It is the one honor in Hollywood that a star can refuse and receive anyway. When PEOPLE selected Matt Damon as its Sexiest Man Alive in 2007, the actor wrote the editors a letter respectfully explaining why he did not want the title. They named him anyway. What happened next became one of the franchise’s favorite stories, retold by former executive editor Elizabeth Sporkin during the PEOPLE VIP live chat on Thursday, Oct. 22: Damon came around, and thanked the team in a way nobody forgot — a case of red wine for every editor who worked on the issue.
A Refusal, Respectfully Delivered
Sporkin, who joined Editor-in-Chief Charlotte Triggs and moderator Ana Calderone for the chat, said the 55-year-old actor “initially turned down the title when PEOPLE selected him in 2007, even sending the editors a letter explaining, respectfully, why he didn’t want it.” The editors moved forward with the decision regardless. It was not the first time the franchise had improvised its way to a cover: as Triggs recounted in the same conversation, the entire tradition began in 1985 when a photo shoot with Mel Gibson produced pictures too hot to waste and an interview that was, in Triggs’ word, “unusable.” “Somebody suggested, ‘Why don’t you just call him the “Sexiest Man Alive” and just run the pictures?’ And they did that,” she said.
(Harald Krichel / Wikimedia Commons (CC BY-SA 4.0))$75 a Bottle
The Damon story has a second act, and it is pure Damon. “He was so touched,” Sporkin said of the Odyssey star’s reaction once the issue landed. “He sent each editor that worked on the issue a case of red wine.” The detail that made Triggs laugh: “I looked it up. It was $75 a bottle,” Sporkin added. Triggs called it an “elegant touch.” A case of wine for every editor on the issue is not a token gift — it is a cellar’s worth of gratitude, delivered by a man who had tried to decline the crown in writing. PEOPLE’s own joke in telling the story writes itself: how about them apples — or should we say grapes?
In Good Company
The chat placed Damon’s gesture inside a longer history of cover stars shaping their own moments. Sporkin recalled her own staffer-era issue — George Clooney’s, in 1997 — as the franchise grew from a single cover story into an entire issue of different takes on sexiness. She also told the story of the 2010 shoot with Ryan Reynolds on a farm in Atlanta, where the crew defied instructions not to feed a stray dog that was “skin and bones.” “And we fed it, of course,” she said. A publicist adopted the dog, Reynolds handed over his own dog’s crate and leash, and the dog — named Sam, for Sexiest Man Alive — lived about 15 more years in his forever home.
(Beto Pasillas / Wikimedia Commons (CC BY 3.0))And then there is the current standard-bearer. Jonathan Bailey, the 2025 honoree, art-directed his own beach shoot in southern England — styling input, time in the ocean with his dog Benson, and a house-shaped teapot he bought on Amazon himself for a shot of him pouring tea. “He just really knew what he wanted,” Triggs said, adding that she could picture the 38-year-old Bridgerton star working as an art director if he weren’t an actor. Between Damon’s wine, Reynolds’ dog crate and Bailey’s teapot, a theme emerges: the title sticks in people’s memories not for the cover line, but for what the men did when nobody was asking them to pose.
(CezarADA / Wikimedia Commons (CC BY-SA 4.0))The Letter, the Crown and the Cellar
Consider the sequence from Damon’s side. He is selected in 2007 — the editors’ choice, made. He writes back, respectfully, declining: a letter, not a publicist’s statement, explaining why he does not want it. The editors proceed anyway, which could easily have curdled into resentment. Instead, when the issue appeared, Damon was “so touched” that he turned the moment into a thank-you the whole masthead could drink. Each editor who worked on the issue received a case. Not a bottle — a case, at $75 a bottle by Sporkin’s own later research. In an industry where cover subjects routinely send flowers to a single editor, Damon sent a cellar to the entire team that had overruled him.
There is also a quiet symmetry the chat surfaced: the man who said no was honored by a franchise that itself began with an accident — a Mel Gibson shoot in 1985 whose interview could not be used, saved by a headline invented on the spot. Sexiest Man Alive has always advanced by improvisation: an unusable interview becomes a 41-year institution; a polite refusal becomes its most charming acceptance story. Sporkin’s telling — the letter, the decision to proceed, the wine arriving afterward — has the shape of the franchise in miniature.
Why the Story Endures
It also says something about PEOPLE that the story was saved and retold by the very editors who received the wine — Sporkin remembered not just the gift but the price per bottle, nearly twenty years later, which suggests the cases were noticed, appreciated and talked about in the office for a long time.
Nearly two decades on, the Damon anecdote survives because it captures what the franchise sells at its best: sexiness as graciousness. A star who says no, means it politely, and then sends the newsroom a case of $75-a-bottle red wine each has understood the assignment better than anyone. With Triggs teasing this year’s cover star as “epic” and six shoots planned for the new issue, the bar for the next honoree is not just the cover — it is the story the editors will still be telling in 2045.