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You Takes Your Chances Trivia Quiz
Some stars don't stop when the script ends - they pick up the pen or step behind the camera. This quiz celebrates a few actors who rolled the dice, took creative risks, and ended up winning an Oscar for writing or directing. Do you remember these?
A classification quiz
by reedy.
Estimated time: 3 mins.
Last 3 plays: CardoQ (10/10), Guest 4 (8/10), Cinderella62 (3/10).
Place the celebrity actor into the correct category for their Oscar-winning achievement, for either Best Original Screenplay, Best Adapted Screenplay, or for Directing.
Original Screenplay
Directing
Adapted Screenplay
Kevin CostnerKenneth BranaghMel GibsonClint EastwoodRobert RedfordTaika WaititiBilly Bob ThorntonEmma ThompsonEmerald FennellSofia Coppola
* Drag / drop or click on the choices above to move them to the correct categories.
Sofia Coppola began her career in front of the camera, often in small or supporting roles, before gradually carving out a voice of her own behind the scenes. That voice came into full focus with "Lost in Translation" (2003), a quietly funny and deeply observant film she wrote and directed about loneliness and connection.
The screenplay's subtlety and emotional restraint earned Coppola the Academy Award for Best Original Screenplay (plus nominations for Best Director and Best Picture), marking her transition from actor to one of cinema's most distinctive writer-directors.
2. Emerald Fennell
Answer: Original Screenplay
Emerald Fennell transitioned from acting in period dramas and television to becoming one of the most daring new voices in film. Her sharp, unsettling script for "Promising Young Woman" (2020) stood out for its wit, anger, and modern edge. Winning the Oscar for Best Original Screenplay, Fennell proved she could shape cultural conversation not just by performing, but by writing stories that challenge expectations.
3. Kenneth Branagh
Answer: Original Screenplay
Kenneth Branagh spent years known primarily as a Shakespearean actor and director before turning inward for his most personal success. Drawing on his childhood in Northern Ireland, he wrote "Belfast" (2021), a gentle, heartfelt coming-of-age story told through a child's eyes. The Academy rewarded him with the Oscar for Best Original Screenplay, a milestone that confirmed Branagh's ability to transform personal memory into universally resonant cinema.
It should also be noted that Branagh was nominated as Best Director for the same film, although he lost out to Christopher Nolan and "Oppenheimer." Similarly, Branagh was previously nominated for Best Adapted Screenplay for his 1996 rendition of "Hamlet."
4. Robert Redford
Answer: Directing
Robert Redford was already a major movie star when he stepped behind the camera and quietly rewrote his career. His directorial debut, "Ordinary People" (1980), showed restraint and emotional intelligence rather than star power. The result was an Oscar win for Best Director, demonstrating that Redford's instincts as a storyteller were just as strong when guiding others as when performing himself.
Over a decade later, Redford earned another Oscar nomination for Best Original Screenplay for 1994's "Quiz Show," but had to defer the accolades to Quentin Tarantino and Roger Avary, who won for "Pulp Fiction."
5. Kevin Costner
Answer: Directing
Kevin Costner surprised Hollywood when he directed and starred in the sweeping western "Dances with Wolves" (1990). The project was ambitious, risky, and deeply personal, but his commitment paid off spectacularly. Costner won the Academy Award for Best Director, marking a rare transition from leading man to Oscar-winning filmmaker in a single bold move.
6. Clint Eastwood
Answer: Directing
Clint Eastwood spent decades defining himself as a rugged screen icon before quietly becoming one of Hollywood's most respected directors. His breakthrough behind the camera came with "Unforgiven" (1992), a reflective western that earned him an Academy Award for Best Director and signaled a new phase of his career. More than a decade later, Eastwood repeated the feat with "Million Dollar Baby" (2004), winning a second Oscar for directing and proving that his restrained, emotionally precise storytelling had only deepened with time.
Of course, Clint Eastwood's directing prowess was recognized on two other occasions at the Academy Awards, even though he did not win - he was also nominated for 2003's "Mystic River" and 2006's "Letters from Iwo Jima."
7. Mel Gibson
Answer: Directing
Though famous as an intense screen presence, Mel Gibson reshaped his legacy with "Braveheart" (1995). Directing a sweeping historical epic while also starring in it, he showed remarkable control of tone and scale. His Academy Award for Best Director cemented his reputation as a serious filmmaker rather than just an action star.
Twenty years later, Gibson was in the running for a second Oscar for Best Director with his work on "Hacksaw Ridge" (2016), but instead, the Oscar went to Damien Chazelle for "La La Land."
8. Emma Thompson
Answer: Adapted Screenplay
Emma Thompson is one of the few performers to find equal success as a writer. After establishing herself as a gifted actress, she adapted Jane Austen's 1811 novel into the 1995 film "Sense and Sensibility," balancing literary grace with emotional accessibility. Her Oscar win for Best Adapted Screenplay highlighted her rare ability to translate classic material into lively, modern cinema.
9. Billy Bob Thornton
Answer: Adapted Screenplay
Billy Bob Thornton's career took a dramatic turn when he wrote, directed, and starred in "Sling Blade" (1996), adapting his own earlier short film. The spare dialogue and haunting tone revealed a writer with a distinctive voice. Thornton won the Oscar for Best Adapted Screenplay, proving that his creative instincts extended far beyond acting.
10. Taika Waititi
Answer: Adapted Screenplay
Taika Waititi began as a performer known for offbeat humour before earning global recognition as a writer. With "Jojo Rabbit" (2019), he adapted Christine Leunens' dark 2008 novel "Caging Skies" into a satirical yet heartfelt film that balanced comedy with historical reflection.
His Oscar win for Best Adapted Screenplay confirmed his knack for reimagining difficult material with originality and empathy.
This quiz was reviewed by FunTrivia editor ponycargirl before going online.
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