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Greatest Oscar Winners

Updated on February 17, 2013
The prestigious Academy Awards ceremony
The prestigious Academy Awards ceremony | Source

Winning an Academy Award is one of the highest accolades that can be earned by those in the film industry, so it's no surprise that very few actors have managed to achieve this honour more than once in the acting category. However, the following actors have, whether deserved or not, had their skills solidified numerous times by the Academy, rendering them some of the best remembered on-screen talents and providing them with the highest number of Oscars in the profession.

Katharine Hepburn
Katharine Hepburn | Source


Who better to start off this list than Katharine Hepburn, who's lengthy career won her the following Academy Awards:


  • 1933 – Morning Glory (actress in a leading role): When a relatively inexperienced theatre actress undergoes a series of auditions and acting lessons, eventually gaining a small role in an upcoming Broadway production, she finds herself working alongside a star whose sudden departure as a result of unmet financial demands provides the young would-be actor with a ticket to success.


  • 1967 – Guess Who’s Coming to Dinner? (actress in a leading role): When a young, confident and independent woman brings home her African-American fiancé, everyone involved must grapple with their prejudices and reservations in this exploration of love, civil rights, and inter-racial marriage.


  • 1968 – The Lion in Winter (actress in a leading role): This fictionalised account of Henry II explores his inability to decide which of his three sons ought to inherit the throne, as he endeavours to keep power within his grasp, and the consequential plotting of both them and his estranged wife, Eleanor of Aquitaine, to force him to commit to a decision.


  • 1981 – On Golden Pond (actress in a leading role): A daughter visits her parents at the cottage where they spend each summer for the first time in years, temporarily leaving her fiancé’s son in their care. Upon her return to the cottage she is irritated to discover that the boy has bonded with her father to a degree that she was never able to achieve. It is through the child that she eventually manages to form a connection with her father.

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Walter Brennan
Walter Brennan | Source

Walter Brennan also proved his worth to the Academy with the following performances:


  • 1936 – Come and Get it (actor in a supporting role): When a lumberjack dismisses his chance at happiness in order to marry into a position of wealth and power, he later finds himself falling for his first love’s daughter and grappling with his son for her affections.


  • 1938 – Kentucky (actor in a supporting role): A young keeper of horses meets a man who offers to help train a prize horse for the Derby. She accepts, unaware of his position in the family that has been feuding with hers since the days of the Civil War.


  • 1940 – The Westerner (actor in a supporting role): A self-appointed, highly corrupt judge in Texas befriends a man charged for horse theft when he delays his death sentence in order to obtain a lock of his favourite actress’ hair, to which the accused claims to have access.

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Ingrid Bergman
Ingrid Bergman | Source

Ingrid Bergman also refused to be outshone, beating out all for her performances in:


  • 1944 – Gaslight (actress in a leading role): A woman who witnessed her aunt’s murder as a child moves into the latter’s house years later with her husband. There she falls victim to a number of bizarre events, all of which appear to prove, and that convince her of, her insanity and instability.


  • 1956 – Anastasia (actress in a leading role): When an astute Russian businessman eager to claim the ten million pounds left by the Tsar attempts to cast a mysterious woman in the role of the Grand Duchess Anastasia, she proves to be so convincing that it becomes impossible to determine whether she is or is not who she claims to be.


  • 1974 – Murder on the Orient Express (actress in a supporting role): The murder of an American businessman aboard the Orient Express is investigated by detective Hercule Poirot, who is almost certain that the murderer is one of the passengers on the train.

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Jack Nicholson
Jack Nicholson | Source

Jumping into a slightly more recent era, we of course have Jack Nicholson, whose talents in the following films have forced him to make the acceptance speech thrice:


  • 1975 – One Flew Over the Cuckoo’s Nest (actor in a leading role): Based on the 1962 novel of the same name, this film tells the story of the oppression and humiliation suffered by a group of patients in a mental institution at the hands of the tyrannous Nurse Ratched, who ultimately becomes locked in a battle of wits with the confident patient Randle McMurphy.


  • 1983 – Terms of Endearment (actor in a supporting role): Chronicling the love/hate relationship between a mother and daughter as they hunt for love and acceptance, the pair is forced to individually face life’s challenges and is ultimately strengthened by them.


  • 1997 – As Good As it Gets (actor in a leading role): Exploring the relationship between a misanthropist novelist suffering from Obsessive-Compulsive Disorder, the sole waitress in his daily restaurant who can actually tolerate him, and his gay, artistic neighbour, this film investigates the metaphorical journey towards self-discovery and realisation through a literal journey to Baltimore that binds the fates of the trio.

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Meryl Streep
Meryl Streep | Source

It would be impossible to forget one of the best loved and most deeply cherished actors of the age, Meryl Streep, whose Oscar winning performances comprise her roles in:


  • 1979 – Kramer Vs. Kramer (actress in a supporting role): Depicting the intense custody battle for their son following their divorce, Ted and Joanna Kramer are forced to navigate issues pertaining to family and devotion in this film that explores shifting gender roles and development towards caring, competent parenting.


  • 1982 – Sophie’s Choice (actress in a leading role): Set in 1947, this shattering drama follows Stingo’s (a novelist from the American South) meeting with the Polish immigrant, Sophie, and her lover, Nathan. A series of flashbacks reveal her haunting past in the Auschwitz Concentration Camp and the infinite cruelty of the ‘choice’ that she was forced to make there.


  • 2011 – The Iron Lady (actress in a leading role): This film explores the controversial and influential career of the only female Prime Minister of the UK, in office from 1979-1990, and her use of both firm, inflexible politics and implementation of policies that have come to be known as Thatcherism.

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