Alyssa Arce titties over Playgirl magazine advertised a “Sleep with Donald Trump” contest in 1990… An Ode to a Nightmare: The Time a Magazine Tried to Give Away Donald Trump Like a Cursed Toaster Oven

Playgirl Magazine warning about Donald Trump’s black flags since 1990 ✅️💯

In 1990, Playgirl magazine advertised a “Sleep with Donald Trump” contest.

Bubba’s Sexist Ads Blowout Series…

First ad: Cigarettes fits for King Trump…

An Ode to a Nightmare: The Time a Magazine Tried to Give Away Donald Trump Like a Cursed Toaster Oven

Gather ‘round, children of a less-grim timeline, and let me tell you a tale not of heroism, but of horror. A story so psychologically scarring that it makes the plot of The Human Centipede look like a heartwarming buddy comedy. We must travel back to the halcyon days of 1990, when hair was big, greed was good, and Playgirl magazine committed an act of gross public endangerment.

The offending artifact is this full-page ad, a monument to poor life choices:-

A sexist vintage ad from the 1970s, promoting some fancy two-tone men’s shoes and more ads…

This ad for pants depicted a woman as a tiger-skin rug, boasting: ‘After one look at his Mr Leggs slacks, she was ready to have him walk all over her’.

Let us dissect this cultural crime against humanity.

The “Prize”: A Night of Unparalleled Luxury (and Psychological Trauma)

The advertisement screams, in a font usually reserved for used car dealerships, “YOU’LL SLEEP WITH DONALD TRUMP!” Not “you might,” or “you could,” but the definitive, terrifying “YOU’LL.” It was a threat masquerading as a prize.

What did “sleep with” entail? According to the fine print, the “winner” would receive:

A “sensuous night” in his “luxurious Trump Tower apartment.”
The “opportunity” to “unwind with Donald after one of his typically hectic days.”

Let’s be fucking clear. This wasn’t a prize; it was a hostage situation with a mint on the pillow. The winner wasn’t going to be swept off their feet; they were going to be a prop in a one-man play titled “Look At How Successful I Am, Witness My Gold-Plated Faucets.” The “sensuous night” would likely involve a four-hour monologue about the inferior deal-making skills of the building’s condo board, the unparalleled beauty of his own name in 24-karat gold, and a detailed breakdown of why his steak was the best steak, cooked well-done with ketchup.

There were even ads that promoted sugary drinks for toddlers, asking: ‘How soon is too soon? Not soon enough’.

Light up Mom! This ad claimed ‘you need never feel over-smoked’. Perhaps they hadn’t heard of lung cancer.

The “hectic day” he’d be unwinding from? Probably consisted of:

Calling a journalist a “dog.”
Firing a subordinate on a whim.
Staring at his own reflection for 45 minutes to ensure it hadn’t betrayed him.

This wasn’t a romantic getaway. It was an unpaid, unlicensed therapy session where you were the therapist, and your patient was a human panic attack in a Brioni suit.

“Show her it’s a man’s world”. Van Heusen Man’s World ties: “For men only! … brand new man-talking, power-packed patterns that tell her it’s a man’s world… and make her so happy it is.” 1951.

Want to have some fun? How about some domestic violence before heading out with your buddies?

The Impact on Society: The Day Hope Died

What was the societal cost of this ad? We can calculate it in the collective shudder that still ripples through the zeitgeist.

The Devaluation of the Word “Luxury”: Before this, “luxury” implied taste, elegance, and quiet wealth. After this ad, it became synonymous with gaudy, gold-plated excess designed to overcompensate for a cavernous void within. The entire interior design industry suffered a setback from which it has never fully recovered.
The Betrayal of Feminism: Playgirl was, in theory, meant to empower women by presenting the male form as an object of desire. This ad betrayed that mission spectacularly. It wasn’t offering a fantasy; it was offering a lesson in leveraged buyouts. It told an entire generation of women that their ultimate reward was not personal achievement or genuine connection, but becoming a temporary accessory to a man who likely saw them as a new acquisition. The resentment this caused is immeasurable.
The Normalization of the Clown-Car-as-President: This contest, and the countless other shameless self-promotions of the era, helped to sand down the public’s edges of discernment. It made the bizarre seem commercial and the outrageous seem like just another publicity stunt. We were being conditioned, one grotesque headline at a time, to stop being shocked. We learned to laugh at the buffoonery, not realizing we were laughing all the way to a very dark, very real destination.

Acme, 1963: The most important quality in coffee is how much it will please your man.

Advertisement for STDs.

As one brave (and likely traumatized) source from the time noted, the whole affair was a masterclass in Trump’s worldview: “Everything is transactional, everything is promotional, and every human interaction is a potential segment for a talk show that only he is watching.” Source: The Washington Post

The Chilling Conclusion

So, let us pour one out for the unknown soul who “won” this contest. We don’t know who they are, and they have likely spent the last three decades in a witness protection program for the psyche, trying to forget the feel of crushed velvet and the sound of their own dreams dying to the tune of “You’re Fired.”

The “Sleep with Donald Trump” contest was more than just a weird 90s artifact. It was a canary in the coal mine of American culture, a flashing red sign that screamed: “ABANDON ALL TASTE, YE WHO ENTER HERE.” We didn’t listen. We just turned the page, and now we’re all living in the goddamn centerfold.

“A cigar brings out the caveman in you.There’s a man-size feeling of power in smoking a cigar.” 1959.

“Where there’s a man… there’s a Marlboro”. This vintage magazine advertisement from 1970 also included this absurd line: “The cigarette designed for men that women like.”