Madonna’s 50 most memorable moments

Times Online, August 2008, Special

1983: After making a name for herself in the clubs of New York, Madonna secured a record deal and released her self-titled debut album. Although it took a whole year for the album to reach the US top ten, the dancefloor classic Holiday was a massive hit on both sides of the Atlantic.

2. Madonna-mania with Like A Virgin

1984: Madonna proved she wasn’t a one hit wonder with the release of follow up album Like a Virgin which sold 12 million copies worldwide. Both the album and title song made it to number one in the US charts, while Material Girl was also a big hit.

3. On-screen debut in Crazy For You

1985: Madonna played a club singer in coming of age movie Vision Quest with Matthew Modine. The film was re-released outside the US as Crazy for You following the success of Madonna’s title song.

4. Film stardom in Desperately Seeking Susan

1985: Although Rosanna Arquette was the star of 1985 film Desperately Seeking Susan, Madonna stole the show as gutsy New York drifter Susan, one of her most memorable screen roles. The film features Into the Groove, still one of her all-time club classics, and a dance sequence shot at Danceteria, the club that helped launch her career.

5. First marriage, to Sean Penn

1985: After a passionate romance with actor Sean Penn, the pair married at the home of millionaire developer Kurt Unger. The ceremony was drowned out by the din of helicopters overhead as journalists attempted to capture it on film. The marriage was shortlived and after a number of separations, the couple finally divorced in September 1989.

6. Playboy nude photo scandal

1985: In the late 70s, young and unknown, Madonna posed for a series of nude black and white photographs. When they made their way onto the pages of Playboy and Penthouse in 1985, the Queen of Pop showed an uncharacteristic shyness, attempting, and failing, to block publication.

7. Preaching to the Pope

1986: Her third album, True Blue, was another hit, earning her four top five singles. Among them was Papa Don’t Preach, the story of a pregnant teenager who chooses to keep her baby. Madonna, who was raised a Catholic, dedicated the song to the Pope.

8. First of the film flops

1986: Madonna takes to the screen again in the underwhelming Shanghai Surprise, made by husband Sean Pean, the first in a long line of film flops. In her next film, Who’s That Girl in 1987 she played Nikki Finn, a feisty ex-con who spices up life for Griffin Dunn’s uptight New York lawyer. Loved by teenage girls, dismissed by everyone else, it launched two more hit songs, Causing a Commotion and Who’s that Girl.

9. Who’s courting controversy?

1987: Madonna’s first world concert tour, The Who’s That Girl World Tour took her across America, Europe and Japan. A record-breaking financial success, it also earned her plaudits for its daring, theatricality, and raunchiness. Pope John Paul, however, was offended and urged fans not to attend her Italian appearances.

10. Lesbian love?

1988: Towards the end of the 80s Madonna was spending a lot of time with lesbian comedienne Sandra Bernhard sparking much press speculation that the two were having an affair.

11. Pepsi and the Pope

1989: The video for Like A Prayer, title single of the forthcoming album, featured stigmata and burning crosses and attracted more vitriol from the Vatican. Madonna, and the song, were to star in a Pepsi commercial, but in the wake of the controversy the advert was pulled after only a handful of showings.

12. Gangsters moll

1990: The next move in her bid to become a great Hollywood star saw Madonna play Breathless Mahoney in the film adaptation of Dick Tracy. As well as putting her mark on the film, and earning her praise from the critics, the film sparked an affair with her co-star and director, Warren Beatty

13. Vogue dance craze

1990: Her eighth US number-one single and video Vogue, took inspiration for – and brought to public attention – the New York gay club craze, Vogueing, in which dancers imitate their favourite Hollywood stars and cover models.

14. Masturbation controversy

1990: Her world tour Blond Ambition, during which she simulated masturbation to Like a Virgin, incited another boycott call from the Pope and the threat of arrest in Toronto. It also produced the iconic image of her in Jean-Paul Gaultier’s conical bra outfit and cemented her reputation as one of pop’s greatest theatrical acts.

15. MTV bondage ban

1990: More controversy with the video for Justify My Love, released with her greatest hits compilation The Immaculate Collection, which featured scenes of sadomasochism, bondage and same-sex kissing. It was all too much for MTV which banned it from the station.

16. Bedroom expose In Bed with Madonna

1991: Fans were given a rare insight into life on the road with Madonna in the documentary In Bed with Madonna (released as Truth or Dare in the US). As well as a behind the scenes look at the controversy surrounding the Blond Ambition tour in 1990, it showed her leading pre-show prayers and enjoying bedroom antics with her dance troupe.

