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Meet Diamond Lil: the gay drag artist who entertained London’s East End during World War II

Our world was pockmarked with bomb sites but Lil was the one piece of true glamour on the street

Meet Diamond Lil: the gay drag artist who entertained London’s East End during World War II
Diamond Lil at the center of the crowd on VE Day on Columbia Road.

If I sat on the doorstep and waited long enough she would appear. There was no regularity to Lil’s morning procession down the street. It depended, I learnt, on how late she had gone to bed the night before.

Her blonde hair would be wrapped in an ornate turban, her slippers were always immaculately outrageous and for a while she had carried beneath her arm Fang, the miniature poodle who wore more faux jewellery than Lil did at that time of day. I would run over and hover by the door as she entered the paper shop to collect her copy of the Daily Mirror.

The owners had placed a stool upon which she would perch and regale them with tales of her nights singing in the pubs and clubs of the East End. Lil had a very long cigarette holder which she used as a baton to accompany her performance, the smoke from the cigarette tracing complex patterns in the air as she spoke. She was exciting, entrancing and wonderful.

The world around us was pockmarked with bomb sites, our homes blackened by a century of soot and smog but amidst this was Lil, the one piece of true glamour on the street.

How could that gilded creature be like my dad?

One day I came home from school with a black eye. Mother treated it with witch-hazel, goodness knows why. I suppose the pain was supposed to ensure that I didn’t fight again and indeed it was eye wateringly awful.

‘What happened?’

‘Some boy at school said Lil was a bloke, so I bopped him one.’

‘And he bopped you back?’

I nodded. Mum sat me on a kitchen chair and sat opposite taking my hands in hers. Her look was concerned as she conjured her words with care.

‘Lil is a man love.’

‘No she’s not.’

‘She’s really called Harry Young.’

I refused to believe her. How could that gilded creature be like my dad or brother? How could Lil have honed the sharp edges of manhood into the soft curves of womanhood?

‘Ask your grandmother Isabella if you don’t believe me,’ Mum said kindly.

‘Lil likes men. There’s people who are like that’

I knew that Nan sang with Lil in some of the pubs and I knew that she would tell me, but I wouldn’t be seeing her until Saturday which was almost a week away. I stared at Mum who by now understood that she would have to tell me otherwise I would pick at it like a sore.

Lil had always been there on the street, she was part of the architecture of life. I had sometimes noticed people snigger as she passed, but had assumed that it was jealousy at her startling looks and sashaying hips.

Mum said that until 1924 Lil had been plain old Harry, a 14-year-old teenage boy with scuffed knees and a snotty nose.

‘Then on the final day at school Harry came back after lunch dressed as a woman. He’d been secretly buying women’s clothes for ages, and prancing about at home in high heels and dresses when everyone was out.’

Mum paused unsure as to how to proceed. I give her credit for carrying on.

‘See love, Lil likes men. There’s people who are like that.’

I asked why? She shook her head.

‘I don’t know. I doubt if Lil does. Still there’s no harm in her and she’s a kindly soul.’

On this point I had to agree but from then on I watched her more acutely and I noticed that her voice was that of a man’s. It was the one thing she never disguised.

‘Everyone knew she’d get no tricks’

She lived in Guinness Buildings on Columbia Road with her partner Maisie, only of course nobody would have used that phrase back then. I suppose I should have realised that all was not as it seemed, that Lil was not our own local Lana Turner by observing Maisie.

Chalk and cheese comes to mind. Whereas Lil was statuesque and beautiful, Maisie was anything but and in drag she was a joke. Short, rotund and with an ability to put on lipstick reminiscent of a car crash, she would mince along the street. Rather than the elegant high heels that Lil wore, Maisie chose plimsolls which were held on with elastic bands.

Many years later an aunt of mine told me how she had once seen Maisie plying for trade at Liverpool Street directly opposite the Police Station.

‘Wasn’t that dangerous?’ I asked. ‘Given that homosexuality was illegal.’

‘Don’t be daft,’ Charlotte replied. ‘Everyone knew she’d get no tricks. The police ignored her, would have been a waste of their time to bother.’

Many a serviceman from overseas had a tale to tell after meeting her

Maisie, when he was George, was a talented French Polisher and must have passed as straight because he’d been in the services. Lil had tried to enlist during the war, but unable to eschew makeup, twin-set and pearls had not gotten in.

Lucky for the area she hadn’t because she kept morale up during the darkest hours. Many a serviceman from overseas who stumbled into London’s East End for entertainment had a tale to tell, or a secret to keep, after meeting her. At war’s end Lil had taken a beer crate around the streets upon which she would stand and sing her signature tune ‘I Want a Boy,’ to all and sundry for beer money.

I found this out some half a century later when researching a book about the area. One of my interviewees, who was 11 years old at war’s end, had witnessed this scene. She sang a few phrases from the song to me but had no idea from whence it came.

Diamond Lil on VE Day

Later in life I wrote a musical play about Lil and wondered if I would be able to track down the song. I held out little hope as I emailed the music section of the British Library. I had only the word of an old lady of something she’d heard a lifetime ago and she may have confused it with one of a myriad of other memories that she had gathered throughout her life.

Almost by return of mail a researcher at the Library said he’d located it. The next day a copy of the song arrived through my letterbox. It was from 1920 and is as outrageous as Lil was.

