Woody Allen, at 90, Stands Firm on Friendship with Jeffrey Epstein Amid New Estate Photos
New York, December 2025 — In an era when public figures routinely issue carefully worded apologies or strategic silences upon the resurfacing of ties to Jeffrey Epstein, Woody Allen has chosen a markedly different path: unapologetic candor bordering on indifference.
Just months after celebrating his 90th birthday, the Oscar-winning director has once again addressed his long-standing acquaintance with the late convicted sex offender, describing him in recent interviews as “charming and personable” — a characterization that has drawn fresh scrutiny following the release of intimate photographs from Epstein’s estate.
The images, made public by Democrats on the House Oversight Committee in mid-December as part of an ongoing probe into the Justice Department’s handling of the Epstein case, depict Allen and Epstein in relaxed, personal settings over multiple years. One widely circulated photo captures the two men seated across from each other at a table, coffee cups and water glasses scattered between them, engaged in what appears to be lingering post-meal conversation. An unidentified woman is the only other figure present. Other images show Epstein on the set of one of Allen’s films and the director aboard Epstein’s private jet — the aircraft infamously nicknamed the “Lolita Express.”
Allen, who turned 90 in late 2025, has not shied away from discussing the relationship. In a September interview with The Sunday Times, conducted shortly before his milestone birthday, he recounted attending dinner parties at Epstein’s Upper East Side townhouse — located near his own residence — and meeting figures such as Prince Andrew there. “He couldn’t have been nicer,” Allen said of Epstein. “We never, ever, saw Jeffrey with underage girls. He always had a girlfriend but never an underage girlfriend.”
The remarks, delivered with the filmmaker’s signature deadpan delivery, stand in sharp contrast to the mea culpas offered by others linked to Epstein, including Bill Gates and former British Prime Minister Tony Blair, who have expressed regret over their associations. Allen’s refusal to express remorse has reignited debate about the boundaries of social proximity to a man convicted in 2008 of procuring a minor for prostitution and later facing federal sex-trafficking charges before his death in 2019.
Critics argue that the newly released photos — part of a trove exceeding 95,000 images from Epstein’s estate — reveal a level of intimacy that goes beyond occasional social encounters. The images suggest repeated, comfortable interactions in private environments, raising questions about how much knowledge — or willful blindness — accompanied such closeness.
Yet Allen’s defenders, a shrinking but vocal group, point to the absence of any evidence linking him to Epstein’s criminal activities. No allegations of wrongdoing have been made against the director in connection with Epstein, and the photos themselves show no illegal conduct. Allen has long maintained that his interactions were limited to dinners and intellectual conversation, consistent with his self-described preference for “always interesting” company.
The timing of the photo release coincides with a broader political push to fully disclose Epstein-related materials before mandated deadlines. For Allen, the development arrives amid a personally eventful period: the publication of his first novel, What’s With Baum?, the loss of longtime collaborator Diane Keaton, and a rare spate of media appearances.
At 90, Allen remains one of Hollywood’s most polarizing figures, his career shadowed by decades-old allegations of sexual abuse from his adopted daughter Dylan Farrow — claims he has consistently denied. His comments on Epstein fit into a pattern of defiance against public judgment, a stance that has both sustained his small but dedicated following and alienated much of the industry.
As the Epstein files continue to trickle into public view, the photographs serve as a stark reminder of the financier’s ability to cultivate relationships with the elite. For Woody Allen, however, they appear to change little. In the quiet glow of his nonagenarian years, he has looked straight into the camera and offered no apology — only the same assessment he has held for years: Jeffrey Epstein was charming, personable, and worthy of his dinner invitations.
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