17. Hot for Ice

1992: After their eight month affair, rapper Vanilla Ice (aka Robert Van Winkle) dished the dirt to USA Today: “She would call me at strange hours, ‘Are you in bed with another girl?’ At 6 in the morning, man, I’m like, ‘I’m (expletive) sleeping all alone. What the (expletive)? Why do you keep doing this?'” But is she a sexual animal? “Nah, she’s like every normal girl, man. She’s very sexy, she’s hot, she’s romantic. She’s got a great body for her age (35).”

18. Entertainment empire

1992: Madonna cemented her fortune with a multi-million pound deal with Time Warner. Under a seven year agreement, the singer was advanced $60 million to found her own entertainment company, Maverick, which brought together her music and film interests. Compared by Madonna at the time to the formation of the German Bauhaus, the partnership unravelled in a legal wrangle over mismanagement and improper accounting.

19. Soft porn coffee table book Sex

1992: In her first foray into publishing (but not dirty pictures) Madonna, created an alter-ego Mistress Dita to produce Sex – a coffee-table glossy of risque soft core photographs. The book, promoted by her fifth album Erotica, sold 500,000 copies in the US and was launched at New York City’s Industria Studio where Madonna dressed as Little Bo Peep with a stuffed toy lamb.

20. Puerto Rican protest

1993: Though it failed to live up to Blond Ambition, the 1993 Girlie Show World Tour was another heady mix of provocation and outrage, described by the singer as “a mixture of a rock concert, a fashion show, a circus performance, a cabaret act and a burlesque show”. Puerto Rico was the main focus of protest after she rubbed the Puerto Rican flag between her legs on stage, while in Isreal, due to be her first appearance there, Orthodox Jews protested to cancel.

21. Bedtime Secrets

1994: Her next album Bedtime Stories hit out at the press from her treatment over the many sex controversies and intrusions into her private life. It included her 35th hit Secret, which marked a move back to her R&B roots, and another record-breaking title, making her at the time the most successful artist in UK chart history.

22. Under Siege

1995: She attracted the attention of stalker Roger Hoskins. When the 39 year old invaded her estate in the Hollywood Hills, Los Angeles, he was shot twice as police arrested him.

23. First child Lourdes

1996: Madonna became a mother with the birth of Lourdes Maria Ciccone Leon aka Lola, daughter of fitness instructor Carlos Leon, who she met in Central Park.

24. The Gong for Evita

1996: It might not have been the Oscar she was hoping for, but a rare moment of recognition for Madonna’s acting came with a Golden Globe for her role as Eva Peron in the 1996 film Evita. The film had smashed West End box office records in its first weekend, with Madonna’s single Don’t Cry For Me Argentina shooting straight to No 3 in the UK charts. “Evita is the first movie big enough to contain me,” she said somewhat immodestly at the time.

25. Ray of Light

1998: Although her seventh album, inspired by JG Ballard’s novel The Drowned, took her longer to record than any previous, it failed to outdo them on sales. It did though win her three Grammy Awards including Best Pop Vocal Album and Best Dance Recording.

26. Love again with Guy Ritchie

1999: When Madonna was introduced to Guy Ritchie by Sting and Trudi Styler it was the start of true love, both with the Lock Stock and Two Smoking Barrels film director and with an English aristocratic lifestyle. The couple’s first child – Madonna’s second – Rocco was born in August 2000. And the world came to know her by Ritchie’s new nickname, Madge.

27. The second celebrity wedding

2000: The couple married at the end of the year at an exclusive ceremony at Skibo Castle in the Scottish Highlands. Although the press, and even guests’ cameras, were banned, one journalist had been hiding behind the pipe organ for three days. By the time he was discovered he had passed out.

28. Internet leaks: and Ali G

2000: Madonna was burnt by new download technologies when her album Music was leaked onto the internet months ahead of release. The album included hits What it Feels Like for a Girl and a cover of American Pie. A classic video starred Ali G star Sacha Baron Cohen.

29. Breaking records

2000: As the Noughties dawned, Madonna went down in history as the best-selling female rock artist of the 20th century.

30. Drowned World Tour

2001: Music promoted her Drowned World Tour which continued her reputation for incredible live performance. The show employed 100 tons of equipment, two Boeing 747 jumbo jets (to fly in the equipment), eight trucks (to take the equipment from venue to venue) and 88 travelling production staff.

31. Bond Girl in Die Another Day

2002: Her theme to the James Bond film Die Another Day divided the critics, earning her nominations for both a Golden Globe and a Golden Raspberry. She also clinched an acting role in the film, playing Pierce Brosnan’s fencing instructor Verity.

