Madonna at 62: The moments that made a legendary career

The pop icon celebrates her 62nd birthday today (August 16).


As Madonna celebrates her 62nd birthday today (August 16), Matt Cain, author of new novel The Madonna of Bolton, offers up a comprehensive history of the Queen of Pop's legendary career...

1) Madonna first came to our attention with 'Holiday', released in the US in September 1983. Aged 25, she revealed her punky style – wearing lace gloves, crucifixes, rags in her hair, and underwear as outerwear

2) A few months later Madonna unleashed 'Lucky Star', dancing in the video alongside her gay brother Christopher Ciccone. Years later, the two would become estranged when Christopher wrote the tautobiography, 'Life with my Sister Madonna'


3) In her earliest interviews, Madonna spoke proudly about her friendships with gay men, such as dance teacher Christopher Flynn and artist Martin Burgoyne, at a time when positive representations of gay men in the media were almost non-existent.

Following Burgoyne’s death in 1986 and Flynn’s four years later – both victims of the Aids pandemic -- Madonna wrote 'In This Life', singing, “In this life, I loved you most of all”

4) In 1984, Madonna performed 'Like a Virgin' at the first MTV Music Awards, appearing on top of a giant wedding cake then writhing around the stage in a low-cut wedding dress, suspenders and BOY TOY belt buckle.

5) 'Material Girl' was released, accompanied by a video in which Madonna recreated Marilyn Monroe’s performance of 'Diamonds are a Girl’s Best Friend'.

6) In April 1985, Madonna embarked on The Virgin Tour, her first live tour of the US and Canada. Much of the press coverage concentrated on the number of people in the audience mimicking her look.

7) In 1985's Desperately Seeking Susan, Madonna nailed her first major film role, playing a drifter who stays in touch with her boyfriend through the personals columns. It also featured 'Into the Groove', her first UK number one single.

8) In July 1985, Penthouse and Playboy published nude photos of Madonna taken in the late Seventies. She declared that she refused to feel ashamed.

9) Just a few days later, Madonna took part in Live Aid, performing a specially written song, 'Love Makes the World Go Round'.

10) The art of reinvention that has defined Madonna’s career made its first appearance in March 1986 in the video for 'Live to Tell'. She abandoned her lacy gloves and crucifixes to reveal a new stripped-back look of golden blonde hair, a demure dress and subtle make-up.

11) A few months later, Madonna released 'Papa Don’t Preach', a song about teen pregnancy. It was accompanied by a video that featured her wearing a T-shirt emblazoned with the slogan 'Italians Do It Better'.

12) In the 1986 video for 'Open Your Heart', Madonna played a stripper with a heart and a strong maternal instinct. But, at the height of the Aids crisis, LGBT+ fans were most impressed by the presence of two gay sailors.

13) The following year 'La Isla Bonita' championed a different repressed minority, the US’s Latino population. The video saw her playing her signature dual role of Good Madonna/Bad Madonna, challenging the virgin/slut dichotomy of her Catholic heritage.

14) A few months later, Madonna was back on our cinema screens in the film Who’s That Girl, a screwball comedy that bombed at the box office, despite the success of its soundtrack. Watch it again now and it’s great fun – and has a gay twist.

15) In summer 1987 Madonna embarked on the Who’s that Girl tour, her first in the UK. She showed off an athletic physique – and black basque and fishnets.

16) In 1988, while Madonna was starring on Broadway in the play Speed-the-Plow, she appeared on Late Night with David Letterman alongside lesbian comedian and then best friend Sandra Bernhard.

The pair dressed in matching outfits, talked about their nights out in lesbian club the Cubby Hole, and joked about having slept together.

17) In February 1989, Madonna appeared in the video for 'Like A Prayer' as a brunette, kissing a black Jesus and dancing in a skimpy dress in a field of burning crosses.

Religious groups were outraged but look closer and you’ll see that the video tells a story about racism, with Madonna playing a witness to a rape for which a black man is unfairly arrested.

18) 'Like A Prayer' was Madonna’s most personal album, which she used to campaign for greater awareness of Aids; each copy carried a leaflet in which Madonna insisted that, “People with Aids – regardless of their sexual orientation – deserve compassion and support, not violence and bigotry".

19) 'Express Yourself' is a rousing anthem to female empowerment and was given a video that featured Madonna cross-dressing and presiding over an army of muscled male slaves.

20) In 1990, Madonna released 'Vogue', a song, video and dance routine directly inspired by gay culture and the Harlem house ball circuit documented in the film Paris is Burning – the same subculture that would later inspire RuPaul’s Drag Race.

