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Posted at 10:39 AM ET, 10/15/2008

Timeline: Madonna's Love Life

By Liz Kelly

Update: It's official -- Madonna and Guy Ritchie announce divorce.

Surprise! Rumor has it that Madonna and husband of eight years Guy Ritchie -- who have been battling rocky relationship rumors for most of 2008 -- plan to divorce by Christmas. While Madge and Guy -- both in the midst of promoting big projects -- may be too busy to reflect on the end of their joint venture, it turns out we've got plenty of time, and space, to devote to overanalyzing their split end. We begin with a look back at Madonna's star-studded (and star-crossed) love life:


Madonna and Jellybean Benitez circa 1985. (Corbis)

1982-ish: Jean-Michel Basquiat. It was the early '80s and the as-yet largely undiscovered Madonna haunted the New York nightclub scene with hipsters, including sometime boyfriend Basquiat, the artist who quickly rose from graffiti artist to Andy Warhol collaborator before dying of a heroin overdose in 1988.

1983: Jellybean Benitez. As Madonna's club career heated up, Benitez lent his hit-making skills to Madge's first album, remixing the songs that landed her on the pop charts: "Everybody," "Borderline," "Lucky Star," "Holiday." Thanks to YouTuber MLVCR58 for posting this compilation of Madonna/Jellybean pix along with the Benitez-produced early Madonna song "Sidewalk Talk."

1985: Sean Penn. The two married soon after meeting and embarked on a mercurial relationship that ended in divorce in the fall of 1989. We have some cherished remembrances from their time together, though. Namely the 1986 box office stinker "Shanghai Surprise" and several pix of Penn trying to keep pushy paps away from M. In 2007, Penn who went on to marry actor Robin Wright, described his marriage to Madonna as "loud": "That’s how I remember it. I don’t recall having a single conversation in four years of marriage."


Madonna and Warren Beatty arrive at the D.C. premiere of 'Dick Tracy' in 1990. (TWP)

1990: Warren Beatty. Madge met the legendary Hollywood lady's man on the set of "Dick Tracy." After a yawn-inducing cameo in her "Truth or Dare" concert documentary film, the two drifted apart.

1991: Tony Ward -- Madonna's relationship with the male model, who appeared in her "Justify My Love" video (NSFW), was brief.

1991: Michael Jackson? Okay, maybe they didn't actually date, but the two -- who People mag at the time described as "Earth's top pop stars" -- did attend the 1991 Academy Awards together.

1991: Jose Canseco. The baseball player now claims that Madonna tried to seduce him, "begged" him to impregnate her and offered the married Canseco financial support if he left his wife.


Madonna and Carlos Leon in 1995. (AP)

1992: Vanilla Ice. (aka Robert Van Winkle) The two dated for about eight months and Van Winkle appeared in some racy photos in Madonna's "Sex" book. In 1994, Van Winkle said of his ex: "She's got a great body for her age (35)."

1994: Dennis Rodman: Youngsters may not remember the flamboyant NBA star, whose tattoos, piercings and tendency to cross dress briefly landed him in the center of the pop culture radar. Post-Madonna, Rodman married (and divorced) Carmen Electra and has recently been spotted in various reality TV projects, including "Celebrity Mole."

1994: Carlos Leon. Madonna's romantic relationship with the personal trainer may have been short, but it did produce a lasting result in the form of daughter Lourdes, now 12.

1999: Guy Ritchie -- The two were reportedly introduced by Sting and his wife and in August 2000 Madonna gave birth to son Rocco. She and Ritchie married on Dec. 22, 2000 and have largely lived in England. Despite rumblings that Ritchie was not fully on board, the couple began controversial adoption proceedings of Malawian child David Banda in 2006.


Madonna and Guy Ritchie greet fans after the baptism of son Rocco in Dec. 2000. (Reuters)

July 2008: A-Rod. Amid growing buzz about Madge's faltering marriage, tabloids resound with news that New York Yankee Alex Rodriguez has been making late-night visits to Madonna's Manhattan pied-a-terre. Although both denied the affair, A-Rod's wife filed for divorce in mid-July. Madonna and Rodriguez, who has reportedly called Madonna his "soulmate," were spotted dining together last week in New York.

Oct. 15, 2008: Word leaks that Madonna and Ritchie plan to announce their impending divorce.

