Annette Bening, the guest on this episode of The Hollywood Reporter’s Awards Chatter podcast, is one of the most talented and admired actresses of her generation. Vanity Fair has called her “a leading lady from the old school,” who “epitomizes the wit and glamour of modern Hollywood.” The Los Angeles Times has said she “brings to mind such Golden Age actresses as Bette Davis, Claudette Colbert and Barbara Stanwyck — sassy, ready-for-anything heroines a half-step ahead of their man.”

Over the course of some 35 years in the business, Bening has given standout performances in films like 1990’s The Grifters, 1991’s Bugsy, 1995’s The American President, 1999’s American Beauty, 2004’s Being Julia, 2010’s The Kids Are All Right, 2016’s 20th Century Women and 2017’s Film Stars Don’t Die in Liverpool. Most recently, she starred in 2023’s Nyad, in which she portrays Diana Nyad, a woman who spent years of her life trying to become the first person to swim the 110 miles from Cuba to Florida without the aid of a shark cage.

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For Nyad, Bening was nominated for a best drama actress Golden Globe Award; is nominated for a best actress SAG Award nomination; and on Tuesday morning received a best actress Oscar nomination, her fifth one. She has yet to win.

During a conversation at the Los Angeles offices of PMC, the 65-year-old reflected on her transition from stage actress to screen actress with The Grifters, for which she received her first Oscar nom, followed a year later by Bugsy, on which she met and co-starred opposite her soon-to-be-husband and frequent collaborator Warren Beatty. She opened up about the two films in which she did some of her best work and for which she probably came closest to winning an Oscar — American Beauty and Being Julia (coincidentally she came up short both times to the same person, Hilary Swank). The five-time nominee also touched on the underestimated and somewhat discarded middle-aged women she played in 20th Century Women, Film Stars Don’t Die in Liverpool and Nyad, plus much more.

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