Sean Penn, Milk | 24 Actors Who Won Oscars For Playing Real People | POPSUGAR Entertainment Photo 27
![Best actor winner Sean Penn (C) for "Milk" poses with his Oscar alongside Adrien Brody (L) and Michael Douglas backstage during the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike Best actor winner Sean Penn (C) for "Milk" poses with his Oscar alongside Adrien Brody (L) and Michael Douglas backstage during the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike](https://c8.alamy.com/comp/2D2NBDD/best-actor-winner-sean-penn-c-for-milk-poses-with-his-oscar-alongside-adrien-brody-l-and-michael-douglas-backstage-during-the-81st-academy-awards-in-hollywood-california-february-22-2009-reutersmike-blake-united-states-oscars-backstage-2D2NBDD.jpg)
Best actor winner Sean Penn (C) for "Milk" poses with his Oscar alongside Adrien Brody (L) and Michael Douglas backstage during the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike
![Sean Penn Vows to 'Smelt' His Oscar Statues if the 2022 Show Doesn't Include Ukraine President Sean Penn Vows to 'Smelt' His Oscar Statues if the 2022 Show Doesn't Include Ukraine President Sean Penn Vows to 'Smelt' His Oscar Statues if the 2022 Show Doesn't Include Ukraine President Sean Penn Vows to 'Smelt' His Oscar Statues if the 2022 Show Doesn't Include Ukraine President](https://cdn.justjared.com/wp-content/uploads/headlines/2022/03/sean-penn-will-melt-his-oscars.jpg)
Sean Penn Vows to 'Smelt' His Oscar Statues if the 2022 Show Doesn't Include Ukraine President Sean Penn Vows to 'Smelt' His Oscar Statues if the 2022 Show Doesn't Include Ukraine President
![Sean Penn, best actor winner for his role in "Milk," holds up his Oscar backstage at the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike Blake (UNITED STATES) (OSCARS-BACKSTAGE Stock Sean Penn, best actor winner for his role in "Milk," holds up his Oscar backstage at the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike Blake (UNITED STATES) (OSCARS-BACKSTAGE Stock](https://c8.alamy.com/comp/2E765PB/sean-penn-best-actor-winner-for-his-role-in-milk-holds-up-his-oscar-backstage-at-the-81st-academy-awards-in-hollywood-california-february-22-2009-reutersmike-blake-united-states-oscars-backstage-2E765PB.jpg)
Sean Penn, best actor winner for his role in "Milk," holds up his Oscar backstage at the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike Blake (UNITED STATES) (OSCARS-BACKSTAGE Stock
![81st Academy Awards® (2009) ~ Sean Penn won the Best Actor Oscar® for his performance in "Milk" (2008) | Best actor oscar, Hollywood celebrities, Actors 81st Academy Awards® (2009) ~ Sean Penn won the Best Actor Oscar® for his performance in "Milk" (2008) | Best actor oscar, Hollywood celebrities, Actors](https://i.pinimg.com/originals/cc/d7/02/ccd702d54fc57447704c9fc235f055c7.jpg)
81st Academy Awards® (2009) ~ Sean Penn won the Best Actor Oscar® for his performance in "Milk" (2008) | Best actor oscar, Hollywood celebrities, Actors
![Sean Penn with his award for Best Actor in a Leading Role for 'Milk', in the press room of the 81st Academy Awards ceremony, held at the Kodak Theater in Los Angeles, Sean Penn with his award for Best Actor in a Leading Role for 'Milk', in the press room of the 81st Academy Awards ceremony, held at the Kodak Theater in Los Angeles,](https://c8.alamy.com/comp/2E3F83N/sean-penn-with-his-award-for-best-actor-in-a-leading-role-for-milk-in-the-press-room-of-the-81st-academy-awards-ceremony-held-at-the-kodak-theater-in-los-angeles-ca-usa-on-february-22-2009-photo-by-lionel-hahnabacapresscom-2E3F83N.jpg)
Sean Penn with his award for Best Actor in a Leading Role for 'Milk', in the press room of the 81st Academy Awards ceremony, held at the Kodak Theater in Los Angeles,
![Sean Penn holds his Oscar for best actor for the film 'Milk' backstage at the 81st Academy Awards in Hollywood on February 22, 2009. (UPI Photo/Phil McCarten Stock Photo - Alamy Sean Penn holds his Oscar for best actor for the film 'Milk' backstage at the 81st Academy Awards in Hollywood on February 22, 2009. (UPI Photo/Phil McCarten Stock Photo - Alamy](https://c8.alamy.com/comp/TY115B/sean-penn-holds-his-oscar-for-best-actor-for-the-film-milk-backstage-at-the-81st-academy-awards-in-hollywood-on-february-22-2009-upi-photophil-mccarten-TY115B.jpg)
Sean Penn holds his Oscar for best actor for the film 'Milk' backstage at the 81st Academy Awards in Hollywood on February 22, 2009. (UPI Photo/Phil McCarten Stock Photo - Alamy
![Sean Penn holds up his best actor award for "Milk" backstage at the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike Blake (UNITED STATES) (OSCARS-BACKSTAGE Stock Photo - Alamy Sean Penn holds up his best actor award for "Milk" backstage at the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike Blake (UNITED STATES) (OSCARS-BACKSTAGE Stock Photo - Alamy](https://c8.alamy.com/comp/2D1BXBA/sean-penn-holds-up-his-best-actor-award-for-milk-backstage-at-the-81st-academy-awards-in-hollywood-california-february-22-2009-reutersmike-blake-united-states-oscars-backstage-2D1BXBA.jpg)
Sean Penn holds up his best actor award for "Milk" backstage at the 81st Academy Awards in Hollywood, California, February 22, 2009. REUTERS/Mike Blake (UNITED STATES) (OSCARS-BACKSTAGE Stock Photo - Alamy
![Focus Features on Twitter: "Happy Birthday to Sean Penn, whose Oscar-winning performance in #Milk won our hearts. https://t.co/6DMucQfjrM" / Twitter Focus Features on Twitter: "Happy Birthday to Sean Penn, whose Oscar-winning performance in #Milk won our hearts. https://t.co/6DMucQfjrM" / Twitter](https://pbs.twimg.com/media/CqFCdw9WYAAml_9.jpg:large)