No male lead has ever won more than 2 best male lead actor nominations. The honor of having won 2 Oscars in the lead acting category is shared among 9 men, most recently as of the 2009 Academy Awards Sean Penn joined this group, winning for Milk and previously winning for Mystic River. The other male leads who share this honor are Spencer Tracy, Fredric March, Gary Cooper, Marlon Brando, Dustin Hoffman, Tom Hanks, Jack Nicholson, and Daniel Day-Lewis.
As I see it looking towards the 2009 season there really seems like only one of these men who stands a chance of winning a 3rd Lead Actor Oscar, and that is Daniel Day-Lewis who will be clearly the lead actor in the anticipated musical Nine. (Day-Lewis' previously wins were for My Left Foot, and recently for There Will Be Blood).
With the record breaking history that would be made with a Daniel Day-Lewis win, I can envision a nomination, but I feel like his previous wins would limit his chances of taking home an Oscar this upcoming year.
The other living "2 Lead Actor Winning Men" do not seem to have the type of roles and projects that could land them a nomination (Sean Penn has a supporting role in The Tree of Life that if the film is successful could lead to a nod, and a win would tie him with Jack Nicholson who has a supporting trophy alongside his lead wins).
While I ceratinly don't think the winner's guaranteed to come from this list of five, but I don't think it's completely out the picture to think that a 10th actor could join this list.
Here are 5 performances from previous winning actors that could potential lead to a second golden statue:
Phillip Seymore Hoffman, The Boat That Rocked
Previous win: Capote, 2005
Hoffman plays The Count (pictured above) in this period comedy about 1960s pirate radio with rogue DJs playing music off boats off the coast of England. The film co-stars Billy Nighy, and features Emma Thompson, January Jones, Kenneth Branagh, Nick Frost and Rhys Ifans.
Denzel Washington, The Taking of Pelham 1 2 3
Previous win: Training Day, 2001
Denzel Washingotn plays Zachary "Z" Garber, a hijack negotiator who has taken a New York subway train and it's passengers captive requesting a million dollar ransom. This summer blockbuster, is the third film adaptation of the novel with the same name wirtten Morton Freedgood under the name John Godey. The film is directed by action director Tony Scott and co-stars John Travolta along with James Gandolfini and Luis Guzmán.
Russell Crowe, State of Play
Previous win: Gladiator, 2000
Russell Crowe plays journalist Cal McCaffrey in this thriller based on the BBC miniseries. Crowe's becomes involving in investigating the death of a congressman's (Ben Affleck) mistress. Along with Crowe and Affleck, the film also features Helen Mirren, Viola Davis, Jeff Daniels, Jason Bateman, and Rachel McAdams. Michael Clayton director/writer shares writing credits in a film directed by Documentary Oscar winner Kevin MacDonald.
Kevin Spacey, Shrink
Previous win: American Beauty, 1999
Kevin Spacey plays a psychologist to top celebrities, but after a personal tradgedy, he becomes a drug addict and allows his own life to fall to pieces. In this independent film, Spacey's Hollywood clients include Robin Williams, Keke Palmer, Dallas Roberts, Pell James and Gore Vidal.
Nicolas Cage, Bad Lieutenant: Port of Call New Orleans
Previous win: Leaving Los Vegas, 1995
Nicolas Cage plays a corrupt, drug addict cop in New Orleans in this film directed by German documentarian Werner Herzog. The film will star Val Kilmer as Cage's partner as well as Eva Mendes, Xzibit, Jennifer Coolidge, and Fairuza Balk.