You Better Work: Classic Rockers in Drag

I love many things besides classic rock. One of the things I love almost as much as classic rock is drag, especially shows like RuPaul’s Drag Race and Dragula.

Over the past few years, Drag Race has exploded in popularity, and fans have been spoiled this year with multiple seasons of the show: All Stars 3, Season 10, the Holi-Slay Spectacular, and All Stars 4. Also in the news, RuPaul’s Drag Race is coming to the UK next year! Exciting to see what this brings to the table. The Christmas special and AS4 are coming out this month, so what better time to write this?

In this post I’ll be sharing a bit about the history of drag and then talking about classic rockers who crossdressed. Let’s go!

The Her-story of Drag

One of the best YouTubers who explains the history of drag better than I can, is Jaymes Mansfield. She was a contestant on Season 9 of Drag Race. I’ll sum things up as quickly as I can. I’d also recommend watching the films The Queen from 1968, Paris is Burning from 1990, and The Adventures of Priscilla, Queen of the Desert from 1994. These are some of my favourite drag related movies besides Rocky Horror Picture Show.

In drag, there are drag queens (aka female impersonators) and drag kings (aka male impersonators). There are many different styles of drag:

  • Androgyny (Nina Flowers, Milk) – Are you a boy or are you a girl? Who cares!
  • Club Kid (Vivacious) – Inspired by the 80s/90s NYC Club Kid scene.
  • Goth (Sharon Needles, Vander Von Odd) – Basically Halloween, but every day.
  • Pageant (Alyssa Edwards, Alexis Mateo) – Fierce looks, big hair.
  • High Fashion (Aquaria, Violet Chachki) – Like a runway model.
  • Camp (Tammie Brown, Bianca Del Rio) – Funny, exaggerated, and bold looks.
  • Punk (Adore Delano) – Not caring what others think. Drag your way.
  • Fish (Courtney Act, Farrah Moan) – Drag queens that look straight up like women.


Drag has been a part of performing arts history since ancient history. Crossdressing was seen in Ancient Greece, the Middle Ages in Europe, Shakespeare’s time, and the Edo period of Japan.

The term drag wasn’t really used until the 19th century, with the origin of the term coming from long skirts dragging on the floor.

Because many of these rock stars we’ll be talking about are British, it’s important to talk about the British history of drag. British people will be very familiar with Pantomime, which is a type of musical comedy theatre that features a lot of crossdressing actors (pantomime dames), men wearing wigs, makeup, and dresses for comedic effect. The first pantomime opened in 1723.

The 20th century to today:

The culture changed by the 20th century as more and more gay and bi men came out of the closet and people started associating drag with homosexuality, so it got pushed underground. In the US, there were laws against crossdressing on the books as recently as the 70s. Drag queens and trans women were there from the beginning in the gay rights movement, with Sylvia Rivera and Marsha P. Johnson founding STAR, Street Transvestite Action Revolutionaries, an organisation that helped homeless LGBT youth. Both Rivera and Johnson were at the Stonewall Riots in 1969.

In more modern days, there’s Monty Python, Kids in the Hall, and Mrs Brown’s Boys. So it’s not just a British thing. These comedy shows all have crossdressing characters. In the 70s and 80s, Divine was in John Waters films, Multiple Maniacs, Pink Flamingos, Female Trouble, and Hairspray. Divine was the inspiration for Ursula in Disney’s The Little Mermaid.

In 1994, RuPaul was the first drag queen to be the face of a major cosmetics company, with MAC Cosmetics. That was huge. Love or hate RuPaul, there’s no doubt he had a lot of influence and helped launch the career of many drag queens.

And of course, there are drag competitions like RuPaul’s Drag Race (2009-present) and The Boulet Brothers’ Dragula (2016-present).

The Influence of Drag:

Drag has really exploded in recent years and has influenced mainstream culture. I remember when I was 13, a classmate told me I looked like a crossdresser, which was intended as an insult. Today though, it’s not. Drag queens have influenced fashion and beauty.

