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Womack's first MCA studio album and third overall was 2000's ''[[I Hope You Dance]]'' which met with major success. It produced a total of four singles, which made the Top 40 on the ''Billboard'' country singles charts. The album was led off by the single "[[I Hope You Dance (song)|I Hope You Dance]]", a collaboration with the country music band [[Sons of the Desert (band)|Sons of the Desert]]. It became the most successful single off the album with a number 1 peak on the ''Billboard'' country singles chart and a number 14 peak on the [[Billboard Hot 100|Hot 100]] charts, representing Womack's and Sons of the Desert's highest peaks on those charts. It was followed by a cover of [[Rodney Crowell]]'s "Ashes by Now", "Why They Call it Falling", and a cover of [[Buddy Miller]]'s "[[Does My Ring Burn Your Finger]]". Also included on this album was a cover of [[Don Williams]]' "[[Lord, I Hope This Day Is Good]]". "I Hope You Dance" won the Country Music Association's "Song of the Year" and "Single of the Year" awards.<ref name="CMA"/> ''I Hope You Dance'' also earned Womack's first [[Grammy Award]] nomination at the [[43rd Annual Grammy Awards]] in February 2001, in the categories of Best Country Album and Best Female Country Vocal Performance.<ref name="grammy">{{cite web | url=https://www.grammy.com/artists/lee-ann-womack/17593 | title=Search results for Lee Ann Womack | publisher=Grammy.com | accessdate=July 11, 2024 | archive-date=March 3, 2024 | archive-url=https://web.archive.org/web/20240303080839/https://www.grammy.com/artists/lee-ann-womack/17593 | url-status=live }}</ref> In 2002, ''I Hope You Dance'' was certified triple-platinum by the RIAA for shipments of 3 million copies.<ref name="riaa"/> In Canada, the album was certified double-platinum by the Canadian Recording Industry Association (now [[Music Canada]]), a certification which at the time honored shipments of 200,000 copies in that country.<ref name="cria">{{cite web | url=https://musiccanada.com/gold-platinum/?_gp_search=lee%20ann%20womack | title=Search results for The Mavericks | publisher=[[Music Canada]] | accessdate=July 4, 2024}}</ref>{{efn|In May 2008, Music Canada reduced the qualification for double-platinum sales from 200,000 to 160,000.<ref>{{cite web | url=https://musiccanada.com/certification/ | title=Certification | publisher=Music Canada | accessdate=July 4, 2024 | archive-date=July 14, 2014 | archive-url=https://web.archive.org/web/20140714220020/http://musiccanada.com/certification/ | url-status=live }}</ref>}}
In 2002, MCA released Womack's fourth studio album, ''[[Something Worth Leaving Behind]]''. It was led off by the single "[[Something Worth Leaving Behind (song)|Something Worth Leaving Behind]]", which charted at 20 on Hot Country Songs. Its follow up was "[[Forever Everyday]]", which peaked at number 37 on Hot Country Songs that year. On this album, Womack co-produced with Wright, her husband [[Frank Liddell]], and [[Mike McCarthy (producer)|Mike McCarthy]]. Writing for ''[[USA Today]]'', Brian Mansfiled described it as the tenth worst album of 2002, saying "Womack's ill-advised [[Crossover music|crossover]] ploy and a makeover that made her look like [[Britney Spears]]' [[Lynne Spears|mother]] made one of Nashville's most respected singers the butt of jokes."<ref>Mansfield, Brian. ''USA Today'' Alan drives country; 'Country' goes in ditch (December 31, 2002)</ref> David Cantwell of [[No Depression (magazine)|''No Depression'']] said "The results, no matter which side of the pop-twang divide you're on, will likely be very disappointing."<ref>{{Cite web |last=Cantwell |first=David |title=Lee Ann Womack – Something Worth Leaving Behind |url=http://nodepression.com/album-review/lee-ann-womack-something-worth-leaving-behind |website=No Depression |publication-date=October 31, 2002|accessdate=July 10, 2024}}</ref> [[Stephen Thomas Erlewine]] of [[AllMusic]] thought the album "was a sure fit for Womack to move into the country mainstream for good."<ref name="allmusic"/> Thom Jurek, also of AllMusic, said in a retrospective review that the album "cemented Womack's place in the country music pantheon by pushing her own boundaries as an artist further than ever before."<ref name="jurek swlb">{{cite web |last=Jurek |first=Thom |title=''Something Worth Leaving Behind'' review |url=https://www.allmusic.com/album/something-worth-leaving-behind-mw0000223570 |access-date=July 10, 2024 |work=All Music |publisher=All Media Network |archive-date=June 5, 2024 |archive-url=https://web.archive.org/web/20240605004641/https://www.allmusic.com/album/something-worth-leaving-behind-mw0000223570 |url-status=live }}</ref> Womack told Mario Tarradell of ''The Dallas Morning News'' in 2005, "I tried...to please everybody with that record...myself, radio, the listeners, everybody who loved 'Never Again, Again' and everybody who loved 'I Hope You Dance.' And it just didn't work. It backfired."<ref>Tarradell, Mario. ''The Dallas Morning News'' Country beckons her back (February 27, 2005)</ref>
In 2004, Womack performed "I Hope You Dance" at the [[Republican National Convention]], in which [[George W. Bush]] was nominated for his second term as President of the United States. The other performers that night included [[Sara Evans]] and [[Larry Gatlin]].<ref>{{cite news|url=http://www.cnn.com/2004/ALLPOLITICS/08/29/gop.lineup/index.html|title=GOP convention aims at moderates|last=Patterson|first=Thom|publisher=CNN|access-date=November 29, 2008|date=August 30, 2004|archive-date=December 19, 2008|archive-url=https://web.archive.org/web/20081219113113/http://www.cnn.com/2004/ALLPOLITICS/08/29/gop.lineup/index.html|url-status=live}}</ref> She also collaborated with Red Dirt Music band [[Cross Canadian Ragweed]] on their hit "Sick and Tired" in 2004. Also that year, she released her first ''[[Greatest Hits (Lee Ann Womack album)|Greatest Hits]]'' compilation, which included two new songs; "The Wrong Girl" and "Time for Me to Go", the former released as a single. The ''Greatest Hits'' album was also certified gold by the RIAA in December 2008.<ref name="riaa"/>
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