During my research I was also given a photograph of VE Day in 1945, at the centre of which is Lil her arms linked with my grandmother Isabella. On reflection, not the most unusual of friendships.

The pub was populated by Nancy Boys

On Sunday evenings in the summer Mum, Dad and I would wander up Victoria Park Road to a pub where Lil would sing with Mum. The pub was populated by Nancy Boys and I would stand outside with my packet of crisps with the soggy salt in a twist of blue paper and watch the proceedings.

To a man the Nancys were dressed in suave suits, most wore trilby hats and makeup and one in particular was a beauty, nicknamed Chiquita, as he sang the song of that name. They would entertain the packed pub until closing time.

Lil was known to carry a knife

Unlike Maisie, Lil had no profession but had a string of menial jobs in the area. She cleaned pubs, goodness knows what the supposed ghost in the Nag’s Head on Hackney Road made of her.

She’d served in the pie and mash shop on Hackney Road but had two rather intriguing modes of employment. One, during the war was pushing barrow loads of service uniforms from the factory where they were made, to another down the road that did buttonholing. The other was pushing a cart in Spitalfields’ Fruit and Vegetable Market.

I mention these because I am assured that she did these in full female regalia, something that would be foolhardy even in today’s supposed climate of tolerance. It seems that nobody minded for as long as she and Maisie stayed within the manor of Bethnal Green and a part of Hackney, they were safe. Up-West, where they ventured occasionally, was another world and one from which they would sometimes return beaten and bruised.

It can’t have been all honey in the East End however, as Lil was known to carry a knife. It was only pulled, it was said, when inquisitive and overly friendly strangers wandered into the pubs which she frequented.

Lil was seen throwing her frocks and shoes out of the window

Her wardrobe was massive, full of garments of which she was rightly proud. Once a fire broke out in the flats in which she lived and Lil was seen throwing her frocks and shoes out of the window before surrendering herself to a perplexed fireman on a ladder.

We kids loved both of them. They were kind, funny and always had time for you.

Photos of Maisie were on display everywhere

My last recollection of Lil was when I had a Christmas job in 1970 delivering post. I had a parcel for her and she invited me in for a cuppa. Maisie was not in evidence but Lil and I sat and chatted about love, life and the universe. She had a hacking cough and everything was stained with nicotine, especially her fingers and teeth and she was not long for this world.

The old days of performing were long gone and she’d made a concession to age in wearing trouser suits. Her hair was now a shorter version of the peroxide curls she once displayed, but the diamante jewellery shone as brightly as ever. Photos of Maisie were on display everywhere, I nodded towards them. She answered with one of those indescribable shrugs which carried a lifetime’s worth of love and regret.

I am pleased that Lil passed on before Maisie, because Maisie’s end would have destroyed her. No matter that they argued constantly and were at loggerheads for much of their relationship, there had been huge affection there. They had parted company for reasons nobody knew and that was as much as I knew when something happened which made me reconsider the possibility of fate.

‘He was only a poof to the police’

In 2006 Carol got a job at an insurance company in the City of London. The operations manager was an ex-Bethnal Green boy called Danny to whom she gave a copy of the book I had written about the area surrounding Columbia Road. Five minutes later he came over, the book opened to a section about Lil and Maisie.

‘Here, that Maisie was my uncle Georgie.’

It was in this most unexpected of fashions I found the end to the cycle of their lives.

Not much later I sat in a wine bar in the City with Danny’s sister, Maisie’s niece, Lesley. Danny wasn’t present, he was still unable to cope with what had happened to his uncle.

‘We’d not heard from Uncle Georgie which was strange. It was Christmas Eve and he usually came around to us. So Dad went around to see him, he had a flat on Old Ford Road. Dad couldn’t get an answer but the small bathroom window was open. So he came back and got me as I was small enough to climb in.’

She opened the door and let her father into the place. They’d followed a red trail from the bedroom to the lounge, where Georgie knelt crouched on the floor naked, clutching a crimson sheet sodden with his own blood. His head had been bashed in. He was still alive, but died in the ambulance on the way to hospital. It seems that he had taken someone home who had robbed and beaten him.

Nobody has ever been found for the murder for as Lesley said, ‘He was only a poof to the police. They didn’t even bother to look.’

If you were part of the tribe, you belonged

The East End was known for violence and inflexibility of attitudes. But if you were part of the tribe, you belonged.

Maisie’s death was tragic because even though she’d only moved half a mile away from Columbia Road, she was no longer within the community with whom she’d grown up and where she was accepted.

Strangely anonymous to her neighbours she had been there for at least 48 hours in the freezing cold before her family had found her.

This extract is from Columbia Road: Of Blood and Belonging by Linda Wilkinson. You can purchase the book here.

Linda Wilkinson was born on Columbia Road in East London. She became an author after a career in medical research. She was involved in gay lobby organisation Stonewall and was UK chair of Amnesty International for six years. Linda and her partner were one of the first couples to sign the Greater London Authority’s Partnership Register in 2001. That helped pave the way for civil partnerships and marriage equality in Britain.

Editor’s note on dead naming: To the best of GSN’s knowledge, Diamond Lil and Maisie did not wish to transition. Where appropriate for the narrative, we have therefore left references to their male names. These were sometimes used by those who knew them best and loved them.

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