Anyone But A-Rod: An Eight-Pack Of Madonna’s Past Loves, And The Chances They’ll See Another Ray Of Light

Posted at 9:00 AM Oct 20, 2008

By Kevin Smith

Thanks to the news of her impending divorce from Guy Ritchie, the American people have taken a quick moment from observing the destruction of the global economy to plead with Madonna from the bottom of their precious hearts: “For the love of God, not A-Rod!” It seems that the Material Girl has been in England for far too long and doesn’t realize what a gigantic douche Alex Rodriguez, her rumored lover, happens to be. So to help Ms. Ciccone along in her newly single dating life, below is a small sample of her past loves for renewed consideration (even including Mr. Ritchie), with a likelihood of reconciliation (ranked in order of who we’d ideally enjoy seeing her reconnected with). Because even though Madonna’s vagina has had more visitors than the Grand Canyon over the last few decades, there is still time for her to find that true blue love, and it may just come from a familiar face. Or at least penis.

8. Prior Madge-Meat: Jean-Michel Basquiat

Stage Of Her Career: Struggling Bohemian/Shining Star
Their Immaculate Conception
Before they were famous—Madonna for her charming habit of not wearing panties and Basquiat for creating some of the most terrifying paintings this side of the river Styx—they were just two weird art kids living and loving on the same decrepit New York streets.
The Day The Music Died
In the end, the dirty squalor could not contain either of these two visionaries. Madonna took what she learned, marginalized it for Middle America and started the process of turning all tweens into pint-sized whores. Basquiat, on the other hand, was discovered by world-renowned freak Andy Warhol and invited to countless art shows with free cheese and bad wine.
Chances Of Reconciliation: 2 Percent
Like all great artists, Jean-Michel developed a lovely little heroin addiction and subsequently died in 1988. His untimely demise does not completely count out a renewal of their once-fiery passion. Madonna has been known to change her image frequently, so perhaps a necrophilia phase is in the cards. We can only hope.

7. Prior Madge-Meat: Carlos Leon

Stages Of Her Career: Eva Peron Wannabe/Desperate For A Baby
Their Immaculate Conception
The father of Madonna’s first child, Lourdes, Leon was nothing more than sperm with a hot tanned body, a donor who could dance. She wanted to have the best-looking child possible baby and found a young, fit, ethnic provider. Not to mention Mr. Leon also falls into one of Madonna’s favorite fetishes, the minority athlete. Although, in fairness, he seems to be the high water mark of that group.
The Day The Music Died
This seemed to be one of those "Meet superstar, provide seed, become famous for doing so and move along" type of relationships. While Carlos and Madonna likely make for an enjoyable time at PTA meetings, at that point time, she still possessed strong, wandering urges and playing house wasn’t one of them yet.
Chances Of Reconciliation: Fifty Percent
By all accounts, Leon seems like a good fella. He has kept his trap shut regarding his time with Madonna and has an active relationship with Lourdes. Does that seem like lofty praise for basically not screwing up and seeing a rich kid a few times a year? Sure. But compared to some of the schlock on this list, it’s near a miracle. So if she’s going to backslide, Leon is still vigorous and seems sensible enough to put up with the pure lunacy that must come along with being Mr. Madonna.

6. Prior Madge-Meat: Guy Ritchie

Stage Of Her Career: Ray Of Light/Ugly British Nanny
Their Immaculate Conception
Another reason to dislike Sting (if you needed any others) is that he was the matchmaker between these two. She had recently entered her 40s and wanted to settle down, and who could be better than a charming British bloke who makes low-budget crime flicks? Probably any other male in the United Kingdom, since the guy’s a one-trick pony in love with Cockney rhyming slang and inane double crosses captured with choppy editing.
The Day The Music Died
Seemed only a matter of time, given Guy has been responsible for turning our wild deity of depravity into a proper English lady with a fake posh accent and a children’s book called The English Roses. Does Mr. Ritchie have no shame?
Chances Of Reconciliation: Fifteen Percent
Guy and Madonna had their fun, but that bridge is done burned. She’s a phoenix rising from the ashes of this failed relationship. With the help of Kabbalah and an ego that knows no limits, she will trap another innocent young man and mold him.

5. Prior Madge-Meat: Sean Penn

Stage Of Her Career: Material Girl/Bigger Than Jesus
Their Immaculate Conception
A love that burned too bright to contain. This relationship lasted for the better part of the mid-to-late ’80s, at a time when Madonna was the hottest thing in the world and Sean Penn was the older brother of the fat guy from Footloose.
The Day The Music Died
The apparent reasons behind their split were that Sean was a psychotic thug who got his jollies off of beating the living crap out of paparazzi and that Madonna was far too famous to pal around with Jeff Spicoli.
Chances Of Reconciliation: 10 Percent
Penn has recently gotten back together with his wife, Robin Wright Penn (better known as Buttercup from The Princess Bride and Jenny from Forrest Gump. Now, Madonna is a sex goddess and all, but does Gloria from Shanghai Surprise hold up against Buttercup and Jenny? All Sean has to do is consult IMDB and realize he has made the right choice.