By Liz Kelly  | October 15, 2008; 10:39 AM ET
Categories:  Celebrities  
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Next: Morning Mix: David Duchovny and Tea Leoni Announce Separation

Comments

It's Canseco with an A.

Posted by: As in, "I took A whole lotta steroids." | October 15, 2008 11:00 AM | Report abuse

Wow, I had forgotten the song Sidewalk Talk. Thanks for the memories.

The Sean Penn/Madonna wedding also included allegations of spousal abuse.

Canseco has quite the little steriod induced fantasy life doesn't he?

Posted by: ep | October 15, 2008 11:06 AM | Report abuse

I thought Madonna was into Kabbalah? If so, what's with the baptism pic of son Rocco? And why does his baptism outfit have ears? Just wonderin'

Posted by: hodie | October 15, 2008 11:07 AM | Report abuse

Canseco has quite the little steriod induced fantasy life doesn't he?

Posted by: ep | October 15, 2008 11:06 AM

******************************************

Well, it certainly beats his steroid induced little thing....

Posted by: Dorkus | October 15, 2008 11:08 AM | Report abuse

Well, Hodie. He had accidentally picked up the large, faceless stuffed bear someone had gifted Rocco, instead of his son. You can see the realization of the mistake on Guy's face in this picture.

Posted by: Sully | October 15, 2008 11:13 AM | Report abuse

I remember Warren Beatty saying in "Truth or Dare" that Madonna "doesn't want life to imitate art. She wants it to be art." Keep trying.

(She was pretty good in "Dick Tracy," though, which is more than you can for either "Shanghai Surprise" or "Swept Away." So Warren did give her at least some short-lived acting credibility.)

Post-Guy, she'll club hop with some 20-/30-something ambisexual guy (if he's British, the accent will remain, but I'm thinking she'll move to NYC) and reappear in public in bad clothes with Gwynneth Paltrow.

Speaking of the insoucient one, I wonder if her GOOP newsletter will comment on the breakup? Did anyone here subscribe?

Posted by: td | October 15, 2008 11:13 AM | Report abuse

Guy Ritchie always seems to look blank to me, kinda like Brad Pitt does at times. Change Guy's hair color to red in that photo, and hello Rick Astley!

Posted by: td likes a good *rick roll* | October 15, 2008 11:26 AM | Report abuse

Apparently there is no prenup. Do lawyers in England not believe in protecting their clients' interests? How could you represent someone famous like Madonna or Paul McCartney and NOT insist on a pre-nup?

Although since Guy Ritchie has a life apart from being Mr. Madonna perhaps he will be more reasonable than Heather.

Posted by: ep | October 15, 2008 11:50 AM | Report abuse

Great now I have "Lucky Star" and "Never gonna give you up" playing in my head. I don't think it's going to end anytime soon.

I keep thinking A-Rod is going to wake up one day and wonder what the heck he got himself into. We'll all know when because it will be the scream heard around the world.

td,
I didn't subscribe for fear that I would not be able to unsubscribe from GOOP. I can quit the insouciant one. I'm not sure her site could do that with my email.

Posted by: petal | October 15, 2008 11:52 AM | Report abuse

Clearly this is just the highlights. I doubt Liz has the time or space to catalog every hook-up and encounter Madge has had over the years. I've had broken down used cars with less mileage.

Posted by: yellojkt | October 15, 2008 12:02 PM | Report abuse

Jose Canseco might have a nice little fantasy going there, on the other hand, look at all the former baseball stars he helped to bring down when it turned out a lot of his book was true.

Posted by: jes | October 15, 2008 12:11 PM | Report abuse

Yes, hodie, Rocco was baptised in the Church of Scotland. Considering that, her devotion to Kabbalah and her artistic takes on the Catholicism of her childhood, I have her pegged as a bit of a religious tourist.

And it would appear from this list as something of a romantic tourist, too. Geez, I had forgotten all about Dennis Rodman!

I think she should go for the ultimate bad boy now, like one of those investment banker CEOs who managed a Wall Street firm into the ground.

Posted by: 44west | October 15, 2008 12:16 PM | Report abuse

Native Detroiter Madonna is a I learned a great giver. WHhile at Park West Gallery in Detroit I learned of their Park West Gallery Foundation. Not just about giving art to the masses but also a huge organizer to helping young teens who 'age out' of the foster care system.
Madonna never forgot where she came from and it seems her massive effect on the Detroit and Michigan philanthropy scene go unnoted.
I should add, Park West Gallery is a great philanthropic force to be reckoned with as well. They have donated over 40 million in art work to the 'masses' through colleges and non-profits. Madonna's donations however tower over that and go into the hundreds of millions of dollars.
Please note: I have no history of being a big Madonna fan! I just happened to be at the Park West Gallery in Detroit last week, and put the whole MAdonna is from Dteroit connection together.

