Can Sean Penn win two Oscars within five years?
The best actor category -- in which comeback kid Mickey Rourke ("The Wrestler"), veteran thespian Frank Langella ("Frost/Nixon"), and the category's 2003 winner Sean Penn ("Milk") are duking it out for top honors -- has proven to be of the hottest races of this year's awards season.
To win, each man would have to overcome some major obstacles: during his dark days, Rourke ticked off a lot of people who have long memories, and even these days his unusual appearance and frank manner freak out a lot of others; Langella has very openly expressed that theater is his medium of choice and that he tends to appear in films only to help pay the bills, which may offend some; and Penn has a whole retinue of issues, not least of which is that he essentially refuses to campaign for himself.
Those are all legitimate, real concerns. What is not is something I've heard discussed a lot lately by people who are supporting and/or predicting someone other than Penn to win: namely, that there is no way that the academy would give the same person two Oscars within 5 years.
That's just plain wrong, and here are 16 reasons why:
Lead Categories
- Bette Davis, best actress for "Dangerous" (1935) and "Jezebel" (1938)
- Luise Rainer, best actress for "The Great Ziegfeld" (1936) and "The Good Earth" (1937)
- Spencer Tracy, best actor for "Captains Courageous" (1937) and "Boy's Town" (1938)
- Olivia de Havilland, best actress for "To Each His Own" (1946) and "The Heiress" (1949)
- Katharine Hepburn, best actress for "Guess Who's Coming to Dinner?" (1967) and "The Lion in Winter" (1968)
- Glenda Jackson, best actress for "Women in Love" (1970) and "A Touch of Class" (1973)
- Sally Field, best actress for "Norma Rae" (1979) and "Places in the Heart" (1984)
- Jodie Foster, best actress for "The Accused" (1988) and "Silence of the Lambs" (1991)
- Tom Hanks, best actor for "Philadelphia" (1993) and "Forrest Gump" (1994)
- Hilary Swank, best actress for "Boys Don't Cry" (1999) and "Million Dollar Baby" (2004)
Supporting Categories
- Walter Brennan, best supporting actor for "Come and Get It" (1936), "Kentucky" (1938), and "The Westerner" (1940)
- Anthony Quinn, best supporting actor for "Viva Zapata" (1952) and "Lust for Life" (1956)
- Peter Ustinov, best supporting actor for "Spartacus" (1960) and "Topkapi" (1964)
- Jason Robards Jr., best supporting actor for "All the President's Men" (1976) and "Julia" (1977)
Combination
- Meryl Streep, best supporting actress for "Kramer vs. Kramer" (1979) and best actress for "Sophie's Choice" (1982)
- Kevin Spacey, best supporting actor for "The Usual Suspects" (1995) and best actor for "American Beauty" (1999)
Photo: Sean Penn in "Milk." Credit: Focus Features


Scott Feinberg is a film industry awards analyst. He boasts one of the best track records at projecting the Academy Awards, including a 21 for 24 effort in 2006, first among all pundits according to OscarCentral and Variety. Feinberg, who studied film at Yale University and Brandeis University, is the founder of
all in all, I think the oscar should be rourke's - it's a stunning performance from a man that everyone thought was finished. the cheers he got at the globes suggest he's been forgiven by his peers too.
Posted by: soosie | January 27, 2009 at 01:37 AM
Sean deserves the Oscar for Milk. I hope he wins. If you deserve it, it shouldn't matter how many you've won before or when.
Posted by: Kelly | January 27, 2009 at 05:47 AM
Sean Penn has grown so much over the last five years which has allowed him be a master in his art.
Is it really that interesting whether he wins the oscar two times in five years ?
This amazingly honest and gut wrenching role has opened peoples hearts and minds to discuss things like civil & human rights and how we must do better NOW!
We are all human beings and do deserve to have our voice heard.
I loved all of this years Oscar picks, but this film really hit me as a human rights activist.
Posted by: Laurie Coleman | January 27, 2009 at 11:23 AM
What has the clothes that Mickey Rourke wears have to do with a performance that was outstanding. I do not find him scary based on his wordrobe but it just shows his individuality. I also find his frank manner as you put it very refreshing and again has nothing to do with his steller performance. These are not real concerns but excuses.
Posted by: marcia silverstein | January 28, 2009 at 11:26 AM
Penn was great. But Rourke edges out Penn for the best actor Oscar this year. An iconic performance, like Brando in Streetcar and DeNiro n Raging Bull. Rourke's peers always respected his unique acting, excepting Basinger and Kidman.
Posted by: denir | January 28, 2009 at 05:47 PM
Dude. Denir, comparing Mikey Rourke's performance to Marlon Brando in Streetcar? I hope I didn't just see that. I have no intentions to see "The Wrestler" because it's about wrestling. I mean, seriously. I know everyone is a sucker for a comeback and all, but just because it's a "comeback" doesn't mean you're entitled now for an Oscar.
Sean Penn's performance is untouchable. It doesn't matter if it's in a time span of 5 years or 3 or even 1 for that matter, he deserves it more than anyone else. "Milk" was absolutely phenomenal.
Posted by: Kat | January 29, 2009 at 12:09 AM