Back in 2007, Maxim magazine put out one of the nastiest “features” ever disguised as humour: the “5 Unsexiest Women Alive.” Their picks? Sarah Jessica Parker, Amy Winehouse, Sandra Oh, Madonna, and Britney Spears.
Aside from thinking it’s clever to create a list of unsexy women, what was truly disturbing was the reasons WHY!
At first glance, the whole thing reads like mid-2000s lad-mag banter. It’s cheap, low-effort, and vaguely misogynistic content, but as you read it further the bitter reality hits: men weren’t judging these women on how they looked. They were judging them on their pain. Their age. Their complexity. Their refusal to exist as perfect, glossy fantasy objects.
This wasn’t about “sexiness.” It was about punishing women for being human.
Sarah Jessica Parker topped the list at number 1, the “least sexy woman alive.” The magazine said she was the “least sexy woman in a group of very unsexy women” that ironically starred in a show with the word “sex” in the title.’
Amy Winehouse was number 2 on the list. While she was visibly drowning under addiction, pressure, and the brutality of fame, Maxim described her as having “hemorrhaging translucent skin,” a “rat’s nest mane,” and “lashes like surgically attached bats.”
They didn’t see a woman spiralling. They saw a woman struggling as ‘unsexy’.
Britney Spears made the list, and she was mocked for having “two kids, two ex-husbands, a slight weight gain” and losing the ability to perform. Let that sit with you for a moment, she was deemed ‘unsexy’ because she had children, was divorced, was struggling and therefore couldn’t perform choreography to the best of her ability.
Everything they listed? Life happening. A hard life. A woman experiencing a public breakdown. A woman experiencing trauma, motherhood, pressure, exploitation. And Maxim decided to frame it as: “ew, look how unsexy she is now”.
Sandra Oh. At the height of her career, with her amazing performance in Grey’s Anatomy, the magazine listed Sandra Oh at No. 3 for her “cold bedside manner and boyish figure”. Because even in the midst of a woman doing her job, acting as a doctor in a medical drama, she must find a way to be sexy to male viewers.
Madonna made it to number 4 on the list for her “self-righteous bellyaching”, and her “rapid post-nuptial deterioration” - a grotesque phrase that suggests her worth declined after marriage.
In every one of these cases, sexiness wasn’t really being judged by looks. It was about how complicated a woman appeared to be. Maxim basically published: “Trauma makes women ugly.” The irony is throughout pop culture we’ve seen troubled male stars painted as complex, poetic, tortured souls.
I recently posted on @90smilk Instagram about the list of men labelled sexy by People’s magazine throughout the 80s, 90s and 2000s. Over the years, we’ve seen winners like:
• Richard Gere
• Harrison Ford
• George Clooney
Men with wrinkles, grey hair, frown lines, life experience, marriages, divorces, complicated pasts. These men are ‘sexy’. We’re expected to swoon as we look past their imperfections. Richard Gere literally became more desirable once he got older. He was also crowned sexy after his divorce, a grace not extended to Britney after her divorce. Same with nearly every man crowned “Sexiest Man Alive.” Men are allowed to have ‘unfavourable’ features, they’re allowed to age, they’re allowed to have trauma. Trauma gives them depth. Women’s trauma makes them “unsexy.” Men get called “silver fox.” Women get called “deteriorating.” One magazine celebrates men for living. Another punishes women for the same thing.
Maxim reaffirmed a rule: A woman is only worthy of desire if she is untouched by age, by life, by struggle, by pain.
The women on that list weren’t unsexy, they were just inconvenient for men.





Oh man magazines really existed to keep therapists in business for decades! They did a number on us.
that was painful to read!! it just reminded me how fucked up our society actually is..you did a great job, bring this topic to the table tho!