Posted by: The Singing Nun | October 15, 2008 12:16 PM | Report abuse

FYI, it appears that Sean and Robin Wright Penn married in 1996 (Wikipedia), in case the year 2007 struck anyone else as odd.

Thanks.

Posted by: NoVa Lady | October 15, 2008 12:18 PM | Report abuse

I'm just assuming that Kabbalah being an offshoot of the Jewish faith that they would also give the kid a bar mitzvah at the proper age. Maybe that would negate that baptism.

All I have to say is now maybe Guy can get back to making good movies cause his output since his marriage to Madge has been, oh let's just say, lacking.

Posted by: Bored @ work | October 15, 2008 12:32 PM | Report abuse

the first pic was not madonna and then boyfriend jellybean it was infact madonna and her then backing dancer !

Posted by: jonie | October 15, 2008 12:33 PM | Report abuse

44west, great terms "religious or romantic tourist".

Vanilla Ice and Dennis Rodman? blech! Guess Guy is too "normal" for her.

Singing Nun, she may remember her humble roots but that doesn't mean she has to let the unwashed masses anywhere near her royal self as her recent opening act somewhere in Scandanavia recently learned.

Posted by: hodie | October 15, 2008 12:36 PM | Report abuse

Does anybody, besides me, remember when BMW got all those big directors to make commercials for them starring Clive Owen? Here is the one done by Guy Ritchie;

http://www.youtube.com/watch?v=LVTVYpZ9ivA

Posted by: Dorkus | October 15, 2008 12:42 PM | Report abuse

"FYI, it appears that Sean and Robin Wright Penn married in 1996 (Wikipedia), in case the year 2007 struck anyone else as odd."
---
It caught me, too, and I had to reread it a couple times before I figured out a comma was missing after Penn.

Annnnnnnnnyyway.
It's been confirmed now that they are splitting and want it done by Christmas (good luck!!!)
Look how good her arms look in that first picture. So healthy and non-sinewey.

Posted by: Em | October 15, 2008 12:48 PM | Report abuse

Looks like there was an official statement from Madonna and guy - they are, in fact, getting a divorce.

Posted by: Betty | October 15, 2008 12:53 PM | Report abuse

Great video, Dorkus! you know I can get fired for watching you tube! I don't think any of those played in our market.

Posted by: hodie | October 15, 2008 12:54 PM | Report abuse

PS. Do you think that is Art imitating life???

Posted by: hodie | October 15, 2008 12:55 PM | Report abuse

Hey Liz! You completed an article about Madonna - a timeline no less - without once referring to her as the "Material Girl". For that, you deserve applause.

Posted by: Potter | October 15, 2008 12:58 PM | Report abuse

Lance Armstrong better move in quick, before Madge decides she wants to be
the Queen Bee and traps Prince William.

Posted by: possum | October 15, 2008 1:09 PM | Report abuse

I was always surprised Madonna spent time with Canseco, given his "steroid induced little thing". She doesn't seem the type to give the time of day to a man whose privates reportedly resemble a gherkin.

Posted by: Californian | October 15, 2008 1:32 PM | Report abuse

test

Posted by: Anonymous | October 15, 2008 1:41 PM | Report abuse

What a diverse list! Madonna must have a lot of energy. I love Basquait's art, I think he is the best of this lot, too bad he is gone.

I do not get the vanilla ice and rodman hook ups, those guys seem odd. oh, well...the saga
continues.

Posted by: Lola | October 15, 2008 1:43 PM | Report abuse

I think, to Madonna, a divorce after eight years of marriage should not be considered a failure. Perhaps it's a sign that at age 50, she doesn't move as fast as she did when she was younger.

Oh...and when did "engineer the public relations" become a euphamism for "work out the financial settlement"?

I blame Heather Mills. But really, I blame Sting and Trudy.

Posted by: MoCoSnarky | October 15, 2008 2:20 PM | Report abuse

I was always surprised Madonna spent time with Canseco, given his "steroid induced little thing". She doesn't seem the type to give the time of day to a man whose privates reportedly resemble a gherkin.

