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===1999β2001: ''On How Life Is''=== Gray worked on her debut album in 1999 with producer [[Darryl Swann]].<ref name="latimes2007">{{cite news| url= https://www.latimes.com/archives/la-xpm-2007-mar-25-ca-rack25-story.html | work=Los Angeles Times | title=Odd charm works only so long for Macy Gray | date=March 25, 2007 | access-date=May 12, 2010 | first1=Richard | last1=Cromelin | first2=Natalie | last2=Nichols | first3=Soren | last3=Baker}}</ref> Released in the summer of 1999, ''[[On How Life Is]]'' became a worldwide smash.<ref>{{cite web |url=http://www.sonybmg.com.au/artist/artistSiteLink.do?artistId%3D12467 |title=Archived copy |access-date=October 27, 2008 |url-status=dead |archive-url=https://web.archive.org/web/20081208132300/http://www.sonybmg.com.au/artist/artistSiteLink.do?artistId=12467 |archive-date=December 8, 2008}}</ref> The first single, "[[Do Something (Macy Gray song)|Do Something]]", stalled on the charts, but the second single, "[[I Try]]", made the album a success.<ref>{{cite news| url=https://www.independent.co.uk/arts-entertainment/music/features/macy-gray-the-new-voice-of-soul-723699.html | archive-url=https://web.archive.org/web/20081208030452/http://www.independent.co.uk/arts-entertainment/music/features/macy-gray-the-new-voice-of-soul-723699.html | url-status=dead | archive-date=December 8, 2008 | work=[[The Independent]] | location=London | title=Macy Gray: The new voice of soul | first=David | last=Usborne | date=March 4, 2000 | access-date=April 5, 2010}}</ref> "I Try" (which was originally featured in ''[[Love Jones (film)|Love Jones]]'' and the [[Jennifer Aniston]]-starring romantic-comedy ''[[Picture Perfect (1997 film)|Picture Perfect]]'' in 1997)<ref>{{cite web| url= https://www.popmatters.com/music/reviews/g/graymacy-trouble.shtml |first=Cynthia|last=Fuchs| title=Macy Gray: The Trouble With Being Myself β PopMatters Music Review |work=PopMatters |date=August 1, 2003|archive-url=https://web.archive.org/web/20030802161536/http://popmatters.com/music/reviews/g/graymacy-trouble.shtml|archive-date=August 2, 2003|url-status=dead|access-date=January 2, 2011}}</ref> was one of the biggest singles of 1999,<ref>{{cite web | url=http://www.alaskajim.com/charts/yearlysingles/1999.asp | title=Top Songs of 1999 β US Singles Charts | website=Alaskajim.com | access-date=January 2, 2011 | archive-date=November 1, 2008 | archive-url=https://web.archive.org/web/20081101004113/http://www.alaskajim.com/charts/yearlysingles/1999.asp | url-status=dead }}</ref><ref>{{cite web|url=http://allcharts.org/music/years/usa-singles-1999.htm |title=USA Top Singles For 1999 |publisher=Allcharts.org |access-date=January 2, 2011}}</ref> and subsequent singles ("[[Still (Macy Gray song)|Still]]" and "[[Why Didn't You Call Me]]") ensured the album became triple platinum in the U.S.<ref>{{cite news| url= https://www.independent.co.uk/arts-entertainment/music/reviews/first-night-macy-gray-koko-london-443292.html | archive-url= https://web.archive.org/web/20081208030457/http://www.independent.co.uk/arts-entertainment/music/reviews/first-night-macy-gray-koko-london-443292.html | url-status= dead | archive-date= December 8, 2008 | work=[[The Independent]] | location=London | title=First Night: Macy Gray, Koko, London | first=Ben | last=Walsh | date=April 4, 2007 | access-date=April 5, 2010}}</ref> and quadruple platinum in the UK.<ref name=cinnerview>{{cite web| url= http://www.chicagoinnerview.com/archives/jan04_macy_gray.htm| title= Macy Gray| first= Jim | last= Famera| archive-url= https://web.archive.org/web/20090212202605/http://www.chicagoinnerview.com/archives/jan04_macy_gray.htm |date= January 2003| archive-date=February 12, 2009}}</ref> In [[43rd Grammy Awards|2001]], Gray won the [[Grammy Award for Best Female Pop Vocal Performance]] for "I Try", which was also nominated for the [[Grammy Award for Song of the Year|Song of the Year]] and [[Grammy Award for Record of the Year|Record of the Year]] Grammys.<ref>{{cite news|url=http://archives.cnn.com/2001/SHOWBIZ/Music/02/21/grammy.night.01/index.html |work=[[CNN]] |url-status=dead |title=Madonna, Macy kick off Grammys |date=February 21, 2001|first=Jamie|last=Allen| archive-url=https://web.archive.org/web/20080504091622/http://archives.cnn.com/2001/SHOWBIZ/Music/02/21/grammy.night.01/index.html |archive-date=May 4, 2008 }}</ref> She then collaborated with [[Fatboy Slim]], the Black Eyed Peas, and [[Slick Rick]] (on the song "The World Is Yours", from the ''[[Rush Hour 2]]'' soundtrack), as well as acting for the first time, in the thriller ''[[Training Day]]''.<ref>{{cite web|last=Moss |first=Corey |url=http://www.mtv.com/news/articles/1445242/20010718/gray_macy.jhtml |archive-url=https://web.archive.org/web/20010721080917/http://www.mtv.com/news/articles/1445242/20010718/gray_macy.jhtml |url-status=dead |archive-date=July 21, 2001 |title=Macy Gray, Ludacris, LL Cool J On 'Rush Hour 2' Soundtrack β Music, Celebrity, Artist News |publisher=[[MTV]] |date=July 18, 2001 |access-date=January 2, 2011}}</ref> In August 2001, Gray was booed at the [[Pro Football Hall of Fame Game|Pro Football Hall of Fame exhibition game]] after forgetting the lyrics to the [[American national anthem]].<ref>{{cite news |url=https://www.washingtonpost.com/wp-srv/aponline/20010807/aponline133518_000.htm |archive-url=https://web.archive.org/web/20121111235956/http://www.washingtonpost.com/wp-srv/aponline/20010807/aponline133518_000.htm |url-status=dead |archive-date=November 11, 2012 |title=Macy Gray Is Booed During Anthem |access-date=May 26, 2007|date=August 7, 2001 |newspaper=[[The Washington Post]]}}</ref>
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