21) Later that year, Madonna embarked on the Blond Ambition world tour, unveiling a show that was far more theatrical than anything seen before. It also gave us one of her  most enduring looks: the corset designed by Jean Paul Gaultier.

22) While on tour, Madonna was also busy promoting the film Dick Tracy, in which she starred alongside then-boyfriend Warren Beatty and performed three songs by Stephen Sondheim.

23) In September 1990, Madonna closed the MTV Music Awards with a performance of 'Vogue', dressing up as Marie Antoinette holding court in a French chateau.

24) Madonna rounded off 1990 with the release of 'Justify My Love' and a video that featured scenes of tranvestism, lesbian kissing and S&M.

25) At the Academy Awards in 1991, Madonna channelled classic Hollywood glamour and appeared dripping in diamonds to perform a sexed-up version of 'Sooner or Later', from Dick Tracy, which won Best Original Song.

26) That summer, she released the documentary In Bed with which was shot behind the scenes on the Blond Ambition tour.

It revealed that six out of Madonna’s seven dancers were gay, showing them attending a Gay Pride parade and even French-kissing in close-up. Audiences were shocked but Madonna took the opportunity to challenge homophobia.

27) In October 1992, Madonna released 'Erotica'. It had a much rawer sound than the more polished pop for which she was known and defiantly queer lyrics – and the album’s title track was given a sexually explicit video in which she played a masked dominatrix.

28) The following day saw the release of 'Sex', a coffee-table book of explicit images exploring Madonna’s sexual fantasies. Shot by photographer Steven Meisel, the limited edition of 150,000 sealed copies sold out on the first day.

29) Responding to the torrent of slut-shaming ignited by 'Sex and Erotica', in May 1993 Madonna performed 'The Lady is a Tramp' on The Arsenio Hall Show alongside her then beau, Anthony Kiedis of the Red Hot Chilli Peppers. The pair wore matching devil horns, skirts and suspenders, and their performance is a hilarious gender-fuck.

30) In September 1993, Madonna premiered her latest world tour, The Girlie Show. It opened with a topless dancer sliding down a huge pole and Madonna dressed as a whip-cracking dominatrix, later dragging up as Marlene Dietrich in a top hat and tails to sing 'Like a Virgin', and presiding over a pansexual orgy.

31) In March 1994 Madonna made another notorious appearance on The Late Show with David Letterman. When the host introduced her with a joke about how many men she’d slept with, she let rip with a tirade of expletives.

32) 'Bedtime Stories' was a more subdued album than before but the video for 'Take A Bow', the second single to be lifted from it, still depicted Madonna as the girlfriend of a Spanish bullfighter, sees writhe around in her underwear.

33) Madonna was back in defiant mode with 'Human Nature'. “Express yourself, don’t repress yourself,” she declared in a video that recast her as a sexual provocateur.

34) Madonna lobbied hard for the lead role in the big-screen version of Andrew Lloyd Webber’s musical Evita, and her performance as Eva Peron earned her a Golden Globe for Best Actress in 1987.

35) Madonna’s first release post-Evita was 'Frozen', en epic electronic ballad which was complemented by a video shot in the Californian desert that saw Madonna reinvent as a shape-shifting goth.

36) Motherhood, maturity and mysticism all influenced Ray of Light, released in 1998, which went on to win four Grammys.

37) In May 1999, Madonna had a hit with 'Beautiful Stranger', the theme tune to Austin Powers: The Spy Who Shagged Me. The video sees her playfully seducing lead actor Mike Myers and showcases her mischievous sense of humour.

38) The Next Best Thing should have been Madonna’s greatest triumph as an actress. She appears alongside Rupert Everett as a yoga instructor who has a baby with her gay best friend but the film flopped.

However, read Everett’s autobiography to find out how passionately Madonna believed in its message.

39) Released in September 2000, Madonna’s 'Music' album was recorded while she was living in London with husband Guy Ritchie.

The pioneering dance punk sound and Madonna’s cowgirl look helped the album and lead single hit number one on both sides of the Atlantic.

40) Way before Kylie discovered country music, Madonna went there with 'Don’t Tell Me', line-dancing with smoking hot cowboys.

41) In October 2002, Madonna released 'Die Another Day', the theme tune to the Bond film, taking the strings expected of a Bond theme and combining these with her own sound to create a fucked-up electroclash.

The futuristic video resurrected the Good Madonna/Bad Madonna motif of her early career.

42) The following year, Madonna released her 'American Life' album, which featured political lyrics railing against materialism and the American Dream.

