The world was still mourning the sudden loss of Diane Keaton—gone at 79 from pneumonia in October 2025—when Woody Allen, her longtime collaborator and former muse, finally broke his silence in a rare interview that sent shockwaves through Hollywood. In the wake of her death, the 90-year-old director stunned many by describing Jeffrey Epstein, the convicted sex offender at the center of one of the darkest scandals in modern history, as “charming and personable”—a man who “couldn’t have been nicer” during their dinners together.T

In the weeks following Diane Keaton’s quiet passing in late December 2025, the entertainment world braced for tributes from her longtime collaborator and friend, Woody Allen. The director, now 90 and long absent from public life, had remained almost entirely silent since his own controversies began dominating headlines decades ago. Then, on January 9, 2026, he granted a rare, hour-long telephone interview to a small French film journal, speaking for the first time in years about personal loss, legacy, and—unexpectedly—Jeffrey Epstein.

The most incendiary moment came when the interviewer asked whether Allen had ever crossed paths with Epstein during the financier’s years of cultivating Hollywood and academic elites. Allen paused, then answered with unsettling calm: “I met Jeffrey a few times. He was charming, personable, very quick-witted. He had that kind of magnetism that draws people in. It’s a shame what happened.”

The words landed like a grenade. Within hours, clips of the audio spread across social media, reigniting every dormant question about Hollywood’s long, tangled relationship with Epstein. Allen’s casual characterization of a man later convicted of sex trafficking—and accused by dozens of victims of orchestrating a vast network of abuse—struck many as tone-deaf at best, complicit at worst. Survivors’ advocates pointed out that Epstein’s charm was precisely the weapon he used to groom and silence. Others noted the grim timing: Virginia Giuffre’s posthumous memoir, still dominating headlines, had just named several entertainment figures who allegedly frequented Epstein’s circles.

Allen offered no apology, no clarification. He shifted quickly to memories of Keaton—her laughter on the set of Annie Hall, her courage in facing illness—before ending the call. The interview closed with his familiar, soft chuckle: “Life is strange, isn’t it?”

For many, the strangeness now feels unbearable. In eulogizing one icon, Woody Allen inadvertently exhumed the darkest questions about another era’s blind spots. Hollywood, already fractured by recent reckonings, must once again confront whether charm ever excused complicity—and whether silence, even in grief, remains a luxury the powerful can still afford.