For example, a lot of Instagram makeup looks today are based on things drag queens typically do: contouring and highlighting, overdrawing lips, “baking” with setting powder, cut creases, stacking a bunch of false lashes, and using tape or a business card for precise lines.

The slang is influential and you’ll hear young people using it every day: beat, biiiiiitch (gotta say it that way too), clock, crusty, feeling my oats, fierce, for the gods, good god get a grip girl, halleloo, hunty, jush, kiki, mug, no tea no shade, purse first, read for filth, realness, shade, tea, vanjie, yaaas, and you better work.

Drag FAQs:

What pronouns do I use for a drag queen? Depends on the queen. In drag, you refer to her with female pronouns. Out of drag, it depends. If she’s a trans woman (or cis woman), use she/her. If the queen’s a man, use he/him. If the queen’s non-binary, use they/them.

So do they want to be women? No. Some are cis men, and are very much dudes, they just like to play a character. Others are trans or cis women, and they are women, their drag persona is a character too.

Are all drag queens gay? No. Most of them are though. There are also quite a few bisexuals who do drag. Anyone of any gender or sexuality can do drag, however it takes a lot of work. RuPaul’s Drag Race is arguably the biggest drag platform, but it is criticised for being limited and not showing all kinds of drag.

Do straight guys and lesbians find drag queens attractive? Can’t speak for anyone other than me, but I’m sure there are many who do. I find a lot of drag queens attractive.

What’s the money like? Like in any creative field, not great for the most part. You do drag because you love it, not for money. Most drag queens have day jobs. Very few make enough money from drag to pay their bills and drag is not a job with a 401k, insurance, and benefits.

The good news is most of the queens on Drag Race go on to have successful careers and do drag full time. That said, it’s an expensive hobby: Wigs are expensive especially big drag ones. Many of their dresses and jumpsuits are custom made (that can cost anywhere from a couple hundred to thousands of dollars). Makeup gets expensive (you go through a lot more than an average makeup wearer). And you might want to pad or cinch – padding isn’t totally essential if you’re slim and going for the runway model look, but you’re gonna want that waist to be snatched for the gods. Don’t buy one of those crappy waist trainers that the Kardashians shill, they’re useless. A steel boned corset will cost at least $100 (although good ones can be found for as little as $50 or $60, yes even brand new), don’t worry you’re not gonna die and it’s actually not that uncomfortable (it’s more comfortable than a bra). A good breastplate will run about $700 or you can get breastforms for a lot less than that. Hip pads can run about $200 or your can DIY it with some foam, but make sure it’s not lumpy.

There’s a lot of pressure to update your wardrobe and even if you know how to sew, if you’re a busy drag queen you don’t have the time to make all your outfits. You don’t want to be seen in the same outfit too many times. Going on Drag Race has gotten more expensive over the years because the bar keeps going higher and higher. Basic bitch mall drag was okay in season 2, but it won’t fly anymore, Michelle Visage will read you for filth.

Crossdressing Classic Rockers (and musicians of the era)

In this section, we’ll talk about rock stars who crossdressed and if I know the context, I’ll share it with you. For the most part I think these were silly joke photos, but some of these guys would have made great contenders for a celebrity edition of Drag Race.

Alice Cooper: Here’s a picture of Alice Cooper in drag. I don’t have any context.


Annie Lennox: Half of the Eurythmics, she was well known for her androgynous style made famous in the music video for “Sweet Dreams (Are Made of This)”. She was seen as the female equivalent of Boy George.

The Beatles: George Harrison and John Lennon crossdressed at some point.

Fun fact about George: He was good friends with Monty Python, producing the film Life of Brian. That film almost didn’t happen because production companies thought it would be too controversial, but George Harrison believed in it and started the production company HandMade Films.

In the pictures above, George was dressed up as a woman for the Beatles’ Christmas Show. Sadly, there’s no video of this performance.


John Lennon wore a wig in this behind the scenes picture from Help! in 1965. Reminds me a bit of Yoko.

Bon Scott: Bon Scott wore a Pippi Longstocking wig during a 1974 performance of “Baby Please Don’t Go”.


