Pop queen Madonna was desperate for a baby with basketballer Dennis Rodman but her ovulation clashed with his schedules.
Actor Warren Beatty searched her trash for clues to her infidelity and actor Sean Penn fought with her so violently in a hotel room that a table was sent flying.
Madonna lore just got juicier with these revelations from her brother Christopher Ciccone, whose book My Life With My Sister Madonna was published this month.
Ciccone, 47, was her back-up dancer, dresser, artistic director and house decorator from the 1980s to 2003 when their relationship soured. Here are some of his revelations about her many lovers.
Actor Sean Penn, 47
Penn won Ciccone over in a bizarre blood-letting incident: Just before he married Madonna in August 1985, he cut his and Ciccone's thumbs with a knife in his kitchen, pressed them together and said: 'Now we are blood brothers.'
Six years later, after his divorce from Madonna, he met Ciccone at a party. Recalling the incident, he asked Ciccone, who is gay: 'You don't have Aids, do you?'
So much for blood brothers.
Their relationship was tested in 1986 when the couple fought one night while in Hong Kong to film Shanghai Surprise.
Ciccone writes: 'I wake up to the sound of furniture being thrown around in Madonna and Sean's suite next door. He's screaming at her... 'I'm the actor, you're not. You should forget about acting. Stick to singing instead,' Sean screams at her.'
Madonna fled to his room and he slammed the door on the pursuing Penn. 'I wish I weren't his brother-in-law,' he writes.
The couple divorced in 1989. Penn went on to marry actress Robin Wright but they split up last year.
Film-maker Guy Ritchie, 39 (main image)
Ciccone portrays the film director as a homophobe. 'Guy's pride in his own heterosexuality swells noticeably in the presence of a gay man like me,' he writes.
At their first meeting at designer Donatella Versace's New Year's Eve party in Miami in 1999, Ciccone saved a teenage boy, who was dancing intimately with Madonna, from being bashed by Ritchie.
Ritchie later surprised Ciccone by grabbing and bouncing him up and down. In the ensuing tussle, Ciccone shoved him up a wall.
At Madonna's nuptials with Ritchie in Scotland in 2000, Ciccone, peeved at the anti- gay mood at the wedding, ended a toast to the couple by saying: 'And if anybody wants to (make love) to Guy, he'll be in my room later.'
Ritchie continued to irritate Ciccone by banning his decor suggestions for Madonna's Beverly Hills marital home as too 'mincey' and 'twee' - too gay, that is, Ciccone says.
To Ciccone, Madonna's marriage is being held together by her Kabbalah faith. She has a seven-year-old son, Rocco, and a two-year-old adopted Malawian boy, David Banda, with Ritchie.
The Ciccones' sibling Melanie, who stayed in Madonna's London home, told of tension in the house and of a Kabbalah rabbi dropping by to mediate between the Ritchies.
Actor Warren Beatty, 70
Beatty was obsessed with Ciccone's sexuality. He quizzed him on what it was like to be gay when they first met. The same thing happened on their second, third and fourth meetings.
Ciccone was charmed nonetheless. But he did not encourage Madonna when she told him that the legendary ladies' man, then 52, had proposed to her. She was 31 when she got involved with Beatty while working on the 1990 film Dick Tracy (above).
Madonna stalled on the marriage issue and was soon cheating on Beatty with a Latino.
One night, Ciccone saw Beatty in the office of Madonna's house riffling through her trash can - for proof of her infidelity, he claims. 'Warren, operator that he has always been, had the sense to recognise his equal in Madonna. An accomplished philanderer, he has met his match and he knows it,' he writes.
The romance fizzled after 15 months. Beatty married actress Annette Bening in 1992.
Basketballer Dennis Rodman, 47
When Madonna wanted a child in 1994, she and Ciccone thought up a 'Daddy's Chair' where potential fathers with the right credentials could sit.
Madonna fixed on basketballer Rodman as a candidate. She wrangled a magazine interview with him and they went straight to bed after the photo shoot, Rodman claimed later.
But she was frustrated that her ovulation clashed with his NBA schedules. There was no Rodman baby and they split up after a few months together.
Personal trainer Carlos Leon, 42
Madonna had a daughter, Lourdes, in 1996 with personal trainer Carlos Leon. But she regarded him as more than a stud she had cast in the Daddy's Chair, says Ciccone. She was in love with him and wanted their relationship to survive.
But, to her, he behaved like a 'spoilt child' and she doubted if he was intelligent enough to sit in the Daddy's Chair. She subsequently ended the affair by locking him out of her New York flat.
John F. Kennedy Jr, 38
Madonna fancied herself as actress Marilyn Monroe when she became romantically involved with the son of the former US president John F. Kennedy between 1987 and 1988, while still married to Penn.
She boasted to Ciccone: 'I feel like I am repeating Marilyn and the president.'
Monroe was linked to John F. Kennedy before her death in 1962.
Kennedy Jr and his wife Carolyn Bessette died in a plane crash in 1999.
My Life With My Sister Madonna is available at major bookstores at $44.89.