Olivia de Havilland has had a long history at the Oscars.  She received 5 Oscar nominations and was awarded the Best Actress Oscar twice. Additionally, she has presented at the Oscars, including most recently ,in 2003, at the 75th Annual Academy Awards.  Ms. De Havilland is a current member of the Academy and is eligible to cast votes for the Academy Awards. 

Olivia de Havilland as Melanie Hamilton Wilkes
"Gone With the Wind"
1939

Olivia de Havilland won the role of Melanie Wilkes in Gone With the Wind in 1939.  She gave a phenomenal performance and truly made the role her own.  She and Hattie McDaniel were both nominated for Best Supporting Actress in 1939 for their performances.  Ms. McDaniel edged out Olivia de Havilland for the Oscar.  It was widely reported that Olivia cried at the ceremony for not receiving the award but later acknowledged how wonderful it was that Hattie McDaniel had won the award and that she had been there to witness the event. 

Oscar Night 1940!  The 12th annual Academy Awards were held at the Coconut Grove of the Ambassador Hotel on Thursday, February 29, 1940.  Olivia was present that night for her Oscar nominated performance of Melanie Wilkes.  Laurence Olivier was seen in many photos from the night with Olivia de Havilland because his date, Vivien Leigh, was essentially taken by Gone With the Wind producer, David O. Selznick. 

Photo above: Vivien Leigh, Laurence Olivier, and Olivia de Havilland at the 12th Academy Awards.

Olivia de Havilland was nominated for Best Actress in 1941 for her performance as Emmy Brown in Hold Back the Dawn.  The film also featured Charles Boyer and Paulette Goddard.  The New York Times film review stated," Olivia de Havilland plays the school teacher as a woman with romantic fancies whose honesty and pride are her own—and the film's—chief support. Incidentally, she is excellent."
 
Olivia lost the Oscar that year to her sister Joan Fontaine who won for Suspicion. 

Olivia de Havilland as Emmy Brown
"Hold Back the Dawn"
1941

Olivia de Havilland as Josephine Norris
"To Each His Own"
1946

Olivia de Havilland was nominated and won the Oscar for her role as Josephine Norris in To Each His Own.  In the film, Olivia's character falls in love with a young WWI soldier who is killed.  She is left alone to raise their child and decides to give the child up for adoption and pursue a career in cosmetics.  Later, she runs into the her now adult son while in London.  Mother and son are ultimately brought together. 

"Josephine Norris is a refreshingly modern and sensible woman, and one of the reasons that To Each His Own succeeds so well. Of even greater importance is the performance of the actress portraying her.  Olivia de Havilland's Oscar was well deserved, even in a year that saw stiff competition from Rosiland Russell and Celia Johnson." 
- Craig Butler, All Movie Guide

This was Olivia de Havilland's first film after an enforced two year absence while she was engaged in a lawsuit with Warner Brothers over her highly restrictive contract. 

The 19th Annual Academy Awards were held on March 13, 1946 at the Shrine Auditorium and were hosted by Jack Benny.  It was at this ceremony that Olivia set the record for the most people thanked in an Oscar acceptance speech.  Olivia is noted as having thanked 27 people in her acceptance speech!

Above Photos:  Olivia de Havilland with presenter Ray Milland at the 1947 Academy Awards

To Each His Own Awards:
Academy Award Winner: Best Actress - Olivia de Havilland

Academy Award Nominee: Best Writing Original Story - Charles Brackett

Olivia de Havilland was nominated for Best Actress for her 1948 performance in The Snake Pit.  This was one of her finest performances on screen and one which she has remarked has given her the most pride as an actress.  In the film, Olivia plays the role of Virginia Stuart Cunningham who finds herself in a mental institution in the 1940s with no understanding of why she is there.  The climax of the film occurs when Olivia's character finds herself in "The Snake Pit," the lowest block of the mental institution where the most severely disturbed patients are found jibbering incoherently and aimlessely roaming about!

"The film's representation of Virginia Cunningham and her troubles may seem elementary by today's standards, and the worries about her ability to remain a good wife may feel archaically sexist. But Anatole Litvak's grim portrait of the mental hospital and its residents remain strong and startling, and Olivia de Havilland's Oscar-nominated portrayal of Virginia was a bravely unglamorous choice that still holds up as her best performance."
 - Mark Deming, All Movie Guide

Olivia de Havilland as Virginia Cunningham
"The Snake Pit"
1948

The Snake Pit Awards:
Academy Award Nominee: Best Actress - Olivia de Havilland
Academy Award Nominee: Best Director - Anatole Litvak
Academy Award Nominee: Best Music, Scoring of a Dramatic or Comedy Picture - Alfred Newman
Academy Award Nominee: Best Picture
Academy Award Nominee: Best Writing Screenplay - Frank Partos and Millen Brand

Olivia de Havilland won her second Best Actress Oscar for "The Heiress" in 1949.  In the film, Olivia plays the role of Catherine Sloper, a plain woman who lives with her father after her mother died while giving birth to her.  Her father often reminds her of all the things her mother was and that she is not.  Catherine inherited a great deal of money after her mother passed away and she will inherit twice the amount at her father's passing.  So, when a poor but handsome and well-bred man, Morris Townsend, begins to court Catherine, her father becomes suspicious that he is after her money.