Boy George: Gender-bending 80s icon well known for his flamboyant, androgynous style in the 80s. He said this about his style:

“Now, because I’m a very famous person people accept that I can look male and female. There are a lot of people out in the jungle who still dress the way I do and my job is to make it safe for them to be able to be normal people without being successful.”

Dave and Ray Davies: You mean The Kinks had bisexual band members, sang LGBT songs, and they crossdressed? They might just be the gayest British Invasion band and I’m living for it. In this music video, you can see Dave in drag at 0:30, 1:08, and 1:26. At 2 minutes in you see Ray dressed up as some old lady. The BBC didn’t like the music video. Not because of the drag, but because the video showed slums, poverty, and the band were dressed up as Victorian pallbearers.

David Bowie: Early 70s Bowie was basically drag. Beautiful long blonde hair. He wore a dress on the cover of The Man Who Sold The World. Who needs gender roles when you have David Bowie?

This wasn’t the only time he did drag. He also did drag in the music video for “Boys Keep Swinging”. I love his look with long, wavy, red hair. In the video you can see Bowie strutting on the runway.

Elton John: He’s known for his wild outfits and glam rock dress sense. This picture of Elton John in a gown was taken sometime in the 80s at a concert.

Screenshot 2019-05-17 at 22.42.56

Frank Zappa and The Mothers of Invention: Serving facial hair realness. This picture is from the 1968 Mothers of Invention album We’re Only in it for the Money.


Grace Jones: She was part of the disco scene in the 70s and well known for her androgynous looks that inspired Madonna, Bjork, and Lady Gaga. Bebe Zahara Benet imitated her for Snatch Game. Of her gender she said:

“I go feminine, I go masculine. I am both, actually. I think the male side is a bit stronger in me, and I have to tone it down sometimes. I’m not like a normal woman, that’s for sure.”

Screenshot 2019-05-20 at 14.07.15-min

Iggy Pop: He once said “I’m not ashamed to ‘dress like a woman’ because I don’t think it’s shameful to be a woman.” Well said!

Not taken during the classic rock era, but I love this photoshoot of Iggy Pop with a Dior bag. High fashion!


Joan Baez: Dressed up as Bob Dylan while touring with him on the Rolling Thunder Revue tour. Here are some screenshots of her from the documentary, dressed up as Bob Dylan.

Marianne Faithfull: In the music video for The Rolling Stones’ “We Love You” you can see her in drag as Lord Alfred Douglas, lover of Oscar Wilde. You can see her in the video at 1:42, 2:30, and 2:45.

Mick Fleetwood: On the cover of English Rose, a Fleetwood Mac compilation album released in 1969, he is in drag.


The Monkees: All of the Monkees have been in drag on the show, but everyone’s favourite seems to be Mike Nesmith as Princess Gwen in the episode “Fairy Tale”. That’s my favourite crossdressing Monkees moment.


Don’t fret though if you’re a Davy, Micky, or Peter fan. There are pictures of them in drag too.

Davy Jones was in drag in the episodes “Some Like it Lukewarm” – an episode where The Monkees enter a singing contest, but the contest is only open to mixed gender acts; “Monkee vs. Machine” – where The Monkees try to get a job at a toy factory that uses computers to hire workers and they sabotage the automation; and “Fairy Tale” – an episode where The Monkees act out a bunch of fairy tales. In “Some Like it Lukewarm”, there’s also a woman dressing up as a man. I’d say Davy’s my other favourite Monkee in drag.

Micky Dolenz was in drag in the episodes “Monkee vs. Machine”, “The Chaperone” – an episode where the Monkees throw a chaperoned party and invite Davy’s crush (who has a strict military dad) and Micky poses as the chaperone after the chaperone faints. He played Goldilocks in “Fairy Tale”.

Peter Tork was in drag in the episode “Monkee vs. Machine”.

Peter in drag

New York Dolls: The New York Dolls were known for their androgynous dress sense. They once performed in drag in 1974.

And here’s a picture of them in drag.


Ozzy Osbourne: Here’s a picture of Ozzy in drag in 1984.


