Keith followed his debut later that year with the holiday record Christmas to Christmas and returned with Blue Moon in 1996. Its first two singles went top ten and the third, "Me Too," became Keiths third number one, helping the album go platinum. He released Dream Walkin' in 1997 and "We Were in Love" and the title track were both Top Five hits, as was "I'm So Happy I Can't Stop Crying," a duet with Sting. He left Mercury in 1997 for a deal with DreamWorks.
Keith's Dreamworks debut, How Do You Like Me Now!, was released in 1999 and started to bring him wider recognition. The title cut went to number one on the country charts and brought him his first Top 40 pop hit. The album was won Keith his first awards, winning the 2001 Academy of Country Musics Male Vocalist of the Year and Album of the Year. Keith also began to cross over into acting, appearing on Touched by an Angel and in a Dukes of Hazzard TV movie as well as starring in commercials. His 2001 album Pull My Chain became his first Top Ten pop album, containing three number one singles.
Keith gained more attention amidst controversy over "Courtesy of the Red, White and Blue (The Angry American)", a song about the September 11 attacks. Some fans loved the songs patriotism, while others condemned it as ignorant. The media attention over his feud with Peter Jennings, who removed Keith from an ABC Fourth of July special because of the song, along with his spat with Dixie Chicks singer Natalie Maines both boosted Keiths popularity. The song went to number one on the country charts and crossed over into the pop Top 25. He soon released Unleashed, which debuted at number one on both the country and pop charts. "Who's Your Daddy" and the Willie Nelson duet "Beer for My Horses" were both country hits.
In 2003 Keith released Shock'n Y'All, and followed with Honkytonk University in May 2005, the same year that Mercury released Chronicles, a collection of three of his biggest albums. After departing from his longtime producer, Keith established his own company, Show Dog Nashville, and in 2006 released the label's first record, White Trash with Money. His 2006 tour will continue across the United States through October.
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