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===George W. Bush administration=== [[File:March3.J27.UFPJ.WDC.27jan07.jpg|thumb|Penn at the [[January 27, 2007, anti-war protest|anti-Iraq War rally]] in Washington, D.C., in January 2007]] On October 18, 2002, Penn placed a $56,000 advertisement in ''[[The Washington Post]]'', publicly asking then President [[George W. Bush]] to end military hostilities in [[Iraq]] and elsewhere. The advertisement was written as an open letter and referred to the [[2003 invasion of Iraq|planned attack on Iraq]] and the [[War on terror]].<ref name="usatoday">{{cite news|first=Scott|last=Bowles|date=September 18, 2006|url=https://www.usatoday.com/life/movies/news/2006-09-18-sean-penn_x.htm|title=Sean Penn plays politics|newspaper=[[USA Today]]}}</ref> In the letter, Penn also criticized the Bush administration for its "deconstruction of [[civil liberties]]" and its "simplistic and inflammatory view of good and evil."<ref>{{cite web|url=http://www.snopes.com/inboxer/outrage/penn.asp |title=Sean Penn Letter to Washington Post |website=[[Snopes]] |date=November 24, 2002 |access-date=January 23, 2009}}</ref> Penn visited Iraq briefly in December 2002.<ref name="usatoday"/> The criticism drew praise from Penn's ex-wife [[Madonna]], who said, "Sean is one of the few. Good for him. Most celebrities are keeping their heads down. Nobody wants to be unpopular. But then Americans, by and large, are pretty ignorant of what's going on in the world."<ref>Rees, Paul: 'Listen very carefully, I will say this only once', ''[[Q (magazine)|Q]]'', May 2003, pp84-92</ref> The ''Post'' advertisement was cited as a primary reason for the development of his relationship with Venezuelan president [[Hugo Chávez]]. In one of his televised speeches, Chávez used and read aloud an open letter Penn wrote to Bush.<ref name="congeniality">{{cite news|url=https://www.telegraph.co.uk/culture/3668537/Sean-Penn-Mr-Congeniality.html |archive-url=https://ghostarchive.org/archive/20220110/https://www.telegraph.co.uk/culture/3668537/Sean-Penn-Mr-Congeniality.html |archive-date=January 10, 2022 |url-access=subscription |url-status=live|title=Sean Penn: Mr Congeniality|last=Somaiya|first=Ravi|date=October 14, 2007|work=[[The Daily Telegraph]]|access-date=February 12, 2012|location=London}}{{cbignore}}</ref> The letter condemned the [[Iraq War]], called for Bush to be [[Movement to impeach George W. Bush|impeached]], and also called then U.S. Vice President [[Dick Cheney]] and U.S. Secretary of State [[Condoleezza Rice]] "villainously and criminally obscene people."<ref>{{cite news|title=Sean Penn Praised by Venezuela's Chavez|url=https://www.washingtonpost.com/wp-dyn/content/article/2007/08/02/AR2007080200761.html|archive-url=https://web.archive.org/web/20150418055159/https://www.washingtonpost.com/wp-dyn/content/article/2007/08/02/AR2007080200761.html|archive-date=April 18, 2015|url-status=live|last=James|first=Ian|date=August 2, 2007|newspaper=[[The Washington Post]]|agency=[[Associated Press]]|access-date=August 22, 2021}}</ref> On April 19, 2007, Penn appeared on ''[[The Colbert Report]]'' and had a "Meta-Free-Phor-All" versus [[Stephen Colbert]] that was judged by [[Robert Pinsky]] following Penn's criticisms of Bush. In the appearance, Penn said, "We cower as you point your fingers telling us to support our troops. You and the smarmy pundits in your pocket– those who bathe in the moisture of your soiled and blood-soaked underwear–can take that noise and shove it."<ref>{{cite web |title = Sean Penn Unloads on Pres. Bush |url=https://www.foxnews.com/story/sean-penn-unloads-on-pres-bush |publisher=[[Fox News]]|date=March 27, 2007}}</ref> He won the contest with 10,000,000 points to Colbert's 1.<ref>{{cite web |url=http://crooksandliars.com/2007/04/21/stephen-colbert-vs-sean-penn/ |title=Stephen Colbert vs Sean Penn |website=[[Crooks and Liars]] |date=March 27, 2007}}</ref> On December 7, 2007, Penn said he supported Ohio Congressman [[Dennis J. Kucinich]] in the [[2008 U.S. presidential election]], and again criticized Bush's handling of the Iraq War. Penn questioned whether Bush's daughters, [[Jenna Bush|Jenna]] and [[Barbara Bush (born 1981)|Barbara]], supported the war in Iraq.<ref>{{cite web|first=Sean|last=Penn|url=https://www.huffingtonpost.com/sean-penn/an-open-letter-to-the-pre_2_b_44172.html|title=An Open Letter to the President...Four and a Half Years Later|website=[[HuffPost]]|date=March 24, 2007}}</ref>
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