Queen: Of course, we can’t forget Queen! The band all did drag for the music video for “I Want to Break Free”. As you can tell from the picture, it was totally Roger Taylor’s idea. I’ll say it. Of all the classic rockers, Roger Taylor was the fishiest (feminine looking) drag queen – probably Courtney Act or Farrah Moan levels of fish. That’s enough fangirling.


I love this gif.

The idea for the IWTBF music video was a drag parody of Coronation Street with Roger playing the schoolgirl, Brian as the mum, Deaky as the grandma, and Freddie as the fabulous housewife with a moustache.

Deaky crossdressed again in this 80s music video for “Stutter Rap”. He appears at 2:41

Brian has been seen in drag on other occasions, like this witchy androgynous look here. Sharon Needles is that you? 😜


Brian also crossdressed at Elton John’s 50th birthday party. Love how he wore a curly wig.

As for Roger, here’s a couple of pictures of him goofing off wearing a wig or a skirt.

Freddie did drag with Roger Taylor and Peter Straker for the music video for “The Great Pretender”.

Pete Burns: Androgynous pop singer from 80s group Dead or Alive and an influential icon. Especially in later years, he looked very feminine.

As for his style, he once said “Everyone’s in drag of some sorts,” and “I don’t give a fuck about gender and drag. I’m not trying to be a girl by putting on a dress – gender is separated by fabric.” He kind of reminds me of Cher in these pictures.

Red Hot Chili Peppers: Anthony Kiedis and Flea were in drag in 1993 at MTV Live and Loud.


Robert Plant: In 1973, while on tour, Robert Plant wore a dress and took a picture with Roy Harper in a hotel.

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The Rolling Stones: The Rolling Stones as a group dressed in drag in 1966, a time before glam rock and when male rock stars looked a lot like women. This photo was for the single “Have You Seen Your Mother Baby, Standing in the Shadow?”.


I think this is from the 1966 shoot (but behind the scenes), but here is a gif of Keith Richards and Brian Jones in drag.


Here’s Brian Jones in a bullet bra, getting ready for the photoshoot:


Here’s Keith Richards in drag:


Of all the band members, the androgynous Mick Jagger seemed to love to crossdress the most. Here are a few of his moments crossdressing:

Steven Tyler: In 2013, he auditioned for American Idol as a joke, calling himself Pepper LaBeija (a nod to the legendary drag queen).


Sylvester: Can’t have a post about musicians of the 60s and 70s who did drag without mentioning Sylvester. He was known for his androgynous dress sense and wore both “men’s” and “women’s” clothes. Throughout his career, he was out as gay. He was in drag for part of the “You Make Me Feel Mighty Real” music video. He was called “The Queen of Disco” in his home base of San Francisco. Before he got famous, he was part of drag troupe The Cockettes.

U2: During the Achtung Baby era the band went to Tenerife, where Anton Corbijn took pictures of the band in drag.

The Who: Everyone in The Who has taken pictures in women’s clothing for a laugh, but Keith Moon really went above and beyond in the band. He looked like he was really into drag. I could picture him in a celebrity version of Drag Race. Keith Moon dressed up as a nun in Frank Zappa’s movie 200 Motels. Dougal Butler, Keith Moon’s assistant described him as a “heterosexual drag queen”. I could definitely see Keith Moon doing well as a comedy queen on a classic rock version of Drag Race.

Here are various pictures of Moonie in drag:

Roger Daltrey wore a dress in this picture that may have been taken in the 80s, I think. Not sure about the context. Walk the runway, Rog!

Roger in Drag

Pete Townshend dressed like a woman at a drugs benefit concert in 1986.

Pete Townshend in Drag

John Entwistle was in drag with Kenney Jones while playing field hockey.

And not quite drag, but here’s John with a purse:

John Entwistle with a purse

Sources and cool links:

Please Kill Me: Rockstars in drag

Monkees in Drag

How Stuff Works: An Early History of Cross-dressing

PBS: Anti-crossdressing laws timeline

Keith Moon in Drag

Another article about Drag Superstar Keith Moon

17 Times Pete Burns Was a Style Icon (And Definitely Knew it)

What’s the Story With This 1966 Photograph of the Rolling Stones in Drag?

In Drag

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