Academy Award for Best Supporting Actress in the context of Zoe Saldaña

Grace Patricia Kelly (November 12, 1929 – September 14, 1982) was an American actress and Princess of Monaco as the wife of Prince Rainier III from their marriage on April 18, 1956, until her death in 1982. Prior to her marriage, she achieved stardom in several significant Hollywood films in the early to mid-1950s. She received an Academy Award and three Golden Globe Awards, and was ranked 13th on the American Film Institute's 25 Greatest Female Stars list.

Kelly was born into a prominent Catholic family in Philadelphia. After graduating from the American Academy of Dramatic Arts in 1949, she began appearing in New York City theatrical productions and television broadcasts. Kelly made her film debut in Fourteen Hours (1951) and gained stardom from her roles in Fred Zinnemann's western film High Noon (1952), and John Ford's adventure-romance Mogambo (1953), the latter of which earned her the Academy Award for Best Supporting Actress nomination. She won the Academy Award for Best Actress for her performance in the drama The Country Girl (1954). Other notable works include the war film The Bridges at Toko-Ri (1954), the romantic comedy High Society (1956), and three Alfred Hitchcock suspense thrillers: Dial M for Murder (1954), Rear Window (1954), and To Catch a Thief (1955).

Dame Olivia Mary de Havilland (/də ˈhævɪlənd/; July 1, 1916 – July 26, 2020) was a British and American actress. The major works of her cinematic career spanned from 1935 to 1988. She appeared in 49 feature films and was one of the leading actresses of her time. Before her death in 2020 at age 104, she was the oldest living and earliest surviving Academy Award winner and was widely considered as being the last surviving major star from the Golden Age of Hollywood cinema. Her younger sister, with whom she had a noted rivalry well documented in the media, was Oscar-winning actress Joan Fontaine.

De Havilland first came to prominence with Errol Flynn as a screen couple in adventure films such as Captain Blood (1935) and The Adventures of Robin Hood (1938). One of her best-known roles is that of Melanie Hamilton in Gone with the Wind (1939), for which she received the first of her five Oscar nominations, the only one for Best Supporting Actress. De Havilland departed from ingénue roles in the 1940s and later distinguished herself for performances in Hold Back the Dawn (1941), To Each His Own (1946), The Snake Pit (1948), and The Heiress (1949), receiving four Best Actress nominations and winning for To Each His Own and The Heiress. She was also successful in work on stage and television. De Havilland lived in Paris from the 1950s and received honors such as the National Medal of the Arts, the Légion d'honneur, and the appointment to Dame Commander of the Order of the British Empire at the age of 101.

The Academy Award for Best Supporting Actor is an award presented annually by the Academy of Motion Picture Arts and Sciences (AMPAS). It has been awarded since the 9th Academy Awards to an actor who has delivered an outstanding performance in a supporting role in a film released that year. The award is traditionally presented by the previous year's Best Supporting Actress winner. However, in recent years, it has shifted towards being presented by previous years' Best Supporting Actor winners instead. In lieu of the traditional Oscar statuette, supporting acting recipients were given plaques up until the 16th Academy Awards, when statuettes were awarded to each category instead.

The Best Supporting Actor award has been presented a total of 89 times, to 80 actors. The first winner was Walter Brennan for his role in Come and Get It (1936). The most recent winner is Kieran Culkin for A Real Pain (2024). The record for most wins is three, held by Brennan–who won every other year within a succession of the first five years. Seven other actors have won twice. Brennan is also tied for receiving the most nominations in the category (with four altogether) along with Jeff Bridges, Robert Duvall, Arthur Kennedy, Jack Nicholson, Al Pacino, Claude Rains, and Mark Ruffalo. For his performance in The Dark Knight (2008), Heath Ledger became the first actor to win posthumously in this category—and second overall. Christopher Plummer is the oldest actor to receive a nomination in any category at age 88, for All the Money in the World (2017).

Helena Bonham Carter (born 26 May 1966) is an English actress. She is known for her portrayals of eccentric women in blockbusters and independent films, particularly period dramas. She rose to prominence by playing Lucy Honeychurch in A Room with a View (1985) and the title character in Lady Jane (1986). Her early period roles saw her typecast as a virginal "English rose", a label with which she was uncomfortable. She is recognized for her unconventional fashion choices and dark aesthetic. For her role as Kate Croy in The Wings of the Dove (1997), Bonham Carter received a nomination for the Academy Award for Best Actress, and for her portrayal of Queen Elizabeth in The King's Speech (2010), she won the BAFTA Award for Best Actress in a Supporting Role, and was nominated for the Academy Award for Best Supporting Actress.

