Being a gay icon, part of the reason for Madonna’s status as such also stems from her flavor for overly butch men (so “butch” to the point of it almost being a form of drag, replete with leather). Sean Penn was an early example of such taste, when she married him at the peak of his “bad boy” reputation in the 80s. A decade that was still highly heteronormative and favoring of the “conventional” definition of masculinity. Hence, having an ex-(fake) cowboy as the president. Penn fit quite neatly into these definitions, particularly off-screen, when his volatile temper was allowed to truly flourish after coalescing with the most famous woman in the world.
Those who don’t remember ought to be reminded that Madonna met Sean Penn on the set of the Mary Lambert-directed “Material Girl” video in January of 1985. His cameo at what was then called Ren-Mar Studios stemmed from Penn’s personal assistant, Meegan Lee Ochs, inviting him to stop by (likely at Madonna’s encouragement). Seeing her in her Marilyn drag, maybe he fancied himself the roguish Joe DiMaggio type. Because from that moment forward, the romance was decidedly whirlwind, with the two marrying in August of the same year. But Penn’s “bad boy” charisma didn’t seem so charming anymore when Madonna became guilty by association—with the press branding them as the “Poison Penns” as a result of his tempestuous public persona. Which may not have been that much of a persona based on a police report filed by Madonna in December of 1988 after an “alleged” incident during which he broke into their home, tied her to a chair and tortured her physically and emotionally with lines to the effect of, “I’ll cut your hair” and “I own you, lock, stock and barrel.” An eerie choice of words considering Madonna’s second (and probably last) husband, Guy Ritchie (another faux butch sort with homophobic tendencies), would have a film called Lock, Stock and Two Smoking Barrels that would ultimately bring them together (with Madonna’s Maverick label releasing the soundtrack).
After being held captive for roughly nine hours, Madonna fled to the Malibu police station, where Lieutenant Bill McSweeney would note, “I hardly recognized her as Madonna. She was weeping, her lip was bleeding and she had obviously been struck.” Apparently, his bloodlust for photographers had been momentarily transferred to his own wife, soon to be ex. And sure, those who would continue to give Penn the benefit of the doubt would probably say that his explosivity was all part of his 1980s “growing pains.” Which he eventually “grew out of.” Not so. Penn’s history of violence in general and with paparazzi in particular continued to rear its ugly head even in the twenty-first century after he was charged in 2010 for kicking a paparazzo and breaking his camera. It also seemed, as the 2010s progressed, that he traded in offending people with violence by preferring to offend with words. Like his illustrious “green card” comment at the 2015 Oscars. After presenting Alejandro González Iñárritu (for whom Penn starred in 21 Grams) with the award for Best Picture, Penn “quipped,” “Who gave this son of a bitch his green card?”
González Iñárritu was quick to defend Penn, considered a friend, among the backlash, just as Madonna was after Lee Daniels accused Penn of being a wife beater. This in the wake of Penn being mentioned by Daniels in a 2015 interview, during which he stated, “[Terrence Howard] ain’t done nothing different than Marlon Brando or Sean Penn, and all of a sudden he’s some fuckin’ demon. That’s a sign of the time, of race, of where we are right now in America.” It didn’t take long for Penn to declare “defamation of character” with a lawsuit (eventually dropped), during which Madonna was tapped to provide the following statement: “Sean never struck me, ‘tied me up’ or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless and false.” Eh. For whatever reason, Madonna and Penn need to have their whitewashed version of how they want the world to presently view their overtly toxic relationship. One that, to this day, many still wish had been able to continue. But someone like Penn being with someone like Madonna patently does not compute. She being a feminist and he being, well, a misogynistic, homophobic pig of the “good ol’ boys” philosophy (and no, that could not be masked by him playing Harvey Milk).
This much was confirmed yet again in a fresh interview from Penn for The Independent. After having already told another publication, “I am in the club that believes that men in American culture have become wildly feminized. I don’t think that being a brute or having insensitivity or disrespect for women is anything to do with masculinity, or ever did. But I don’t think that to be fair to women, we should become them,” Penn went even further for The Independent. Thus, he added, “I think that men have, in my view, become quite feminized. I have these very strong women in my life who do not take masculinity as a sign of oppression toward them. There are a lot of, I think, cowardly genes that lead to people surrendering their jeans and putting on a skirt.” Hmm, tell that to a Scotsman. Or Pete Davidson (who wore one to the 2021 Met Gala). Or Russell Westbrook (who wore one to New York Fashion Week, also in 2021). And then there is the (somewhat queerbaiting) resurgence of dress-wearing by Harry Styles. Not to mention the longer history of straight men like Kurt Cobain and Brad Pitt wearing dresses as well. In short, Penn ought to know from his own industry that there is no “cowardly gene” that makes a man choose to wear whatever the fuck he wants, so much as a firm sense of identity and confidence (e.g. David Bowie—incidentally, one of Madonna’s biggest heroes). Whereas Penn comes off as totally insecure, as though he doth protest too much the way he did toward Lee Daniels about being abusive, or the way Benedict Cumberbatch’s character, Phil Burbank, does in The Power of the Dog. Clinging to old school visions of “masculinity”—already a false and damaging construct to begin with. And, accordingly, it’s no coincidence that he plays an anachronistic dinosaur of an actor modeled after William Holden in Licorice Pizza.
To make matters more humiliating, Sean’s daughter, Dylan, was sitting next to him when he said this (as the two were promoting Flag Day for its UK release date—will Guy Ritchie see it?). Her reaction, per The Independent, was to turn “quiet, staring into space.” What else can you do when you realize your father might have brain damage? As many other white males of his generation also seem to—something Penn addressed when he commented, “I’m a little frustrated with the world. I’m glad I’m old and won’t be having to deal with where this stuff is going.” It’s tantamount to most boomers throwing up a peace sign on the ills—namely, climate change—that they helped make impossible to unravel, instead opting to leave it to younger generations to “figure out” as they look on with a “well, I’ll be dead anyway so it doesn’t really affect me” attitude.
This, too, is another marked contrast between Penn and Madonna, the latter of whom has stated she’ll probably outlive us all (probably even Cher). And with no intention of capitulating to stereotypes of what “aging” should look like, Madonna comes across as far more concerned with the collective’s future than her ex-husband—and that includes more than a concern for the environment, but also shattering outmoded notions of “gender norms.” Particularly the one that “decrees” women can’t be sexual or sexy past forty (if that). Indeed, Madonna even sang on 2019’s Madame X, “Not everyone is comin’ to the future/Not everyone is learnin’ from the past.” One such person is clearly Penn, who would prefer to cling to his antiquated mid-twentieth century notions of “dick-swinging.”
Thandiwe Newton said it best when she railed, “Dude what are you saying? Like for real? You’re a jibbering fool…you used to be sexy but now you’re just tragic. In front of your daughter!? That poor little mite. Thank God her Mum’s so dope [though Madonna might tend to agree if “Thief of Hearts” is an indication]. Please stop ruining the brilliance of Licorice Pizza with this nonsense.”
So yeah, it’s really bad when you’re a more embarrassing ex than Vanilla Ice or Dennis Rodman (who, by the way, is very fond of dresses and overall “feminine” flamboyance when it comes to fashion).