It didn’t help that the lead single’s anti-war video had to be pulled days before release when the Iraq War broke out.

43) At the MTV Video Awards in 2003, Madonna re-imagined her performance of 'Like a Virgin', inviting Britney Spears and Christina Aguilera to reprise the song wearing copies of her original costume, before she emerged from a replica wedding cake dressed as a groom.

She then performed Hollywood in a raunchy routine involving her two “brides”, ending by French kissing both of them. it outraged America at the time, but the performance is a daring, gender-queer triumph.

44) Madonna hit the road with her Re-Invention Tour in May 2004. Featuring more hits than The Girlie Show, much more dancing than her recent Drowned World Tour, and films created in collaboration with artist Steven Klein, it was a huge success.

45) In July 2005, Madonna gave a show-stopping performance at the Live 8 concert. She was introduced by Bob Geldof and Birhan Woldu, who’d been the starving child on the TV news report that had inspired Geldof to organise Live Aid 30 years earlier.

Backed by a gospel choir, Madonna sang 'Like a Prayer' holding Birhan’s hand, an image that dominated coverage of the event in the world’s media.

46) When Madonna released the ABBA-sampling 'Hung Up' in October 2005, it was accompanied by one of her most popular ever looks – the pink leotard. The Hi-NRG banger also inspired one of her most memorable dance routines, which she performed to close the Live Earth concert in 2007.

47) After the dark intensity of 'American Life', 'Confessions on a Dance Floor' represented a return to Madonna’s roots and drew influences from Seventies disco. Madonna launched the album with a five-song set at London’s G-A-Y.


48) In 2006 Madonna adopted David Banda from an orphanage in Malawi, one of the poorest countries in the world. The move provoked outrage from sections of the press but she also founded the charity Raising Malawi, which has since built a hospital, orphanage and schools.

49) In 2008 Madonna was inducted to the Rock and Roll Hall of Fame introduced by Justin Timberlake, her partner UK chart-topping single '4 Minutes'.

50) 'Give It 2 Me' was the second single to be released from Madonna’s 'Hard Candy' album.

Written and produced with Pharrell Williams, it’s an upbeat anthem to self-empowerment which sees Madonna addressing the criticism she’d started to receive. ”Don’t stop me now,” she sang, “I can go on and on and on.”


51) On the Sticky and Sweet tour later that year, Madonna performed 'Into the Groove' against a pop-art inspired set that paid tribute to gay artist and close friend Keith Haring, who died of an Aids-related illness in 1990.

52) In February 2012 Madonna performed a four-song set produced by Cirque du Soleil during the Super Bowl half-time show. She made her entrance as Queen Cleopatra being led into the stadium by an army of gladiators, and her appearance attracted 114 million viewers.


53) The second single from her MDNA album was 'Girl Gone Wild', a dancefloor banger about the joys of partying. The black-and-white video saw a vampish Madonna dancing alongside stiletto-heel wearing hunks, who then begin writhing around with each other.

54) At the 2015 Brit Awards, Madonna was due to close the show with an epic performance of her latest single, 'Living For Love'.

But just a few lines into the song she experienced a wardrobe malfunction and, when two dancers tugged at her cape, was dragged off a podium and came crashing to the floor. Social media erupted but Madonna picked herself up, finished the routine.

55) A few months later she performed 'Bitch I’m Madonna' on The Tonight Show with Jimmy Fallon. Emerging from her dressing room, she strutted through the corridors of the studio, trying on costumes, picking up layers of gold jewellery, and corralling various others into action.

The anarchic posse ended up on the show’s set, where Madonna humped the host’s desk.

56) The Rebel Heart tour opened in September 2015, during which she seemed to be having much more fun than previous recent outings.


57) In 2016, Madonna was made Billboard’s Woman of the Year. She made a fiery, funny and brutally honest speech about the inequality she’d experienced as a female entertainer.

“Thank you for acknowledging my ability to continue my career for 34 years,” she said, “in the face of blatant sexism and misogyny and constant bullying and relentless abuse.”


58) That same year, she appeared at the Billboard Music Awards to perform a tribute to her late friend and collaborator, Prince, who’d died just a few weeks before


59) In 2018, the theme of the Met Gala in New York was Heavenly Bodies: Fashion and the Catholic Imagination.

Turning up on the red carpet covered by a black veil, drenched in crosses, and wearing a ball gown designed by Jean Paul Gaultier, Madonna later switched outfits to perform a surprise set backed by a choir of monks

 60) Never one to stay still, Madonna has promised new material to be released soon. But she rarely drops music without causing some kind of stir, prompting many fans to ask what she will do next…