2. Diane Keaton (1946–2025) – Annie Hall, Something’s Gotta Give

With her quirky style and Oscar-winning performance in Annie Hall, Diane Keaton carved a space for herself as Hollywood’s beloved eccentric. Even in her 70s, she kept leading romantic comedies and redefining what aging looks like on screen, with Book Club and its sequel among her later hits, and her fashion sense stayed as enviable as ever. Keaton died in October 2025 at 79.