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Through extensive promoting, including appearances on MTV (including a performance alongside Aerosmith and Run-DMC) and performing at Woodstock 1999, Devil Without a Cause sold 14 million copies, the album's success spurred by Kid Rock's breakthrough hit single "Bawitdaba".In May 2000, Kid Rock released the compilation album " The History Of Rock", behind the single "American Bad Ass".
Through extensive promoting, including distributing tapes on consignment to local stores and giving away free samplers of his music, Kid Rock developed a following among an audience which DJ Uncle Kracker described as "white kids who dropped acid and liked listening to gangsta rap"; this following included local rapper Joe C, who had been attending Kid Rock concerts as a fan, but upon meeting Kid Rock, was invited to perform on stage as Kid Rock's hype man.In November of that year, he released his eleventh studio album, Sweet Southern Sugar.The same year also saw Kid Rock publicly advocate measures against ticket scalpers at his shows by making tickets more affordable for fans.He's a rock star and everything in between." In 1997, Jason Flom, head of Lava Records, attended one of Kid Rock's performances, and met with Kid Rock, who later gave him a demo containing the songs "Somebody's Gotta Feel This" and "I Got One for Ya", which led to Kid Rock signing with Atlantic Records.By this time, Kid Rock had fully developed his stage persona and musical style and wanted to make a "redneck, shit-kicking rock 'n' roll rap" album, resulting in his fourth studio album, Devil Without a Cause, recorded at the White Room in Detroit and mixed at the Mix Room in Los Angeles.In 2001, Kid Rock filed a lawsuit to gain full control over the Top Dog record label, resulting in his receiving full ownership of the label in 2003.
The same year, Kid Rock contributed to the tribute album I've Always Been Crazy: A Tribute to Waylon Jennings, honoring the late country singer by covering the song "Luckenbach, Texas" in collaboration with country singer Kenny Chesney.
Noting that local rapper Esham was paid $500 to appear on ICP's album, Violent J claims that Kid Rock demanded $600 to record his guest appearance, alleging that Esham and Kid Rock had a feud over who was the bigger rapper.
Later in the year, Kid Rock recorded the EP Fire It Up at White Room Studios in downtown Detroit, run by brothers Michael and Andrew Nehra, who were forming the rock-soul band Robert Bradley's Blackwater Surprise.
In November, Kid Rock released his fifth studio album, Cocky.
The album became a hit, spurred by the crossover success of the single "Picture", a country ballad featuring Sheryl Crow which introduced Kid Rock to a wider audience and was ultimately the most successful single on the album.
By 1994, Kid Rock's live performances had mostly been backed by DJs Blackman and Uncle Kracker, but Kid Rock soon began to utilize more and more live instrumentation into his performances, and formed the rock band Twisted Brown Trucker. Clark, the producer discovered that Kid Rock could sing when he recorded a reworked cover of Billy Joel's "It's Still Rock and Roll to Me", entitled "It's Still East Detroit to Me", which Clark claims led him to encourage Kid Rock to sing more.