Her other films include Hamlet (1990), Howards End (1992), Mary Shelley's Frankenstein (1994), Mighty Aphrodite (1995), Fight Club (1999), Wallace & Gromit: The Curse of the Were-Rabbit (2005), the Harry Potter series (2007–2011), Great Expectations (2012) as Miss Havisham, Les Misérables (2012), Cinderella (2015), Ocean's 8 (2018), and Enola Holmes (2020). Her collaborations with director Tim Burton include Big Fish (2003), Corpse Bride (2005), Charlie and the Chocolate Factory (2005), Sweeney Todd: The Demon Barber of Fleet Street (2007), Alice in Wonderland and Dark Shadows (2012).

Cold Mountain is a 2003 epic period war drama film written and directed by Anthony Minghella. The film is based on the bestselling 1997 novel by Charles Frazier. It stars Jude Law, Nicole Kidman, and Renée Zellweger with Eileen Atkins, Brendan Gleeson, Kathy Baker, Philip Seymour Hoffman, Natalie Portman, Jack White, Giovanni Ribisi, Donald Sutherland, and Ray Winstone in supporting roles. The film tells the story of a wounded deserter from the Confederate army close to the end of the American Civil War, who journeys home to reunite with the woman he loves. The film was a co-production of companies in Italy, Romania, and the United States.

Cold Mountain was released theatrically on December 25, 2003, by Miramax Films. It emerged a critical and commercial success, grossing over $173 million. It received seven nominations at the 76th Academy Awards, including Best Actor (Law), with Zellweger winning Best Supporting Actress.

Bridesmaids is a 2011 American comedy film directed by Paul Feig from a screenplay by Annie Mumolo and Kristen Wiig. It stars Wiig as a woman who experiences a series of misfortunes after being asked to serve as maid of honor for her best friend, played by Maya Rudolph. The ensemble cast also features Rose Byrne, Wendi McLendon-Covey, Ellie Kemper, Melissa McCarthy and Chris O'Dowd.

Actresses Mumolo and Wiig wrote the screenplay after the latter was cast in Judd Apatow's comedy Knocked Up (2007). Upon its theatrical release in the United States on May 13, 2011, Bridesmaids was a critical and commercial success. It grossed over $306 million worldwide on a $32.5 million budget, and surpassed Knocked Up to become the top-grossing Apatow Productions film to date. At the 84th Academy Awards, McCarthy was nominated for Best Supporting Actress, and Wiig and Mumolo for Best Original Screenplay.

Sideways is a 2004 American comedy-drama directed by Alexander Payne and written by Jim Taylor and Payne. A film adaptation of Rex Pickett's 2004 novel, Sideways follows two men in their forties, Miles Raymond (Paul Giamatti), a depressed teacher and unsuccessful writer, and Jack Cole (Thomas Haden Church), a past-his-prime actor, who take a week-long road trip to Santa Barbara County wine country to celebrate Jack's upcoming wedding. Sandra Oh and Virginia Madsen also star as women they encounter during their trip.

Sideways premiered at the Toronto International Film Festival on September 13, 2004, and was released in the United States on October 22, 2004. It received widespread acclaim from critics and is regarded as one of the greatest films of the 2000s. At the 77th Academy Awards, the film was nominated for Best Picture, Best Director, Best Supporting Actor (Haden Church), Best Supporting Actress (Madsen), and Best Adapted Screenplay, the last of which it won.

Gentleman's Agreement is a 1947 American drama film based on Laura Z. Hobson's best-selling 1947 novel of the same title. The film is about a journalist (played by Gregory Peck) who pretends to be Jewish to research an exposé on the widespread antisemitism in New York City and the affluent communities of New Canaan and Darien, Connecticut. It was nominated for eight Academy Awards and won three: Best Picture, Best Supporting Actress (Celeste Holm), and Best Director (Elia Kazan).

The movie was controversial in its day, as was a similar film on the same subject, Crossfire, which was released the same year (though that film was originally a story about homophobia, later changed to antisemitism).

Psycho is a 1960 American horror film produced and directed by Alfred Hitchcock. The screenplay, written by Joseph Stefano, was based on the 1959 novel of the same name by Robert Bloch. The film stars Anthony Perkins, Janet Leigh, Vera Miles, John Gavin and Martin Balsam. The plot centers on an encounter between on-the-run embezzler Marion Crane (Leigh), shy motel proprietor Norman Bates (Perkins) and his disturbed mother. A private investigator (Balsam), Marion's lover Sam Loomis (Gavin) and her sister Lila (Miles) investigate her disappearance.

Psycho was seen as a departure from Hitchcock's previous film, North by Northwest (1959), as it was filmed on a small budget in black-and-white by the crew of his television series Alfred Hitchcock Presents. Initially, the film divided critics due to its controversial subject matter, but audience interest and outstanding box-office returns prompted a major critical re-evaluation. Psycho was a massive commercial success; from a budget of $806,947 ($6.2 million with 2025 inflation), the film gained $50 million ($384.5 million with 2025 inflation) at the box office, worldwide, not including the money made with rentals. Psycho was nominated for four Academy Awards, including Best Director for Hitchcock and Best Supporting Actress for Leigh.