The first Oscars for acting were presented for 1927/1928 to Emil Jannings (Best Actor) and Janet Gaynor (Best Actress).
Two: Best Actor and Best Supporting Actress.
Five: Best Picture, Director, Actor, Actress and Screenplay.
Katharine Hepburn won four Academy Awards during her distinguished career -- all for Best Actress.
Three: Best Actor (Henry Fonda), Actress (Katharine Hepburn) and Adapted Screenplay.
Jack Lemmon- Best Supporting Actor: Mister Roberts(1955), Best Actor: Save the Tiger (1973).Robert De Niro- Best Supporting Actor: The Godfather Part II (1974), Best Actor: Raging Bull (1980).Jack Nicholson- Best Actor: One Flew Over the Cuckoo's Nest (1975) and As Good As It Gets (1997), Best Supporting Actor: Terms of Endearment (1983).Gene Hackman- Best Actor: The French Connection(1971), Best Supporting Actor: Unforgiven (1992).Kevin Spacey- Best Supporting Actor: The Usual Suspects (1995), Best Actor: American Beauty (1999).Denzel Washington- Best Supporting Actor: Glory(1989), Best Actor: Training Day (2001).I'm adding the actresses who won both categories:Helen Hayes- Best Actress: The Sin of Madelon Claudet (1932), Best Supporting Actress: Airport(1970).Ingrid Bergman- Best Actress: Gaslight (1944) and Anastasia (1956), Best Supporting Actress: Murder on the Orient Express (1974).Maggie Smith- Best Actress: The Prime of Miss Jean Brodie (1969), Best Supporting Actress: California Suite(1978).Meryl Streep- Best Supporting Actress: Kramer vs. Kramer (1979), Best Actress: Sophie's Choice (1982) and The Iron Lady (2011).Jessica Lange- Best Supporting Actress: Tootsie(1982), Best Actress: Blue Sky (1994).Cate Blanchett - Best Supporting Actress: The Aviator (2002), Best Actress: Blue Jasmine (2013).
It is impossible for an actress to win best actor.
Two: Best Actor and Best Supporting Actress.
Technically, films do not win the Oscars for Best Actor or Best Actress. Actors and Actresses win these awards; however, they win these awards for specific performances in specific films, so here is the list of those films (and the actors who won the awards).Reversal of Fortune (1990) - Best Actor - Jeremy IronsMisery (1990) - Best Actress - Kathy BatesThe Silence of the Lambs (1991) - Best Actor - Anthony Hopkins - Best Actress - Jodie FosterScent of a Woman (1992) - Best Actor - Al PacinoHowards End (1992) - Best Actress - Emma ThompsonPhiladelphia (1993) - Best Actor - Tom HanksThe Piano (1993) - Best Actress - Holly HunterForrest Gump (1994) - Best Actor - Tom HanksBlue Sky (1994) - Best Actress - Jessica LangeLeaving Las Vegas (1995) - Best Actor - Nicolas CageDead Man Walking (1995) - Best Actress - Susan SarandonShine (1996) - Best Actor - Geoffrey RushFargo (1996) - Best Actress - Frances McDormanAs Good as It Gets (1997) - Best Actor - Jack Nicholson - Best Actress - Helen HuntLife Is Beautiful (1998) - Best Actor - Roberto BenigniShakespeare in Love (1998) - Best Actress - Gwyneth PaltrowAmerican Beauty (1999) - Best Actor - Kevin SpaceyBoys Don't Cry (1999) - Best Actress - Hilary Swank
In the acting catgories, there are 39 performers have won two or more Oscars to date. Here are the actors and actresses who have won exactly two Oscars as of 2014.Bette Davis, 2 Best Actress wins, 11 nominationsSpencer Tracy, 2 Best Actor wins, 9 nominationsMarlon Brando, 2 Best Actor wins, 8 nominationsJack Lemmon, 1 Best Actor, 1 Best Supporting win, 8 nominationsIngrid Bergman, 2 Best Actress, 1 Best Supporting win, 7 nominationsJane Fonda, 2 Best Actress wins, 7 nominationsDustin Hoffman, 2 Best Actor wins, 7 nominationsGary Cooper, 2 Best Actor wins, 6 nominationsMicahel Caine, 2 Best Supporting wins, 6 nominationsRobert DeNiro, 1 Best Supporting win, 1 Best Actor win, 6 nominationsMaggie Smith, 1 Best Actress win, 1 Best Supporting win, 6 nominationsJessica Lange, 1 Best Actress win, 1 Best Supporting win, 6 nominationsOlivia De Havilland, 2 Best Actress wins, 5 nominationsTom Hanks, 2 Best Actor wins, 5 nominationsFredric March, 2 Best Actor wins, 5 nominationsSean Penn, 2 Best Actor wins, 5 nominationsElizabeth Taylor, 2 Best Actress wins, 5 nominationsDenzel Washington, 1 Best Actor win, 1 Best Supporting win, 5 nominationsGene Hackman, 1 Best Actor win, 1 Best Supporting win, 5 nominationsJodie Foster, 2 Best Actress wins, 4 nominationsGlenda Jackson, 2 Best Actress wins, 4 nominationsAnthony Quinn, 2 Best Supporting wins, 4 nominationsShelley Winters, 2 Best Supporting wins, 4 nominationsMelvyn Douglas, 2 Best Supporting wins, 3 nominationsJason Robards, 2 Best Supporting wins, 3 nominationsPeter Ustinov, 2 Best Supporting wins, 3 nominationsDianne Wiest, 2 Best Supporting wins, 3 nominationsChristoph Waltz, 2 Best Supporting wins, 2 nominationsSally Field, 2 Best Actress wins, 2 nominationsVivien Leigh, 2 Best Actress wins, 2 nominationsLuise Rainer, 2 Best Actress wins, 2 nominationsHilary Swank, 2 Best Actress wins, 2 nominationsHelen Hayes, 1 Best Actress win, 1 Best Supporting win, 2 nominationsKevin Spacey, 1 Best Actor win, 1 Best Supporting win, 2 nominations
Sidney Poitier was first to win a Best Actor Oscar for the movie 'Lilies of the Field' (1963)Hattie McDaniel won Best Supporting Actress Oscar for her role as Mammy in 'Gone With the Wind' (1939) however the first Best Actress Award went to Halle Berry for Monster's Ball (2001)
Jamie Foxx is the only rap singer to win an Oscar. He won Best Actor for Ray (2004).
Two: Best Supporting Actor (Christian Bale) and Best Supporting Actress (Melissa Leo).
The Silence of the Lambs (1991).
Five: Best Picture, Director, Actor, Actress and Screenplay.
Katharine Hepburn won four Academy Awards during her distinguished career -- all for Best Actress.
Sidney Poitier was the first African-American to win a Best Actor award for his performance in "Lilies of the Field" (1963).
Sidney Poitier and Halle Berry. Poitier won the 1963 Academy Award as Best Actor for his performance in "Lilies of the Field." Berry won the 2001 Best Actress Oscar for her work in "Monster's Ball."