Madonna's 50 most memorable moments

Jacko at 50: the good, the Bad and the ugly

Madonna turns 50 on Saturday, just days before her Sticky & Sweet tour reaches Britain. Michael Jackson also marks his half-century this month with a new greatest hits collection due, but no sign of his promised comeback album. Two controversial megastars with overlapping careers but very different fortunes: how did it all go so right, and so wrong, for the planet’s most famous pop duo?

1 Suffer childhood hardship

Times Archive, 1985: Madonna's flirt rock phenomenon comes under fire

American feminists accuse the brazen 26-year-old superstar of setting the cause of women back years

• Moving to the music of money

• Madonna: Like a Virgin

Related Links

• Madonna's 50 most memorable moments

• Jacko at 50: the good, Bad and the ugly

• Madonna: A life in 10 songs

Madonna Louise Ciccone and Michael Joseph Jackson were born just 13 days apart in neighbouring US states.

The third of six children, Madonna would later exaggerate the poverty of her middle-class upbringing in the Detroit suburbs. However, the death of her mother from breast cancer clearly took its toll on the five-year-old. The arrival of a stepmother she never accepted was another spur to escape and reinvent herself. Meanwhile in nearby Gary, Indiana, Jackson suffered years of physical and mental abuse at the hands of his stern steelworker father, Joseph. The seventh of nine children, Jackson was pushed into singing and dancing from an early age. He only went public with his family history in a series of tearful interviews in 1993.
Angela’s Ashes rating: Maddy 7/10; Jacko 7/10

2 Reinvent yourself

Madonna has always been the mother of reinvention, starting with her carefully embroidered creation myth as a refugee who arrived in New York with just $35 and a dream. Like Dylan or Bowie, her career has been a series of shape-shifting collaborations and elusive masks: virginal vamp, Marilynesque bombshell, Material Girl, ambisexual dominatrix, spiritual diva, lady of the manor.

Jackson’s reinvention has been more fundamental and problematic, changing the entire shape of his face with nose jobs and other cosmetic tweaks. His skin has also lightened over the years, apparently due to the medical condition vitiligo. Both stars are, in all senses, self-made. But Jackson is ahead by a nose.
Man in the Mirror rating: Maddy 6/10; Jacko 7/10

3 Turn scandal into opportunity

Both Madonna and Jackson have attracted huge controversy, but with very different outcomes. Maddy’s hypersexual image has generated plenty of calculated outrage, titillating with hints of lesbian affairs, bondage and sadomasochism – although it is telling that her 1992 Sex book and Erotica album marked a tipping point, ushering in half a decade of critical and commercial decline. Jackson’s sex scandals have proved far more serious and damaging and have overshadowed his career.

First, he was accused of sexually molesting Jordan Chandler, who withdrew his allegations after a $22 million pay-out in 1994. A decade later, a dramatic high-profile child-sex trial ended in acquittal. But both left Jackson emotionally and financially drained, his reputation badly battered, perhaps irretrievably.

It didn’t help when he was filmed dangling his baby son from a third-floor hotel balcony in 2002. Ironically, in the early 1990s, Jackson asked Madonna to co-write his teasingly titled song In the Closet, but he deemed her lyrics too sexually explicit and dropped them.
No such thing as bad publicity rating: Maddy 7/10; Jacko 0/10

4 Marry another celebrity, however briefly

Pop superstars have long recognised the brand-boosting potential of marrying somebody screamingly incompatible but famous. In 1985 Madonna wed the pugilistic actor Sean Penn, dedicating her 1986 album True Blue to “the coolest guy in the Universe”. Soon afterwards, Penn was charged with domestic assault. Their split was finally legalised in 1989.

When Michael Jackson married Lisa Marie Presley in 1993, he was reeling from sex abuse allegations and prescription-drug addiction. “I wanted to save him,” she later confessed. After several cloying media appearances designed to showcase their healthy, lustful, adult, heterosexual relationship, they divorced.
In sickness and in health rating: Maddy 7/10; Jacko 6/10

5 Ruffle religious feathers

Upsetting the religiously devout is always a good career move. Brought up as a Jehovah’s Witness, Michael Jackson reportedly remains devout, turning to his faith in troubled times. He attracted criticism for his messianic posturing in the video for his 1995 Christmas chart-topper Earth Song but incurred nothing more serious than Jarvis Cocker’s bum-waving excommunication at the 1996 Brit Awards.

By contrast, Madonna has always recognised the headline-grabbing power of religious taboo. She has earned several Vatican condemnations for her saucy stage antics. She also angered Church groups with her 1989 video for Like a Prayer, in which she kisses a statue of a black Jesus back to life, and the mock crucifixion on her 2004 tour. Tellingly, her 2000 wedding to Guy Ritchie was a Church of England affair. Meanwhile, Madge has wholeheartedly embraced the mystic Judaism of the Kabbalah, claiming “it would be less controversial if I joined the Nazi party”. Maybe, but think of all that lovely publicity, sweetie.
Papa Don’t Preach rating: Maddy 8/10; Jacko 3/10

6 Persist with a disastrous film career

Truly dreadful films are the mark of a major crossover popstar brand. Surprisingly, despite his friendships with Hollywood royalty such as Elizabeth Taylor and Steven Spielberg, Michael Jackson’s acting career stalled on the starting line. His clunky Wizard of Oz update The Wiz, his 3-D sci-fi novelty Captain Eo and his vanity project Moonwalker are best forgotten.

