The Little-Known Truth About Judy Garland’s Ties To These Infamous Gangsters
It’s the Swinging Sixties, and Hollywood legend Judy Garland is dancing in a London nightclub. Little does she know that she’ll soon be privately serenading a big fan with a rendition of the song that made her famous. And that devotee is connected to two of the best-known faces of the day – who just happen to be notorious gangsters.
Garland’s first blockbuster film, The Wizard of Oz, had brought her huge fame while still in her teens. But her life would not quite be untroubled, and it featured plenty of parties, drama and generally overdoing things. Her storied life also featured several of the era’s bad boys, with whom she had no qualms about associating.
Garland’s path through life had brought her to London, specifically Chelsea, the epicenter of swingingness in the capital of cool. There she’d party with Pink Floyd, hang with the Rolling Stones and even boogie – apparently minus her panties – in The Beatles’ most-loved night-time haunt. All in all, it was a long way from Kansas.
Of course, with apologies to Dorothy, the star’s life journey had actually begun not in Kansas but in Grand Rapids, Minnesota. Frances Gumm – her real name – had started as a performer at kindergarten age. Soon she was part of the family song and dance act, which her parents took to California in search of fame and fortune. And it wasn’t long before Garland found it, signing up with MGM in her first year as a teenager.
The studio poured effort into molding Garland into a star. This had an effect on the youngster, leaving her with troubles with drugs that lasted her whole life and a fight for health in both body and mind. Famously, the hardworking starlet had to celebrate her 16th birthday two months before the real date because she was so busy.
The effort paid off with Garland striking gold as a teen star. She lit up the screen in 1939’s evergreen The Wizard of Oz. Garland’s endearing turn as Dorothy scooped her an Oscar for Outstanding Performance by a Screen Juvenile, the only Academy Award she’d ever win. A few years later, she recaptured hearts in smash-hit Meet Me in St. Louis.
Garland’s acting career had, though, peaked with that film, and it wasn’t until the 1950s that she’d once again taste real success. That came with A Star Is Born, which caught the attention of the Academy. But fate decreed that Garland would not bag the Best Actress Oscar for which she had been nominated.
It’s perhaps as a live singer, though, that Garland gained her greatest fame. The 1961 recording of her legendary performance at Carnegie Hall won her five Grammys and sold like hotcakes. It capped a career as a performer that had seen her top the charts many times and sell out venues worldwide.
Yet away from the stage, life didn’t run as smoothly for Garland. She went up the aisle on five occasions, but she’d never really find lasting love. Her first marriage was to David Rose, a composer, when she was only 19. Perhaps her most successful liaison was with Sidney Luft, which lasted 11 years, although not necessarily always happy ones.
But there was plenty of friendship in Garland’s life, particularly from gay men. She spent many happy nights in gay bars along with her buddies. They included George Cukor, Charles Walters and Roger Edens. This was a factor in her being seen as a “gay icon,” with magazine The Advocate suggesting she was “the Elvis of homosexuals.”
Gay men weren’t the only slightly risqué companions with whom Garland spent time. No, she also liked to hang out with gangsters, including Las Vegas bad boy Mickey Cohen. When Tere Tereba wrote a biography of the villain, she said, “Whenever Judy Garland had problems with her husbands she went to Mickey Cohen.”
The pressures of stardom sometimes weighed heavily on the star, so she found relief by hiding out in London. Well, not quite hiding out. When she went there in 1951, her career stuttering, she performed at the Palladium theater. She was a huge hit,with The Daily Telegraph newspaper’s reviewer hailing her by writing, “She gave a more vital performance than anyone I have heard.”
Garland acknowledged that the visit had revitalized her. She said, “Hollywood thought I was through, then came the wonderful opportunity to appear at the London Palladium, where I can truthfully say Judy Garland was reborn.” Indeed, she was, with her stellar performance in A Star Was Born the result.
Garland came back to the Palladium in 1964 appearing alongside daughter Liza Minnelli. This time, her career in Hollywood was pretty much over, so she stayed in London. And with the Sixties very much Swinging, she got into the party spirit that made the U.K.’s capital the grooviest place on Earth.
The superstar lived in the same street as Brian Jones of the Rolling Stones, who shared a flat with The Pretty Things singer Phil May. She hung out with the rockers, getting up to high jinks. One particularly outrageous evening with May ended memorably, as the singer explained to The Daily Telegraph, “So we danced the night away, Judy with her dress over her head and no drawers on.”
A big pal of Garland’s in those days was drag legend Danny LaRue. His club in London’s Hanover Square was a much-loved haunt of the stars. Garland would take the stage alongside LaRue, and the pair would serenade the likes of Zsa Zsa Gabor, Warren Beatty or Elizabeth Taylor there. And among the famous faces with whom she hung out were the Kray twins.
Ronnie and Reggie Kray had moved from the world of boxing, where Reggie had been a pro, into protection rackets. In the mid-1950s they were extorting shop-owners, working out of their base at the Regal pool hall in London’s East End. And they didn’t plan to stop there, seeing their future as big names in the big city.
The twins brought together a heavy-duty gang, which was known as “The Firm.” Soon they had a reputation for violence, and their life of crime was certainly paying off. By 1957 they’d expanded into owning a nightclub, the Double R, which Garland would later visit, and she was by no means the only well-known figure to do so.
While Garland was playing the Palladium and hanging out with LaRue, the Krays were menacing the West End, London’s commercial and entertainment district. Their hold on the East End was fierce, backed by violence that extended into murder. They even made connections to American crime figures such as Angelo Bruno, the Philadelphia Mob supremo.
But the Krays did not only want to be famed in the twilight world of crime. They also wanted to be known by everyone else, too. You could consider them ultimately to have been unsuccessful as criminals, given that they ended up in jail for life, but they succeeded in creating a name for themselves.