Posted by: Californian | October 15, 2008 1:32 PM

Gherkins, huh? Must be talking about byoolin and the other the geeky, nerdo regulars on this blog.

Posted by: Dumb, pathetic lives | October 15, 2008 2:23 PM | Report abuse

Gherkins, huh? Must be talking about byoolin and the other the geeky, nerdo regulars on this blog.

Posted by: Dumb, pathetic lives | October 15, 2008 2:23 PM

Must also include yourself, afterall you must be a regular to know who the regulars are. ; )

Posted by: hodie | October 15, 2008 2:30 PM | Report abuse

So mMdonna is available?

Remember that rumor about John Mayer getting back with Jennifer Aniston?

Never mind.

And is a gherkin a Nepalese soldier in a British regiment? ;-)

Posted by: Sasquatch salutes the Royal Gherkin Rifles | October 15, 2008 2:44 PM | Report abuse

As I study the timeline of Madonna's love life, I have one question:

WHERE ALL THE WOMEN AT?

Posted by: Sasquatch | October 15, 2008 2:45 PM | Report abuse

"Oh, puh-LEEZE Sasquatch. Madonna and I were just a PR stunt years ago. Nothing happened, so don't get your gherkins in a jar over me."

Posted by: Sandra Bernhard | October 15, 2008 2:51 PM | Report abuse

Madonna is available......

Britney Spears is available.....

Hmmmmmm............

Posted by: Sasquatch plays "As Time Goes By" on his imaginary baby grand | October 15, 2008 2:55 PM | Report abuse

Must also include yourself, afterall you must be a regular to know who the regulars are. ; )

Posted by: hodie | October 15, 2008 2:30 PM

This blog is like a soap opera. The same characters saying the same dumba$s things for YEARS.

Posted by: Dumb, pathetic lives | October 15, 2008 3:01 PM | Report abuse

Madonna? Britney?

Perhaps Mr. Sasquatch would be more interested in something a little more "low-mileage"?

Posted by: byoolin gestures toward this lovely Anne Hathaway: gently used by a wealthy Italian fellow. | October 15, 2008 3:02 PM | Report abuse

Byool, I'd love to take that lightly-used Anne Hathaway model for a test...errr...drive, but Ms. Snatchquatch would not be amused.

What I was thinking in my previous post was matching Madonna with Britney. If a nod is as good as a wink, then what is a kiss as good as?

Posted by: Sasquatch reluctantly leaves the showroom | October 15, 2008 3:07 PM | Report abuse

HEY, everyone!

Let's all get up from our workstations, walk to the nearest portal (door or window), lean out, and yell at the top of our lungs,

I LIVE A DUMB AND PATHETIC LIFE!!!

[pause]

AND I'M A GHERKIN!!!

Posted by: Cheerleader Sasquatch | October 15, 2008 3:10 PM | Report abuse

What I was thinking in my previous post was matching Madonna with Britney. If a nod is as good as a wink, then what is a kiss as good as?

Posted by: Sasquatch reluctantly leaves the showroom | October 15, 2008 3:07 PM

*********

Oooooooohhhhhhhhh.

Madge doesn't seem like the kind of girl who'd retrace her steps. And Britney's in the 'been there, done that' category, isn't she? Or does that VMA thing not count?

Posted by: byoolin lives a dumb and pathetic gherkin life. | October 15, 2008 3:25 PM | Report abuse

Are you all aware that the Swiss Re tower in London is referred to as the Gherkin? Probably because it wouldn't be proper to refer to it as the male body part it most closely resembles.

Posted by: B'More Cat and Gherkin Lover | October 15, 2008 3:30 PM | Report abuse

Sas, I work in the basement of a government building. So, while I very, very much want to go to my door and yell that (did I mention very much?), I think that I would either get fired, or be sent for an EAP (employee assitance program) meaning the guys with the snazy white jacket and butterfly net would show up and treat me to a little involuntary vacation. This would only serve to make my life feel dumber and more pathetic...

However, given that I DO work in the basement of a government building, I can say without hesitation that, "I live a dumb and pathetic life."

Posted by: sunnydaze | October 15, 2008 3:32 PM | Report abuse

Sas,

I can wave pompoms, actually a balled up napkin. The yelling will have to wait until I get home.

