In 1974, Andy Warhol landed a $1m commission from Italian art dealer Luciano Anselmino. His brief was to forsake the soup cans and superstars that had made his name and take a walk on the wild side, creating portraits of New York’s hidden community of drag queens. Too famous to track them down himself, he sent his young acolytes out to a club called the Gilded Grape, which was the haunt of a largely black and Latinx crowd.

So began one of Warhol’s most touching and less-known projects. Ladies and Gentlemen is a series of 268 vibrantly coloured silk screens, 25 of which will make their first UK appearance this month, alongside Mao and Marilyn Monroe, as part of a retrospective at Tate Modern. Of the 14 sitters featured in the series, a couple were well known on the gay underground, but most were not. Though they all signed their drag names on the Polaroids from which the pictures were created, the stories of Broadway, Lurdes, Helen/Harry Morales et al have only gradually emerged through decades of research by the Warhol Foundation.

One of Warhol’s scouts was Corey Tippin, a 24-year-old actor and makeup artist. “I would go there and find particularly beautiful women and tell them that they’d get paid $50 – a lot of money back then – and it didn’t involve anything sexual. They just had to be ready to be picked up in a taxi at 10 in the morning, which I didn’t think they’d manage, because most of them were sex workers and they lived by night. But they all showed up.”

One of the models Tippin discovered was “a very petite, soft-voiced transexual” called Iris. “She had a pretty little wig but also posed for some of the pictures without it.” Iris features in eight of the pictures that will be shown at the Tate, in two different poses. One, with her fingers framing one eye, was known in fashion circles as “the search”. The other, with her arm draped languidly over her head, was dubbed “the Wilhelmina”, in honour of another sitter who directed the poses and who, Tippin believes, even snapped some of the Polaroids.

The glamour and theatricality of the pictures conceals the hardships that the drag queens suffered. Like many of them, Iris had a missing tooth, which Warhol painted back in for her. “Andy gave her back her tooth,” says Tippin, who holds this small kindness as evidence that the project was not simply exploitative. Iris was very particular about the way she wore her blouse, “which made me suspect she was on bootleg hormones and was proud of her little breasts”, says Tippin.

“These were very different times. The idea of drag queens who actually considered themselves women hadn’t come into consciousness, even among most doctors, so they would buy drugs on the black market and many of them got sick. They didn’t have much money, but they had so many little theatrical tricks: the will, the transformation, the risk. They really were my heroes.”

While most of the sitters had no idea who they were posing for, that was not true of Wilhelmina Ross and Marsha P Johnson, who had both been part of a drag troupe called Hot Peaches. Founder and director Jimmy Camicia recalls putting on their first shows in the loft of Warhol superstar Jackie Curtis, although he was sceptical about the Factory, and in 1973 Hot Peaches sent it up in The Magic Hype drag show, starring the celebrity-obsessed sell-out Randy Whorehall. “When you were inside that circle it didn’t look like it did from the outside. In fact, it looked very tacky and exploitative, so that’s how we showed it,” says Camicia today.

He gave everyone the potential to be beautiful, to feel good under their protective mask

By the time Camicia met Marsha in the early 70s, she had already played a key part in the 1969 Stonewall uprising and was leading the Street Transvestite Action Revolutionaries with her friend Sylvia Rivera. “She was out of the box,” says Camicia. “She’d panhandled on the street but she gave most of her money away.” The P in Marsha’s name stood for “pay it no mind”, which she reputedly told a judge who questioned her gender, charming him into acquitting her on a minor felony, “probably loitering”.

Wilhelmina turned up a couple of years later, “playing a cockroach in a really tacky downtown show”, says Camicia. “She was dressed in this glamorous gown and I thought, what the hell, I’ve got to meet that cockroach. She wouldn’t tolerate bad language. She had this ‘code of elegance’ and she stuck to it, probably to her disadvantage.” In vintage footage from Hot Peaches shows, Wilhelmina shimmers in flounced white sateen as “drag queen superstar Belladella Bosom”, purring “I’m not a woman, I’m not a man, it’s my own game”.

Wilhelmina had the biggest presence in the Ladies and Gentleman series, appearing in 73 paintings, two of which will be at the Tate. “I didn’t expect that and I was astonished. I started to wonder if Andy was fascinated by her,” says Camicia. In 1975, when the series was completed, Wilhelmina also had a bit part in The Happy Hooker, a film that was supposedly about the right to be a prostitute which underlined the prejudices black hustlers were up against by representing them as a caged rabble. Warhol, in contrast, released their inner superstar. As art curator Stephan Diederich writes in the Tate catalogue: “He allowed everyone the potential to be beautiful, to be able to feel good under their protective mask.”

None of the Ladies and Gentlemen sitters are believed to be still alive. Wilhelmina, says Camicia, “had a very bad ending, addicted to crack cocaine and sleeping on the streets. She didn’t want to go on welfare and pushed and pushed until she got a job, but they gave her a really hard time and finally she couldn’t take it any more.” Iris was last spotted in Paris, where she is rumoured to have disappeared after getting into a fight while working in a drag show alongside the French film star Jean-Claude Dreyfus.

Marsha lived until 1992, when her body was found floating in the Hudson River. An initial verdict of suicide was overturned in 2012 after New York police accepted that she was probably murdered. Marsha, at least, has a place in history: last month it was announced that a Brooklyn park would be renamed after her, while in 2021, statues of her and her friend Sylvia Rivera are due to be unveiled near the site of the Stonewall Inn in Greenwich Village – making them the first transgender activists to be honoured with public monuments.

How would the ladies and gentlemen feel about finding themselves occupying their own room at Tate Modern? “Wilhelmina would be thrilled that we’re all talking about her. Marsha wouldn’t care. She was part of a much tougher crowd,” says Camicia. Together, the 25 portraits – with their jagged energy, their blurs and splashes of colour – conjure up a brave and vivacious community. “I just wish they could realise how immortalised they’d be,” says Tippin. “They’ve become icons of a very special time in the history of something which is so very prevalent today.”

Andy Warhol is at Tate Modern, London SE1, from 12 March to 6 September. There’s a 2-for-1 ticket offer for Guardian and Observer readers. Visit tate.org.uk/warhol-2020 and use code “GUARDIAN241”. Offer valid until Wednesday 11 March

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