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Authors: Andy Bull

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Let's start with what we know for sure. Clifford Gray was born in Chicago
in 1892, the son of an English father and an American mother. He is supposed to have attended Cornell, where he was a member of the Psi Upsilon fraternity—at least that was how his teammate Geoff Mason remembered him; Cornell has no record of Gray ever having attended. By 1910 he was in New York, writing subtitles for silent movies made by Jesse Lasky's Feature Play Company. From there he made the leap into starring on-screen himself. He had a series of roles in short films and made his debut in a full feature in 1915. The film was called
Beulah
, “a slapdash drama,” as one critic called it, which was unsurprising given the rate at which Hollywood rattled out its silent movies. Gray was in nine productions in 1916 alone. In 1917 he landed his first leading role, in
The Inspirations of Harry Larrabee
, “a breezy detective story” about a playwright caught up in a murder mystery. He followed that with
Alien Blood
, in which he shared the top of the bill. The best of the bunch of films Gray made was
Coney Island Princess
, in which he starred with Irene Fenwick (who, of course, went on to marry Jay O'Brien) and Owen Moore.

Moore remained a friend of Gray's for the rest of his life. Damon Runyon remembered hanging out with the two of them at a party in New York in 1933. Gray was passing through the city, having just returned from Paris. He had traveled back on the liner
Europa
, accompanying home the body of his fellow actor Jack Pickford. Gray, Pickford, and Moore all came up in Hollywood at the same time, a tight little circle of friends together through the 1910s. Moore had been married to Pickford's more celebrated sister, Mary, though they had long since separated. Gray didn't enjoy anything like the success of his two friends, though Moore tried to help him along, getting him work on a couple of bigger productions made by Myron Selznick's new studio. Moore and Pickford both earned their stars on the Hollywood walk of fame; Gray never came close to that. But in the long run he was luckier than either of his two friends, or perhaps just blessed with a stronger constitution. Moore was a lifelong alcoholic; Pickford was a notorious playboy who died at the age of thirty-six from neuritis brought on, rumors had it, by syphilis. They were the original Hollywood hell-raisers, as debauched and dissolute as any of the many who have followed in their footsteps.

In 1920 Gray and Moore were in Europe with Pickford and his wife, Olive Thomas. She had been one of Ziegfeld's girls from the Follies until she was signed by Selznick to star in his film
The Flapper
. “Two innocent-looking children, they were the gayest, wildest brats who ever stirred stardust on Broadway,” wrote their friend Frances Marion, who worked with Gray when he starred in the film
The Heart of a Hero
. “Both were talented, but they were much more
interested in playing the roulette of life than in concentrating on their careers.” Gray was with the two of them in Paris when Thomas, after a night out at Le Rat Mort in Montmartre, drank a bottle of mercury bichloride. Pickford, rumor had it, had been prescribed it as a cure for his syphilis. A hotel valet found her the next morning, naked on a sable opera gown spread out on the floor of the Royal Suite.

Moore, Gray, and Pickford stayed by her side at the American Hospital in Neuilly-sur-Seine. She died five days later. The American papers were full of wild innuendo. Even the
New York Times
reported “rumors of cocaine orgies intermingled with champagne dinners which lasted into the early hours of the morning.” The story spread that she had been out trying to score heroin for her husband and that they had fallen out after she had failed to find any. Pickford never escaped the idea that Thomas had committed suicide after having a row with him, though the coroner ruled it was an accidental death. The very same day that the verdict was announced, Gray, Moore, and Pickford traveled together to a memorial service at the Church of the Immaculate Conception in London.

Gray stayed in the UK. Pickford traveled back to the United States. He would soon marry Marilyn Miller, the star of
Sally
who had been working with Clifford Grey only a year earlier. It may have been a small world they were moving in, but it is still striking how the lives of the two Cliffords intertwined. Another odd link: the reason the American Clifford stayed on in the UK was so that he could make a film,
Carnival
, with Ivor Novello, who had been working with the English Clifford only a few months beforehand. It was Novello's first feature film, a remake of
Othello
, shot in Venice and, a touch more prosaically, Twickenham, in south London. Gray had signed on to make three films with the Famous Players–Lasky British Producers.
Carnival
was the first of them, and then he had small parts in
Dangerous Lies
, whose production crew included a young Alfred Hitchcock, and, in 1922,
The Man from Home
. It was the last film he ever made, and the last time he ever acted. He was staying at the Hotel Cecil on the Strand when he was arrested after being caught, bizarrely, in possession of an opium pipe and a Colt automatic pistol. He told the police that the pistol had been given to him by a friend who had just left for America, and explained, a little unconvincingly, that he used the pipe as a cigarette holder.

After that little scandal, Gray drifted, away from London and away from films. He became, in Odd McIntyre's words, “the most consistent of the international gadabouts.” A professional playboy, to put it another way. “Wherever there is excitement,” McIntyre wrote, “Tippy is more than likely to bob up
suddenly, look about pleasantly, and as suddenly vanish.” McIntyre took great delight in regaling his readers with installments of the adventures of this “most ubiquitous New Yorker.” “Tippy fits the vague classification of a man-about-town. Everybody knows Tippy and he seems to know everybody. Wherever you go—Palm Beach, Paris, London, Hollywood, or New York—you will find him. He is natty, boyish, and a wizard thumping piano keys. He appears every inch the irresistible movie hero, and while I have known him a number of years his profession, save that of having a good time, is as nebulous as fog. A sort of human question mark is a fitting description. Tippy is always just arriving or just going somewhere. Not so long ago I talked to him in Los Angeles. He was hopping on a train in 10 minutes for New York. A week later at a New York pier he was going up the gangplank of a liner for Europe. He never seems to light. One night he might be found dining at a lunch counter with a vaudeville acrobat, and the next in immaculate evening dress at the Ritz with a group listed in the social register.”