4. Prior Madge-Meat: Warren Beatty

Stage Of Her Career: Like A Prayer Vixen/Dick Tracy Dame
Their Immaculate Conception
At the start of their relationship, Madonna was a sprite 30 years young and Beatty was clocking in at a nearly ancient 51. Juxtaposed against the younger men she’d lusted for prior to (and afterwards), Beatty represented a father figure, but he was also a serious ladies man who could definitely compare bed posts with anyone. You name a famous scarlet from the ’60s through 80’s and Warren has laid them down gently.
The Day The Music Died
While Beatty was the male Madonna for the prior generation, no man, not even a legendary swordsman like Warren, could keep pace with Madonna at her peak. It’s honestly surprising that the man’s dick didn’t fall off.
Chances of reconciliation: 33 Percent
Now that Madge is coming back to America, can’t you just picture them meeting at the new Jack Nicholson film (“Old man acts crazy and then realizes his mortality. Part two.”), hitting it off and grabbing a quickie at the after party? Sure, it will most likely involve more lube than a Fire Island wedding, but mature folks have needs as well.

3. Prior Madge-Meat: Jose Canseco

Stage Of Her Career: Vanilla Ice’s Sloppy Seconds
Their Immaculate Conception
Soon after she ended her fling with Vanilla Ice, Madonna was back trolling for more trash. Enter Jose Canseco. In 1991, Canseco was one of the best baseball players in the world, a former Most Valuable Player for his astonishing talent of crushing a tiny white orb, sprinting 90 feet on dirt and bouncing balls in play off his noggin. A Bash Brother with Mark McGwire for his muscular proficiency and also for his bashing needles filled with steroids into friends’ asses. How could Madonna not have turned on SportsCenter and told one of her minions, “He must be mine!”
The Day The Music Died
According to Canseco, Madonna wanted him to father her child because of his Cuban background and athletic prowess. Supposedly, Jose denied her advances since he was still married and found her intimidating. A far more likely story is that Madonna saw him without a shirt on and promptly got sick from the sight of his rancid back acne.
Chances Of Reconciliation: 1 Percent
Maybe if Madonna mistakes Jose for his twin brother Ozzie.

2. Prior Madge-Meat: Dennis Rodman

Stage Of Her Career: Body Of Evidence/Slowly Losing Her Mind
Their Immaculate Conception
Still on her quest to have someone put a baby inside of her, Madonna’s eyes turned away from the baseball diamond in 1994 and to the hard court of basketball, and more specifically its clown prince, Dennis Rodman. Madge even referred to him as the Madonna of the NBA, given his notoriety for bizarre hair colors, cross dressing and crotch kicking. He was the wild spirit that was right up Madonna’s alley, and filling up her alley is just what she wanted him for.
The Day The Music Died
The romance quickly fizzled when the stork kept fleeing in the opposite direction of Madonna’s womb, and these two kooks went their separate ways.
Chances Of Reconciliation: 25 Percent
Rodman is currently married, but given his reputation, a new dalliance between he and Madonna is not out of the question. They are kindred spirits, after all, egomaniacs who believe the world is their circus and that they are the ringmasters.

1. Prior Madge-Meat: Vanilla Ice

Stage Of Her Career: Erotica/Clueless About Men
Their Immaculate Conception
A desperate cry for help? We, the listening public, apparently weren’t the only people that were fooled by Robert Van Winkle’s charms. Poor Madonna just wanted a hardcore rapper to please her and take provocative pictures with.
The Day The Music Died
Turns out that Vanilla was even more of a corporate creation than her. They dated for an inexplicable eight months before Madonna woke up one morning and realized, “Holy shit! I let Vanilla Ice do what to me last night?”
Chances of reconciliation: 0 Percent
Madonna would rather fuck Basquiat’s rotting corpse.

Suggestions For Innocent, Young, Future Madge-Meat
How about Wilmer Valderrama or Frankie Delgado? Yes, we’re referring to Fez from That ’70s Show and Brodie’s sidekick from The Hills. Why not? They’re both young Latino gentlemen and are already pretty much man-whores. Really, anyone will do as long as she’s staying away from A-Rod, who’s so void of human depth that it would only be a matter of time before she became as empty and evil as the Yankee third baseman.

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