Their mom Violet’s hairdresser Maureen Flanagan shared with U.K. newspaper The Guardian in 2015 what motivated the twins. She said, “The protection racket was their game. But it wasn’t just for money, it was for prestige, status. Ronnie loved celebrities.” And they’d be seen around town with plenty of well-known names.
Among them was Joe Louis, one-time world heavyweight champ. The Krays took him from club to club, getting him to sign people’s boxing gloves. Meanwhile, Ronnie spent time with George Raft, who’d starred in the 1932 gangster flick Scarface and now ran a West End casino. Among the British stars who were snapped alongside the twins were actresses Barbara Windsor and Diana Dors.
A source interviewed for 2021 U.K. TV documentary Secrets of the Krays explained why people wanted to be seen with the gangsters. They said, “The Krays were extremely violent people, but there’s a glamour to crime as much as there is a glamour to somebody from the theater or film.”
The source continued, “It’s clear that certain people saw it as a badge of honor to have their picture with the Krays, as much as the Krays saw it as having a picture with them.” Indeed, the brothers in crime were such big names that renowned snapper David Bailey took a photo of them for a celebrity collection in 1965.
So it’s no wonder that stars flocked to their nightclub. A-listers as renowned as Frank Sinatra – no stranger to the world of gangsters – could be seen there. Politicians and socialites also turned up at the Krays’ nightclubs. At the height of their powers, the twins owned several nightclubs, forming the legitimate side of their business.
Glamour, sparkle and a party? Well, in the 1960s, Judy Garland wouldn’t be far away. And she was one of the celebrities whose path crossed that of the Kray twins. But not every celebrity would find themselves invited to the Krays’ family home at 178 Vallance Road, where the twins lived with their mom, incredible as that sounds.
When Garland visited a Kray club, the notion came to Ronnie that she should come to visit their mom. After all, she had sung Violet’s most-loved song. Yes, the Krays’ mother had a special liking for “Over the Rainbow.” So Ronnie is reported to have said, “We have to have Judy Garland in our presence,” according to the article in The Guardian.
So the twins did something quite astonishing and invited Garland around for tea! And as you can imagine, not many people said no to the Krays; the star of The Wizard of Oz wasn’t about to buck the trend. She turned up at Vallance Road, and as Violet later told a friend, “I sat her down and gave her a cup of tea.”
Well, you don’t just have Judy Garland in your house every day, so Ronnie suggested that she perform for them. A source told the documentary Secrets of the Krays, “Ronnie said, ‘You know that song you sing, you sang in the film, that’s my mother’s favorite song.’ And she’d say, ‘Your mum don’t want to hear me sing, there’s no music or anything.’”
But the Krays wouldn’t take “no” for an answer. After all, Garland didn’t really need musical accompaniment to perform a song that she knew so well. So with everyone gathered around, she sang “Over the Rainbow” for Violet Kray. It may not quite have been the Palladium, but she certainly had an audience to remember.
And what did mother Kray think of the performance? Well, it seems that she wasn’t all that impressed by the singer. She apparently said, “She was a frightened little thing, too skinny.” Nothing else is known about the visit, so we don’t know what the four of them talked about or whether Garland performed an encore.
All in all, though, Garland seemed to have fared better than she would a bit later, when she started singing in a pub near to a Krays establishment. She wouldn’t allow herself to be taped, which didn’t please the people who were drinking there. They rocked her Rolls-Royce as she attempted to get away.
At least Ronnie was left with a favorable impression. When he was on trial for murder some years afterwards, he seemed to recall the occasion with pleasure. He told the judge, “If I wasn’t here, I could be having tea with Judy Garland.” The judge does not seem to have been particularly impressed, though.
In fact, the judge gave Ronnie a life sentence for his part in gangland murders after a police investigation came up with compelling evidence. Even though the twins had previously gone free when they’d scared witnesses, this time threats would not work. They were handed a minimum of 30 years in jail, a sentence then of unprecedented length in the U.K., in 1969.
The twins would not serve their sentences together. This was largely because Ronnie was transferred to a facility for prisoners with mental illness. But the two of them proved stand-up citizens in jail, both learning oil painting. Reggie did a lot of work for charity from his cell and spent a lot of time answering fan mail.
Reggie was allowed out of jail in 2000 since he was in the grip of cancer that would soon end his life. But Ronnie didn’t ever leave custody: his heart failed in 1995. But even though they were gone, the twins were not forgotten. They may even be more famous today than they were when they were alive.
The Krays have been featured in several documentaries and have had two more semi-fictional movies made about them: 1990’s The Krays and 2015’s Legend, the latter starring Tom Hardy as both twins. The 2021 documentary Secrets of the Krays features the Judy Garland story. Coming nearly half a century after the events that it portrays, it shows the fascination they – and Garland – still hold for U.K. viewers.
As for Garland, when the 1960s came to an end, she found herself destitute, her money all gone to the I.R.S. It seemed Hollywood no longer had a place for her – but London did. She scored a five-week residency at the Talk of the Town nightclub. It paid £3,000 a week, equivalent to a bit more than $70,000 at the time of writing in 2021.
But it didn’t go well. Garland began the run of shows at year-end 1968 but by the end of January, she was too ill to carry on. For the last show that she played, she turned up late and quit early. She wasn’t able to sing “Over the Rainbow” all the way through, which displeased the audience so much that they bombarded her with bread rolls.
Some of the shows that Garland managed in January 1969 had been full of the old magic. But some had been a terrible mess. It was a sad way to end a glorious career. Her last date came in Copenhagen in March that year. A few months later, she passed away at home in London, little more than 30 years after her triumph as Dorothy.