TV Guide said of Olivia's performance, "This was one of de Havilland's greatest roles...and her transformation from docile emotional victim to rational, resolved adult is a masterpiece of acting."

Olivia de Havilland as Catherine Sloper
"The Heiress"
1949

The 1949 Academy Awards were held on March 23, 1950 at the RKO Pantages Theater in Hollywood.  Olivia picked up her second Oscar of her career that night for her performance in "The Heiress."  She was up against stiff competition including Susan Hayward, Deborah Kerr, and Loretta Young.

Oscar winners (L-R) Mercedes McCambridge (Supporting Actress), Broderick Crawford (Best Actor), Olivia deHavilland (Best Actress) and Dean Jagger (Best Supporting Actor) during 22nd annual Academy Awards at RKO Pantages theater.
  
Date taken: March 23, 1950  
Photographer: Ed Clark, Life Magazine

After receiving her second Best Actress Oscar in 1950, Olivia continued to be part of Oscar ceremonies as a presenter and special guest. 

25th Annual Academy Awards
March 19, 1953
RKO Pantages Theater, Hollywood &
NBC International Theater, New York
Aired on on NBC
First televised Oscar ceremonies
Olivia de Havilland - presenter of Best Director Oscar to John Ford for "The Quiet Man" 

32nd Annual Academy Awards
April 4, 1960
RKO Pantages Theater, Hollywood
Aired on NBC
Olivia de Havilland - presenter of the Best Supporting Actor Oscar to Hugh Griffith for "Ben-Hur" 

35th Annual Academy Awards
April 8, 1963
Santa Monica Civic Auditorium, Santa Monica
Aired on ABC
Olivia de Havilland - presenter of the Best Picture to
Sam Spiegel for "Lawerence of Arabia"

38th Annual Academy Awards
April 18, 1966
Santa Monica Civic Auditorium, Santa Monica
First time the Academy Awards were presented in color
Aired on ABC
Olivia de Havilland had a pre-recorded section recalling her previous awards and achievements.

39th Annual Academy Awards
April 10, 1967
Santa Monica Civic Auditorium, Santa Monica
Aired on ABC
Olivia de Havilland - presenter of Best Short Subject, Cartoons and Live Action Oscar for "Wild Wings," a 1966 Short Documentary Film.

40th Annual Academy Awards
April 10, 1968
Aired on ABC
Santa Monica Civic Auditorium, Santa Monica
Aired on ABC
Olivia de Havilland gave a pre-recorded presentation reviewing the previous decade of cinematic achievement

50th Annual Academy Awards
April 3, 1978
Dorothy Chandlier Pavilion, Los Angeles
Aired on ABC
Olivia de Havilland presented an honorary Oscar to Margaret Booth

60th Annual Academy Awards
April 11, 1988
Aired on ABC
Olivia de Havilland - Presenter for Best Art Direction and Set Design for the film "The Last Emperor"

75th Annual Academy Awards
March 23, 2003
Kodak Theater, Hollywood
Aired on ABC
Olivia de Havilland presented a tribute sequence to past Oscar winners

Olivia de Havilland was a presenter at the 50th Annual Academy Awards in 1978.  

Olivia was given the honor of presenting an honorary Oscar to Margaret Booth, a film editor with a career that spanned across 7 decades.  Her first project was "The Bridge of San Luis Rey" which was released in 1929.  Ms. Booth continued to work through the early 1980s.  She passed away in 2002 at the age of 104.  She was considered a pioneer in film editing and was one of the first female film editors.  

Read more about Ms. Margaret Booth here

Olivia de Havilland returned to the Oscars in 1988
and presented the Oscar for Best Art Direction and Set Design.

In 2003, Olivia de Havilland made a grand return to the Oscar stage to present 75 years of Oscar history.  It was an awesome moment as she walked on stage to the theme of Tara from Gone With the Wind.  She received a long applause and much deserved adulation from the audience.  She reminded us of the 75-year history of the Oscars and then presented to us a stage full of past Oscar winners stretching all the way back to the Classic Film Era.  It is a moment of television and Oscar history that I will not soon forget!