Madonna, meanwhile, has amassed more than 20 movie credits, from the credible Desperately Seeking Susan to the middling Evita to the jaw-droppingly awful straight-to-video flop Swept Away. Admittedly the latter may have been a subliminal bid to sabotage the career of her husband Guy Ritchie, because Madge recently moved into feature directing with her lacklustre Brit-com Filth and Wisdom. Her nerve, at least, is impressive. The current state of her marriage to Ritchie is much speculated over.
It’s the films that got smaller rating: Maddy 5/10; Jacko 3/10

7 Fall out with family

Another surefire gauge of a pop star’s importance is a public attack from an estranged relative, which in no way reeks of opportunistic cash-in. In 1993, Michael Jackson’s sister LaToya told a news conference that she believed the rumours about his child molesting were true. She later withdrew the statement, claiming it was made under duress from her former husband. But in general, Jacko’s siblings have rallied around to support him.

At the moment Madonna is facing a full-on nuclear meltdown from her brother Christopher Ciccone in his mud-slinging memoir, Life With My Sister Madonna. Once a dancer and interior designer for his more famous sibling, Ciccone vents years of pent-up resentment over unpaid bills, slights and snubs, blaming Ritchie’s immersion in homophobic Britlad culture for souring their relations. “I gave up my life to help make you the evil queen you are today,” Ciccone tells Madge. “Fifteen years listening to your bitching, egotistical rantings, mediocre talent and a lack of taste that would stun the ages.” Fantastic soap opera.
He Ain’t Heavy, He’s My Brother rating: Maddy 8/10; Jacko 3/10

8 Sue your record label

Both Jackson and Madonna have exchanged lawsuits with their record companies in recent years. It’s a gamble that can backfire badly. Announcing plans to leave Sony shortly before releasing his poor-selling 2001 album Invincible, Jacko later claimed that the label failed to promote the record in a calculated bid to deplete his finances and force him to sell Sony his publishing stake in Northern Songs, the Beatles back catalogue. Bizarrely, in 2002, he protested in an open-top bus outside Sony HQ, branding the chief executive, Tommy Mottola, “devilish” and “racist”.

Two years later Madonna and her sub-label Maverick sued Warner Music Group, claiming the corporation had lost Maverick millions of dollars through financial mismanagement. Both record companies counter-sued. The disputes were resolved, but Jackson terminated his Sony contract for an ultimately fruitless joint venture with a Bahraini prince. Madonna is still signed to Warners, but will soon leave for a new recording deal with Live Nation, worth $120 million.
Bite the hand that feeds rating: Maddy 7/10; Jacko 3/10

9 Take care of business

In sheer numbers, both Jackson and Madonna are phenomenal success stories. His credits include the bestselling album of all time, Thriller (1982), with global sales somewhere close to 100 million. His royalty rate is notoriously high, his fortune estimated in billions, and his overall record sales of 750 million dwarf Maddy’s 200 million. And yet she may yet prove the smarter long-term investor. With her new Live Nation deal and estimated net worth of $400 million, she is the most successful female pop artist yet, recently surpassing Elvis Presley in the US Top Ten singles league.

Meanwhile, Jackson’s million-dollar shopping sprees and legal bills have forced him to sell off a majority chunk of his publishing business. Now living off massive bank loans, he recently came close to losing his Neverland ranch in California. But he is reportedly preparing a comeback album to be released on his own label. And possibly delivered by unicorn.
Credit crunch rating: Maddy 8/10; Jacko 4/10

10 Move to Britain

Unlikely as it sounds, settling in Wiltshire and adopting that comical cod-English accent has coincided with a sustained upturn in Madonna’s critical and commercial success. Her recent run of chart-topping albums have made Mrs Ritchie the female artist with the most UK No 1 singles to date. Yes, OK, as long as we overlook that terrible rap about feeling super-duper in a Mini Cooper. So can Jacko take a leaf out of Maddy’s book? Bizarrely, Jackson’s brother Tito has bought a family hideaway near Barnstaple in Devon, and Michael has visited twice.
Dick Van Dyke rating: Maddy 8/10; Jacko 4/10

Overall rating
Maddy 71/100; Jacko 40/100

Despite Jackson being a superior singer, better dancer and bigger seller, his career is a shambles while Madonna goes from strength to strength. Her toughness, commercial sense and smart command of pop trends have served her well. Jackson is damaged goods, but remains a genius with a loyal global following. If he can muster just one more great album, this could be the mother of all comebacks.

Now read the books...

The explosive new book, 'Life with my sister Madonna,' by Christopher Ciccone.

Michael Jackson, 'The Magic and the Madness,' by J.Randy Taraborrelli.

Explore Music

• Festivals

• CD Reviews

• Live Reviews

• Classical

Editor's choice

• U2 at Nou Camp Stadium, Barcelona
• The 50 Best Movie Villains
• The 15 golden rules of theatre etiquette