Which surfer character did Sean Penn play in Fast Times at Ridgemont High?
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His stoned surfer Jeff Spicoli became a pop-culture fixture.
For which 2003 Clint Eastwood film did Penn win his first Oscar?
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Mystic River won him Best Actor and the Golden Globe.
In the 2008 film Milk, Penn played which San Francisco politician?
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His portrayal of Harvey Milk won him a second Best Actor Oscar.
For which Paul Thomas Anderson film did Penn win Best Supporting Actor in 2026?
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He won Best Supporting Actor for One Battle After Another.
The 2010 earthquake in which country led Penn to found a relief organisation?
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Wrong!
He founded the J/P Haitian Relief Organization, later CORE, after the Haiti earthquake.
Which singer was Penn married to from 1985 to 1989?
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Penn’s marriage to Madonna drew intense press coverage.
What does the name of Penn’s charity CORE stand for?
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CORE stands for Community Organized Relief Effort.
Which film about Christopher McCandless did Penn direct?
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Penn adapted Jon Krakauer’s Into the Wild in 2007.
In which California city was Sean Penn born?
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He was born in Santa Monica and grew up in Malibu.
To the president of which country did Penn give one of his Oscars in 2022?
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Variety reported that Penn left an Oscar with President Zelensky in Kyiv.
Sean Penn Quiz: Easy Challenge
Getting Started
A few gaps to fill – the harder tiers are waiting.
Solid Knowledge
A good score. Try the Medium tier next.
Full Marks Territory
Excellent. The Legendary tier is where it gets difficult.
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