Many lists of Academy Award trivia focus on milestones like “The first…” or “The only…”. This one includes some of those, but I’ve added a few that you might not know. I selected these because they each have an interesting tale about the win or the winner. My goal is for each one to make you think, “I didn’t know that.” If you have your own interesting Oscar stories, share them in the comments below.
10. George Bernard Shaw Two Prestigious Awards

Received: Best Writing (Screenplay) for Pygmalion in 1938
It’s a remarkable feat to receive the highest accolades in two completely different fields. As of now, only one person has won both an Academy Award and a Nobel Prize—George Bernard Shaw, who was honored with the Nobel in Literature in 1925. Before you rush to correct me, I recommend reading through the rest of the list first.
9. Dudley Nichols The First Refusal

Awarded: Best Writing (Screenplay) in 1935 for The Informer
While Marlon Brando famously sent Sacheen Littlefeather to decline his Oscar for The Godfather as a protest against the treatment of Native Americans, and George C. Scott rejected his for Patton, criticizing the concept of competing with fellow actors and calling it a ‘meat parade,’ Dudley Nichols was the first to ever refuse the highest cinematic honor. He turned down his Academy Award due to the writer’s guild strike. Eventually, he reversed his decision and accepted the Oscar before 1949.
8. Winners Who Didn’t Win

Pierre Boulle (The First Fake Winner): Best Writing (Adapted) in 1957 for The Bridge on the River Kwai. Nathan E. Douglas (The First Pseudonym Winner): Best Writing (Original) in 1958 for The Defiant One, Best Writing (Adapted) in 1960 for Inherit the Wind
It’s a common assumption that the winner of an Academy Award is a real, living person. However, during Hollywood’s Blacklist Era, many had to conceal their work behind false credits in order to continue their craft.
Peter Boulle is a real French writer, though he is said to not write in English. Nevertheless, he penned The Bridge Over the River Kwai. His name was used as a cover by Michael Wilson and Carl Foreman when adapting his book. When the truth came to light after the Blacklist Era, Boulle declined the Oscar, but Wilson and Foreman received theirs in 1984.
Nathan E. Douglas was the pseudonym used by Nedrick Young during the Blacklist Era. Under this name, he won two Academy Awards. In 1993, his true identity was restored on the nominee and award lists, and his son was given the Oscars in his place.
It’s unfortunate that Donald Kaufman didn’t win for his screenplay of Adaptation. He remains the first nominee to never have existed in any form.
7. Sidney Howard The First Posthumous Winner

Won the Oscar for Best Writing (Screenplay) in 1939 for *Gone With the Wind*.
This Oscar marked Howard’s third, although tragically, he was never able to receive it. He passed away in a strange gardening accident when a tractor he was using ran over him. Incidentally, Howard also won a Pulitzer Prize, and further research (or a commenter) may reveal whether he was the first to win both. It seems likely, especially given that he claimed his first Oscar just five years into the awards’ history.
6. Luise Rainer, the First to Win Twice

Won: Best Actress in 1936 for *The Great Ziegfeld*, and again in 1937 for *The Good Earth*.
Luise Rainer became the first person in Oscar history to win back-to-back Best Actress awards, achieving the feat with just her second and third English-speaking roles. She triumphed over formidable competitors like Janet Gaynor, who starred in *A Star is Born*, and Greta Garbo, who shone in *Camille*, earning the accolade in 1937. In fact, her victory was such a surprise that she skipped the award ceremony that year, having been seen as a long shot.
After her career took a downturn, largely due to her own misguided choices, the idea of the 'Oscar Jinx' began to spread (ask Cuba Gooding about it). Her reputation had declined so significantly by the end of her career that, as legend has it, when Raymond Chandler was worrying about the upcoming ceremony where *Double Indemnity* was nominated, his wife remarked that the Oscar didn’t really matter since 'After all, Luise Rainer won it twice.'
5. Only Winners

