If Hugh Hefner were alive today, sipping cognac in a velvet robe beneath the chandeliers of the Playboy Mansion, he might cast a curious eye on the 2025 landscape—one dominated by algorithms, AI-generated influencers, deepfakes, and synthetic desires. Hefner, the man who pioneered the fusion of sexuality, sophistication, and satire in mid-20th-century America, had an uncanny ability to recognize shifts in culture before they crested. One can imagine him both fascinated and skeptical about artificial intelligence and its profound impact on creativity, relationships, and what it means to be human.

The New Centerfold: From Flesh to Fantasy

“Artificial intelligence is doing what Hollywood never could—making fantasy real,” Hefner might say.

The original Playboy centerfold, introduced in December 1953 with Marilyn Monroe, wasn’t just about nudity. It was about idealism, aspiration, and capturing a zeitgeist. In today’s AI-powered world, tools like Midjourney, DALL·E, and RunwayML are generating hyper-realistic human images. AI models like Aitana Lopez or Lil Miquela have millions of followers despite not being “real.” These AI-generated influencers are flawless—never aging, never scandalous, always algorithmically optimized.

But Hefner likely would caution: “Perfection is boring. Flaws make people irresistible.”

In the golden era of Playboy, it wasn’t about airbrushed symmetry alone—it was about a narrative, an attitude. Marilyn Monroe wasn’t just a bombshell; she was a metaphor for vulnerability wrapped in glamour. Hefner might argue that while AI can replicate form, it struggles with soul—something Playboy always aspired to capture, even in its most provocative content.

Hef’s Take on Today’s “Woke” Culture

If there’s one thing Hefner did with unwavering consistency, it was pushing boundaries. He published interviews with Malcolm X, Martin Luther King Jr., and Steve Jobs. He put Black voices in print when mainstream America recoiled. He defended sexual freedom, civil rights, and expression long before it was cool.

Today’s culture wars—around gender identity, cancel culture, and misinformation—wouldn’t shock him, but he’d likely critique how polarized we’ve become. “Freedom without conversation is just noise,” he might say.

In an AI age where chatbots mimic empathy and deepfakes sow confusion, Hefner would likely advocate for something deeply analog: authentic human connection—preferably over good jazz and a glass of scotch.

The Algorithmic Male Gaze

Playboy was once accused of reinforcing the male gaze. Hefner often defended it as a celebration of feminine beauty and freedom, not objectification. But what would he say about TikTok filters that reshape women’s faces in real time or OnlyFans creators using AI to generate images of themselves at 20 forever?

Hefner might observe: “We’re no longer looking at women. We’re looking at data models of desire.”

AI, in its current form, feeds us back idealized versions of ourselves and others—refined through algorithms built to maximize engagement. To Hefner, this might feel like a loss of something essential. The spark between photographer and muse, the raw flirtation of a first glance, the imperfection of the unedited image—those were Playboy values, even when veiled in artifice.

Yet, he’d also be practical. “If AI can help people explore their fantasies more safely and with more agency, I’m all for it. But we must never let it replace reality.”

A New Kind of Playmate: Companionship in the AI Era

What happens when companionship becomes code?

In Japan and now increasingly in the U.S., millions turn to virtual girlfriends, AI companions, and chatbot lovers. Some are even “marrying” holograms. Would Hefner, the king of the social party, approve of such a shift?

He’d probably smirk. “People have always wanted fantasy. Now they can download it.”

But he’d draw a line. For all his extravagances, Hefner believed in relationships, conversation, shared laughter, and even heartbreak. He might admire the programming sophistication but mourn the decline of intimacy.

“AI can learn your preferences. But it can’t hold your hand when you’re scared. It can simulate love. But it can’t feel it.”

AI in Publishing: Would Hefner Use It?

If Playboy had launched in 2025, would it have used AI writers and AI illustrators? Likely, yes—with a caveat.

Hefner valued innovation. He embraced video, television, digital content early on. He likely would’ve seen generative AI as a tool, not a threat. He might have envisioned Playboy as a multimedia experience powered by AI personalization: articles tailored to the reader’s interests, AI interviews with digital recreations of Einstein or Marilyn Monroe, and centerfolds that adapt to your aesthetic preferences.

But he would have insisted on a human editorial voice—a point of view that means something. “AI can assist, but it can’t provoke. And that’s the editor’s job.”

The Playboy Philosophy in the Age of Machines

In the 1960s, Hefner wrote “The Playboy Philosophy”—a long-running column that outlined his views on freedom, individualism, art, and society. If rewritten today, it might tackle:

• The ethics of synthetic identity
• The monetization of desire via data
• AI’s role in shaping masculinity and femininity
• The illusion of choice in a hyper-curated algorithmic world

Hefner was no technophobe, but he believed technology must always serve the human spirit—not replace it. He might pen a new motto: Fantasy is fleeting. Truth is seductive.

AI, Eroticism, and the Danger of Disconnection

Eroticism, to Hefner, wasn’t just about nudity—it was about anticipation, mystery, and mood. He’d likely criticize the flood of explicit AI-generated content as being too obvious, too available, too boring.

“Eroticism needs mystery,” he might argue. “When everything is exposed, nothing is exciting.”

With AI porn becoming more immersive and indistinguishable from human performance, Hefner might worry we’re losing the capacity for true intimacy. That we’re trading the adventure of connection for the convenience of stimulation.

He might even predict a counterculture movement—“slow sensuality” or “analog arousal”—a return to handwritten love letters, real-life flirtations, and imperfect bodies that feel alive.

AI and Cultural Legacy: Would Hefner Go Digital?

Would Hugh Hefner digitize his legacy?

It’s very possible. One could imagine a Playboy AI Museum, an immersive VR world where you could walk through the mansion, hear conversations with historical guests, browse interactive editions of vintage issues, or even chat with a simulated Hef.

But he’d insist it be done tastefully. With nuance. With wit.

“Legacy,” he might say, “isn’t just about memory—it’s about meaning. It’s not what we preserve, it’s why we preserve it.”

Conclusion: What Hefner Would Leave Us With

In a world of simulated intimacy, deepfakes of Marilyn, and AI chatbots whispering sweet nothings, Hugh Hefner would raise a glass and remind us:

“Technology can enhance fantasy, but it can’t replace romance. Culture is not data. And humanity—our longing, our laughter, our lust—is too wild to ever be fully automated.”

Ultimately, Hefner’s legacy wasn’t about silk pajamas or grotto parties. It was about challenging norms, igniting curiosity, and making people think twice about the boundaries of decency and desire. If he were alive in the AI age, he’d do the same: pose tough questions, spark controversial debates, and publish an interview with ChatGPT right next to a jazz essay, a sex-positive article, and a new vision of what it means to be fully alive in a partially artificial world.