snapped, and where an unlikely affair began between the photographer and the reclusive film star.
Obolensky always had an eye for the topical. When he took his talents to the Sherry-Netherland, he promoted it as the only hotel with a fallout shelter stocked with Geiger counters, medical facilities, and staff trained to handle the eventualities of nuclear war. A move to the Ambassador Hotel saw Beaton called in once again, and it was there that he photographed Marilyn Monroe in 1956.
The supper clubs Obolensky created—the Embassy Club at the Ambassador Hotel, Mon Plaisir at the Drake, Maisonette Russe at the St. Regis, and the Plaza’s Rendez-Vous—were his stages. He embraced the role of soigné host, and on Russian New Year’s Day, he’d climb atop a table, knives clenched between his teeth, to perform an exuberant Russian dagger dance, throwing the knives at $100 bills scattered on the floor.
Everything he did seemed to turn into column inches. In 1961, at the age of 71, he and the fading film star Merle Oberon were reported to have briefly stopped by the Peppermint Lounge, a seedy, Mob-owned nightclub on West 45th Street popular with rent boys and other Times Square denizens. The next day a small item appeared in the Cholly Knickerbocker gossip column, mentioning that Obolensky and Oberon had danced the Twist.
On Russian New Year’s Day, he’d climb atop a table, knives clenched in his teeth, to perform an exuberant Russian dagger dance.
Other columnists picked up on the story. The Twist, introduced by Chubby Checker the year before, had fallen out of fashion among teenagers but now underwent an explosive rebirth among the carriage trade as the Peppermint Twist, to the sounds of the club’s house band, Joey Dee & the Starliters. The great and the good descended on the dive bar, including Truman Capote, Greta Garbo, the Beatles, Norman Mailer, Judy Garland, and Jayne Mansfield, as well as the son of Turkey’s ambassador to the United States, music-industry newcomer Ahmet Ertegun. Never one to let a trend go to waste, Obolensky launched Twist parties at the Drake.
Inevitably, Obolensky began to slow, but to celebrate his 80th birthday, he threw a Winter Palace–themed costume gala at the Plaza. Some 400 guests were greeted by Obolensky in full Cossack uniform. It was a decidedly older crowd, and many of the boldface names he once knew had made their last appearance in the obituary pages.
He married for a third time, in 1971, to the 44-year-old Marilyn Fraser Wall, a Midwestern heiress. His death, at the age of 88, in 1978, seemed to signal the end of a nightlife era. Studio 54 had opened its doors the previous year, and a new type of V.I.P. was quickly displacing high-society personages in the gossip pages. Nevertheless, a case could be made that Obolensky was an influencer long before the term was coined.
Henry R. Schlesinger is a journalist and author who has written about espionage history for more than 20 years. His most recent book is Honey Trapped: Sex, Betrayal and Weaponized Love