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Cheadle pertama kalinya mendapat perhatian luas atas perannya sebagai Mouse Alexander dalam film ''[[Devil in a Blue Dress (film)|Devil in a Blue Dress]]'', yang dengan itu ia memenangkan penghargaan Aktor Pendukung Terbaik dari [[Los Angeles Film Critics Association]] dan [[National Society of Film Critics]] serta dinominasikan pada penghargaan yang sama dari [[Screen Actors Guild]] dan[[NAACP Image Awards]]. Tak lama setelah itu, ia berperan dalam [[HBO]] TV 1996 ''[[Rebound: The Legend of Earl "The Goat" Manigault]]''. Dia juga membintangi film ''[[Volcano (1997 film)|Volcano]]''1997 yang disutradari oleh [[Mick Jackson (director)|Mick Jackson]].{{citation needed|date=June 2015}}
Karya-karya televisi Cheadle termasuk penampilan nominasi -[[Emmy]] dalam film-film ''[[The Rat Pack (film)|The Rat Pack]]'', ''[[A Lesson Before Dying]]'', ''[[Things Behind the Sun]]'' dan sebagai bintang tamu dalam ''[[ER (TV series)|ER]]''. The last of these spanned four episodes during the show's ninth season, in which he portrayed Paul Nathan, aseorang medicalmahasiswa studentkedokteran strugglingyang toberjuang copeuntuk withmengatasi [[Parkinson's disease|penyakit Parkinson]]. HeDia hastelah madebanyak appearancestampil indalam filmsfilm includingtermasuk ''[[Rosewood (film)|Rosewood]]'', ''[[The Family Man]]'', ''[[Boogie Nights]]'', asebuah penampilan cameo appearance in thedalam film ''[[Abby Singer (film)|Abby Singer]]'', ''[[Out of Sight (1998 film)|Out of Sight]]'', ''[[Traffic (2000 film)|Traffic]]'', and ''[[Ocean's Eleven]]''. TheseKetiga last threefilm wereini directeddisutradarai byoleh [[Steven Soderbergh]]. InPada 2005, Cheadle was nominated for thedinominasikan [[Academy Award for Best Actor|Aktor Terbaik Academy Award]] foratas hisperannya portrayalsebagai of [[Paul Rusesabagina]] in thedalam film ''[[Hotel Rwanda]]''. He also starred in and co-produced ''[[Crash (2004 film)|Crash]]'', which won the 2005 [[Academy Award for Best Picture]]. ForAtas hispenampilannya performance indalam ''Crash'', Cheadle wasdinominasikan nominatedsebagai forAktor thePendukung Terbaik untuk penghargaan [[BAFTA]] anddan [[Screen Actors Guild]] Awards for Best Supporting Actor. HeDia playedmemerankan thetokoh mainutama characterdalam in the moviefilm ''[[Traitor (film)|Traitor]]''. InPada MarchMaret 2007, Cheadle starredmembintangi withfilm comediankomedi bersama [[Adam Sandler]] in<nowiki/>dalam Mike Binder's ''[[Reign Over Me]]'', asebuah comedydrama-dramakomedi abouttentang aseorang manpria whoyang hasmelarikan slippeddari awaykehidupan fromnyata realitysetelah afteristrinya hisdan wifetiga andputrinya threemeninggal daughters dieddunia. AfterSetelah playingtayang forselama 38 dayshari, the film becametersebut masuk dalam ajajaran [[box office bomb|box office flop]] earningdengan apendapatan domestic gross of onlykotor 22.,2 millionjuta. Cheadle laterkemudian starred in the 2009 DreamWorks Picturesmembintangi film ''[[Hotel for Dogs]] pada 2009 garapan DreamWorks Picture''.<ref>{{cite web|url=http://www.azcentral.com/ent/movies/articles/2008/10/14/20081014cheadle.html|title=Don Cheadle joins 'Iron Man 2'|publisher=Azcentral.com|date=October 14, 2008|accessdate=July 28, 2010}}</ref><ref>{{cite web|url=http://www.movieweb.com/news/NEDZSGFF0tRZIE|title=Don Cheadle Joins Hotel for Dogs |publisher=Movieweb.com|accessdate=July 28, 2010}}</ref>
InPada 2007, Cheadle publishedmenerbitkan asebuah bookbuku, ''[[Not on Our Watch]]: The Mission to End Genocide in Darfur and Beyond'', cobermitra-authoredtulis withdengan [[John Prendergast (activist)|John Prendergast]]. Cheadle wasdiharapkan to make his directorialmembuat debut withsutradaranya thedengan adaptation ofpenyesuaian [[Elmore Leonard]]'s ''[[Tishomingo Blues (novel)|Tishomingo Blues]]''. InDalam asebuah Julywawancara 2007Juli interview2007 heia statedmenyatakan, "'Tishomingo' issudah deadtiada..."<ref name=autogenerated1>{{cite web|url=http://www.comingsoon.net/news/movienews.php?id=21703 |title=Don Cheadle Talks to Us |publisher=Comingsoon.net |date=July 6, 2007 |accessdate=July 28, 2010}}</ref>
Cheadle appeared in [[National Football League|NFL]] commercials promoting the [[Super Bowl]] from 2002 to 2005. He so regularly appeared for the NFL in its Super Bowl advertising that in 2006, in a drive to get fans to submit their own advertising ideas, the NFL sought his permission to reference his previous commercials to portray themselves as having no new ideas: "he quickly signed off on the idea and found it funny." Abe Sutton (along with Etan Bednarsh), one of the finalists in this NFL contest, played on this commercial by proposing an ad where an entire team of football players are Don Cheadle.<ref>{{cite web|last=Thomaselli|first=Rich|url=http://adage.com/article?article_id=112930|title=Advertising Age|publisher=Adage.com |date=November 2, 2006|accessdate=July 28, 2010}}</ref>
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