32. Sinking not swimming: another bad movie

2002: After a series of terrible flops she starred in Swept Away, directed by husband Guy Richie, panned by the critics who described it as “disastrous”, “a shipwreck” and not to be mistaken for an actual movie. Madonna plays a rich American who makes life miserable for a sailor on her luxury yacht, only to find herself shipwrecked on an island with him. Plans for a UK theatrical release were abandoned and the film went straight to video.

33. That lesbian kiss with Britney

2003: It was a field day for the tabloids when Madonna kissed Britney Spears and Christine Aguillera while performing song Hollywood from latest album American Life at the MTV Video Music Awards.

34. The English Rose

2003: She launched the first in a series of children’s books, The English Roses. Inspired by Kabbalah, the wistful morality tale was trashed by the critics.

35. All-time great according to Rolling Stone

2004: Rolling Stone ranked her number 36 on its list of the “100 Greatest Artists of All Time”.

36. Re-invention

2004: And another blockbuster success with her Re-Invention World Tour of the USA, Canada and Europe, which became the highest-grossing tour of 2004, earning $125 million.

37. Trespassers will be prosecuted

2004: Madonna, now frequently spotted in tweeds carrying a shotgun, settled into her new role as a member of the English landed gentry, winning a fight to stop walkers crossing her £9million estate. She continues to attracts the wrath of the animal welfare lobby as she develops her Ashcombe House Estate on the Wilthshire/Dorset border into one of the country’s premier game sites.

38. Cult follower

2005: A long time member of Kabbalah, Madonna bought a £1.6 million home for the London branch of the Jewish cult. Under her spiritual name Esther, she has recruited a clutch of fellow stars, including Demi Moore and Lindsay Lohan.

39. Confessions of a Democrat

2005: Madonna bagged another superlative with her Confessions tour – the highest grossing concert tour by a female artist. Based on material from the album Confessions on a Dance Floor, the controversy this time wasn’t just down to the sexual content but her political attack on president George Bush. Performing the song I Love New York, she replaced the original lyrics “just go to Texas, isn’t that where they golf?” with “just go to Texas and suck George Bush’s dick!”

40. The fans turn after Revolver

2005: Madonna and Guy are booed by disappointed fans outside the premiere of Richie’s latest flop Revolver, upset at being ignored by the couple. Critics dismissed the film as even worse than Swept Away.

41. (Not so) cuddly namesake

2006: She became the only star to have a species of water bear tick named after her, Echiniscus madonnae.

42. Third child David Banda

2006: She joined the ranks of celebrities adopting foreign babies, bringing David Banda back from Malawi amidst a storm of controversy over whether she had acted legally. The adoption was finalised earlier this year.

43. Cruelty to animals

2006: After being spotted wearing a Chinchilla fur coat leaving a London restaurant she became a target for People for the Ethical Treatment of Animals (PETA).

44. Hitting the high street with H&M

2007: Her clothing line for Hennes & Mauritz, co-designed with H&M design chief Margareta van den Bosch, launched around the world. The collection included a leather trench coat and sequined shift dresses and helped the Swedish fashion retailer buck the current high-street gloom with a boost in sales.

45. Hall of Fame induction

2008: She was inducted into the US Rock and Roll Hall of Fame for musicians whose first commercial releases were at least 25 years ago.

46. Directorial debut

2008: Her first attempt at directing with Filth and Wisdom was slammed by the critics for “clunkingly awful acting” and “stagey scening”. Times chief film critic James Christopher said her new career “got off to a surprisingly auspicious start without exactly convincing anyone that she should give up her old job.”

47. Still hot with JT

2008: She may be getting older but she can still play the leading lady to a fit young buck as she proved this year when she teamed up with Justin Timberlake with single 4 Minutes from the album Hard Candy.

48. Marriage on the rocks

2008: As Madonna approaches her 50th birthday, rumours continue that her marriage is on the rocks. Ritchie has reportedly left Kabbalah sparking further rumours of an imminent split.

49. Trouble with the law?

2008: More trouble on the horizon as Madonna and Ritchie’s Mayfair pub The Punch Bowl faces closure because of complaints of over-charging. Non-regular patrons of their pub were supposedly charged more money for a pint, a breach of the law.

50. Rags to riches

2008: For all her troubles, Madonna is now one of the world’s richest women. After signing a new deal with the Live Nation entertainment group, she is now worth £300m and stands at 270th place in the Sunday Times Rich List.