*Sunrise*: Best Picture (for artistic production) 1927/8 Roy Pomeroy: Best Engineering Effects 1927/8 for *Wings* Joseph Farnham: Best Title Writing 1927/8 (no specific film)
What would it be like to be the sole winner of a particular award? These three individuals are the only ones to ever win in their respective categories. Initially, there were two Best Picture awards. The one that *Wings* received that year was for Best Picture (outstanding production), and it is this version that evolved into the current Best Picture award. The Engineering Effects Oscar went to *Wings* for its groundbreaking aerial cinematography, defeating Nugent Slaughter's work for *The Jazz Singer* (though Warner Brothers still earned a special award for it). *The Jazz Singer* also made the Best Title Writing category obsolete by the following year. Gerald Duffy, nominated for Best Title Writing for *The Private Life of Helen of Troy*, could have been number 11 on this list, but he lost and became the first posthumous nominee.
Other awards have appeared to be one-time-only honors, like those for art direction and sound recording at the fourth Oscar ceremony. These awards reflect the evolution and changes in Oscar categories over time, part of the legacy of continually adapting awards. These three categories are the only ones to officially have just a single winner.
4. Martin Scorsese

Three 6 Mafia: Best Original Song 2005 for 'It’s Hard Out Here for a Pimp' Martin Scorsese: Best Director 2006 for *The Departed*.
Martin Scorsese was long regarded as a masterful filmmaker, consistently earning multiple nominations (seven in total for writing and directing between 1980 and 2004) but never taking home an Oscar. When Three 6 Mafia won for Best Original Song, host Jon Stewart quipped, 'Three 6 Mafia, one Oscar. Martin Scorsese, no Oscars,' to the amusement of the audience. But Scorsese would finally take home the award the following year.
3. Orson Welles and Charlie Chaplin

Orson Welles: Best Original Screenplay 1941 for *Citizen Kane* Charlie Chaplin: Best Original Dramatic Score 1972 for *Limelight*.
It’s often pointed out how certain cinematic geniuses never received an Oscar, or at best, were only awarded honorary ones. Two of the most frequently cited examples are Orson Welles and Charlie Chaplin. Ironically, both of them did win Oscars.
Charlie Chaplin received an honorary Oscar at the very first Academy Awards ceremony for *The Circus*. Some interpret this award as a recognition of his work's excellence, suggesting that if he had competed, it would have been a one-man show. Others correctly argue that it wasn’t a competitive award. I tend to agree with the former interpretation, particularly since the Academy sent Chaplin a letter stating: 'The Academy Board of Judges on merit awards for individual achievements in motion picture arts during the year ending August 1, 1928, unanimously decided that your name should be removed from the competitive classes, and that a special first award be conferred upon you for writing, acting, directing, and producing *The Circus*. The collective accomplishments thus displayed place you in a class by yourself.'
This issue was somewhat resolved in 1972, when Chaplin won the Oscar for Best Original Score for *Limelight*. The rules at the time (which have since changed) made it eligible 20 years after its release. Eligibility was based on the first time a film was shown in Los Angeles, and Chaplin had kept *Limelight* from being shown in the L.A. market until 1972.
As for Orson Welles, the situation is a bit more straightforward. While it's true that he never won an Oscar for directing or acting, he did win an Academy Award for his screenplay for *Citizen Kane*, which he shared with Herman J. Mankiewicz.
2. Davis Guggenheim Though he doesn’t have a Nobel Prize, he does have an Oscar.

Won: Best Documentary (Feature) 2006 for *An Inconvenient Truth*.
Yes, he authored the book. Yes, he narrated the film. Yes, he accepted the statuette from the presenter. Yes, he delivered the acceptance speech that everyone remembers. No, he did not win the Oscar.
The winner of the Academy Award for *An Inconvenient Truth* was producer/director Davis Guggenheim, not Albert Gore, Jr.
1. Metro-Goldwyn-Mayer

Won: Best Short Subject (Cartoon) 1940 for *The Milky Way*.
The award had been presented thirteen times, but it was only on this occasion that Disney didn't claim the prize. In fact, Disney wasn't even nominated that year—did they even release a film? Following that, Disney secured the next two awards, after which M.G.M. dominated for the next four years. However, on the 20th anniversary of the award, Warner Brothers broke the streak with 'Tweety Pie,' marking the debut of Sylvester and Tweety.