Posted by: petal | October 15, 2008 3:42 PM | Report abuse

If a nod is as good as a wink, then what does that make Sarah Palin?

Posted by: hey, Sas! | October 15, 2008 3:55 PM | Report abuse

the Swiss Re Tower, eh? Interesting, that.
I had heard Stanford alumni similarly besmirching the Hoover Tower. After studying images of both, I give the nod to the Swiss Re Tower. The Hoover tower looks more like Janet Jackson's renegade ta-ta is atop the building (a la James Cagney in White Heat)holding off the cops.

Posted by: Sasquatch | October 15, 2008 4:00 PM | Report abuse

Hmmmm....

A nod

A wink

and

Sarah Palin.

Someone dig up the Great Carnac. This is one for him.

Meanwhile, this link to what someone thinks Joe Biden should have said in the V-P debate is R-U-D-E [but funny in a black humor sort of way. No, not *that* kind of black humor.]

http://imagebot.org/debate.jpg

Posted by: Sasquatch needs to quit while he's a head | October 15, 2008 4:04 PM | Report abuse

Another simply FASCINATING day on the Celeb blog......

Posted by: Can't wait for the 'morrow | October 15, 2008 4:07 PM | Report abuse

I truly feel sorry for Madonna. I feel worse for her children. I don't think she knows how to grow old gracefully with class. She wants to be at the center of attention all the time. I feel sorry for her husband who seems like a pretty nice guy. All her money and all her fame isn't going to give her any happiness. At 50 she doesn't have too many options open to her. She could always go on dancing with the Stars like Cloris Leachman.

Posted by: Vienna | October 15, 2008 4:10 PM | Report abuse

Wow, little did I know how much fun we could have with those tiny pickles. :-)

Posted by: Californian | October 15, 2008 4:20 PM | Report abuse

Madonna on DWTS...mmm... There is a ringer and Bruno would get the raunch he loves so much. Don't think it would happen though. DWTS is really for the B listers and has-beens and Madge would not go for that.

Posted by: hodie | October 15, 2008 4:20 PM | Report abuse

Do people think that as Madonna ages, she'll turn into more of a Gloria Swanson or a Mae West (and I don't mean the life-preserver)?

Posted by: Nosy Parker | October 15, 2008 5:16 PM | Report abuse

If a nod is as good as a wink, then what does that make Sarah Palin?

Posted by: hey, Sas! | October 15, 2008 3:55 PM

----
Winkin', blinkin' and odd.

Posted by: MoCoSnarky | October 15, 2008 5:31 PM | Report abuse

You wait - you'll see Madonna with Rodriguez (again) before it's through. Seems interesting that his divorce is final, so now it's Madonna's turn. Just might be real love,you never know!!

Posted by: Cheryl | October 15, 2008 7:12 PM | Report abuse

Madonna dear,
We thee implore,
Go away and sin no more.
If that be too much
We pray,
At any rate,
Please go away.

Posted by: Islamorada Girl | October 15, 2008 9:17 PM | Report abuse

I pray that Guy and Madonna will be able to move on with their lives. I still wish that they will be together aqgain for the sake of the three children but if it's best to live separetely, let it be.

Posted by: Ronald | October 15, 2008 10:14 PM | Report abuse

what a pathetic life?

Posted by: bobby | October 16, 2008 3:40 AM | Report abuse

Madonna felt like a virgin once but I doubt that she's ever been with a virgin. My challenge to her: Date the Pope.

Posted by: larry | October 16, 2008 1:30 PM | Report abuse

By MzEll and Crabby Golightly

I USED TO THINK THAT MADONNA’s move from sexpot to intergalactic hippie after daughter Lourdes was born had finally humanized the diva. I thought that she finally gotten over herself. After all, children are usually good at upending one's vanity.

I thought Guy was a good match. The fake British accent Madge affected after marrying Ritchie and moving to London was ridiculous, but at least she seemed finally stable for her kids. Now that charade seems just another chapter in her book -- or should I say documentary, as she is ever so fond of videotaping herself.

IAt 50, Madonna is really just too old for this current stunt. I'm not sure we care to see her newest metamorphosis if it means sloughing off responsibility for her children. As the chameleon changes colors yet again, it’s her children who have to adjust to the background. Perhaps Madonna doesn’t know herself at the core; more likely, she doesn’t have a core.

Posted by: CrabbyGolightly.com | October 17, 2008 4:54 PM | Report abuse

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