Of course Gray was a friend of Jay O'Brien's. They knew each other through Irene Fenwick, O'Brien's second wife and an old pal of Clifford's from his Hollywood days. He and Jay were both regulars at Harry's Bar in Paris. Both men claimed to have concocted the Sidecar cocktail, a mix of cognac, Cointreau, and lemon juice, while drinking there. The records are patchy—as McIntyre wrote, Gray was “not the publicity seeker often seen among his ilk. He is just a play-boy, and seemingly having heaps of fun at the job”—but if anywhere was home, it was Paris. A month after he wrote the column in which he described Gray's profession as “nebulous as fog,” McIntyre was surprised to receive an envelope stamped with a Paris postmark that contained only a single business card. It read, simply:

Clifford Gray

Compositeur de Musique

Moulin Rouge Music Hall

Paris

“Tippy” McIntyre wrote, “has put me right.”

In the mid-1920s Gray was working at the Moulin Rouge, writing revue songs for the famous French singer and showgirl Mistinguett. She had just returned from her first US tour and wanted to incorporate a few jazz numbers into her show. Clifford wrote a couple for her, including a foxtrot that he called
“California Rose.” He had always been, as McIntyre noted, a wizard at the piano: “For appreciative listeners he will often occupy the piano chair all night to improvise.” Mistinguett was almost fifty then, “an old lady with young ankles,” though as famous as ever. And as flirtatious too. Not that there was ever a suggestion she and Gray were involved. McIntyre stated his friend was “not a roaming Don Juan. In fact Tippy seems to appeal to the maternal in all women. He is the sort they trust.”

Certainly one did. In 1929 he married Clara Louise Cassidy in Paris. She was the heiress of Charles Whelan, who owned United Cigars, a man then reckoned to be worth around fifteen million dollars. The Whelan family moved to Paris and began living high on the hog. They had started poor but had done so well in the tobacco business that they were able to spend one hundred thousand dollars on the wedding of their second daughter, making it, in the words of the
Schenectady Gazette
, “one of the most elaborate society affairs seen in years.” Clara had been married before, to her father's business partner, John C. Cassidy, and had five children with him. They'd divorced after seventeen years together. It seems she latched onto Clifford, or he onto her, in the immediate aftermath of the separation. The brief marriage notices described Clifford as a “musical comedy producer from Chicago,” which seemed as good a formal description of what he did as any other. With Clifford Gray, the details are always vague.

The marriage didn't stick. Neither did the Whelan family fortune: they lost everything in the fallout from the Great Crash of 1929, almost at the time when Clara and Clifford were getting married. Clara's grandnephew, Frank Whelan, remembered how his grandfather used to tell stories about “yachts, big houses, and servants,” but he always ended them with the phrase “but that was before 1929.” Frank remembered how he'd once seen “my father look at the paper one day and throw it down in disgust and stare into space. In the space of one day he had lost several million dollars.” The family had to cut their cloth to suit after that. “We're all going to have to live a little more simply now,” Charles told his children. It was, Frank wrote, “Bye-bye Paris, hello Jersey Shore.”

Clara had a nervous breakdown not long after and ended up in hospital. Clifford Gray drifted away. Soon he was back, McIntyre wrote, living as “a plump bachelor,” “a lone wolf among globe trotters. He knows almost everybody but nobody seems an intimate. He is a side-line looker-on at life, gazing with the detachment of a modern Punch and murmuring the same immortal line, ‘What fools these mortals be!'” It's not clear if he and Clara actually divorced. She was still going by the name “Whelan Gray” as late as 1938.

Gray returned to what McIntyre described as “the blow-torch life,” only now it was more extravagant than ever. McIntyre claimed to have heard reports of people bumping into Tippy “moseying out of a movie theater in the Bronx,” “on the veranda at Shepherd's in Cairo,” “casually strolling the Shanghai bund,” in “the South Seas, Singapore, and the Arctic circle,” and a “Gibraltar bazaar.” Gray was, McIntyre added, “the man-about-the-globe,” a “zooming devastator of space.” And of course he met him in St. Moritz, too, where Gray “won trophies for his skiing.” Which was news to at least one of his pals, the journalist Arthur “Bugs” Baer. “I never knew Tippy to go in for the outdoor life unless it was an estaminet table or a garden party. Even at the Coconut Grove, he benched out every dance.” But then we shouldn't be surprised by the contradictions and confusions. Gray was the “anthology of human paradox,” noted McIntyre. “Loving life, he seems constantly fleeing from it.”

There were few faster ways to flee than by riding a bobsled—which could well be why Tippy responded to Sparrow Robertson's column when he saw it, in one of those idle estaminet moments, in the
Tribune.
In January 1928 he set off for St. Moritz, to meet up with Jay O'Brien, his drinking buddy from Harry's Bar. Jay duly roped him into the US bobsled squad. Gray was a big man after all, his waist well upholstered after all his hard living, and the sleds needed ballast.

As for his English namesake, who knows? He may have been in Switzerland that winter—it wouldn't be the most surprising of the many coincidences in this curious tale. One thing is for sure though: Clifford Grey never got into a US bobsled, and he never raced with Billy Fiske.

Sunny Corner, St. Moritz, 1927.

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