Before even completing his graduation, he took up work at an oil rig. However, unfortunately, he lost his little finger in an accident while opening a bucket with a knife. Unperturbed, he asked the doctor to join the finger in such a way that he could continue playing the guitar.
He spent the early years of 1990s playing in the honky tonk bars in and around Nashville, Tennessee. It was during these years that he was spotted by an executive of Capitol who signed him to the label.
Year 1996 was a breakthrough one for this talented musician as he made a debut with his single, ‘There’s a Girl in Texas’. The song was a major hit and topped the Billboard Hot Country Singles & Track charts at the 20th position.
Following the super success of his debut song, he released his debut album ‘Dreamin’ Out Loud’ later in 1996. The album replicated the success of his debut song track as it became a super hit with his singles reaching the number 1 status.
Inspired by the success of his debut album, he released his second venture, titled, ‘Big Time’. Except for a single track, ‘The Rest of Mine’, which reached the Top 5 position, the album could not carry forward the super success his previous album had achieved.
In 1999, he released his third album, ‘More…’. The fate of the album was much like its predecessor, except the title track and the album failed to achieve the gold status.
Following an accidental mishap, he released his fourth album, ‘Chrome’ in 2001. It became the first album to reach the Top 5 status on the country album charts with its title track being listed in the Top 10.
He followed this up with two albums in 2003, a Greatest Hits collection and ‘Comin’ on Strong’. While the former produced one single ‘Then They Do’ the latter produced two, ‘Hot Mama’ and ‘rough & Ready’ both of which peaked at No 5 and No 13.
In 2003, he did voiceover for a commercial series for KFC. He even made his debut in television starring in the role of Big John for the television series, ‘King of the Hill’. He also made an appearance on ‘Hollywood Squares’
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In 2004, he starred as Curtis, a prison convict in the television series, ‘Yes, Dear’. Additionally, he played the character of Elvin Mackleston in the series, ‘King of the Hill’.
Going back to his singing career, in 2005, he released the album, ‘Songs About Me’. While its first single, ‘Arlington’ created controversy, its second single, ‘Honky Tonk Badonkadonk’ became a huge crossover hit. For the first time, his song was featured in the Top 40 of the Billboard Hot 100.
In 2005, he starred in three television series, ‘Higglytown Heroes’, ‘Blue Collar TV’ and ‘My Name is Earl’.
Year 2006 witnessed the release of his seventh studio album, ‘Dangerous Man’. While the first single, ‘Swing’ peaked at No.20, the second ‘Ladies Love Country Boys’ became the Number 1 single on the country charts. This was the second time after the 1997 released single ‘No Thinkin’ Thing’ that his song reached the number one status.
In 2007, he came up with the single, ‘I Got My Game On’ the song, supposedly to be the flagship song of a new album, instead became the lead track for his second Greatest Hits compilation, ‘American Man: Greatest Hits, Vol. 2’.
He then released the second single from the album, ‘You’re Gonna Miss his’. The song reached the number one status on the Hot Country Songs and became the fastest climbing single of his. It furthermore, went on to enlist itself at the Top 12 in the Billboard Hot 100 and Top 19 in the Billboard Pop 100. At the Hot Digital Songs track, it peaked at number 8.
In 2007, he released his first book, ‘A Personal Stand: Observations and Opinions from a Free Thinking Roughneck’.
In 2008, he starred in the big screen, playing the role of ‘The Man’ in the film, ‘Trailer Park of Terror’ and Angel of Death in ‘An American Carol’. He also starred in one of the episodes of the television series ‘The Young and the Restless’.
From 2008 to 2011, he starred in 16 episodes of the television show, ‘Celebrity Apprentice’. In the first season, he played as a celebrity contestant finishing off 2nd.
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In 2008, he released the single, ‘Muddy Waters’ from the album ‘X’. The album included the Top 20 hits ‘Marry for Money’ and ‘All I Ask For Anymore’, both of which peakedat No. 14.
In 2010, he left Capitol Nashville to sign a contract with Show Dog Universal Music. His first song from the label, ‘This Ain’t No Love Song’ was released in May 2010. The song typified as the head track for his subsequent studio album, ‘Cowboy’s Back in Town’. The album debuted at the No 54 position on the charts.
In 2010, he came up with his third compilation album, ‘The Definitive Greatest Hits Til’ The Last Shot’s Fired’. He has also sung the National Anthem at Dallas Cowboys Stadium. His films and television appearances include, ‘Lifted’, ‘Tough Trade’ and ‘Ace of Cakes’
In 2011, he came up with his tenth studio album ‘Proud to Be Here’. The same year, he starred in the film, ‘The Lincoln Lawyer’ as Eddie Vogel.
In 2013, he released two albums, ‘Love Will..’ and his first Christmas album, ‘The King’s Gift’. He also came up with his compilation album ‘Icon’. The same year, he starred as himself in the 12 episodes of ‘All Stars Celebrity Apprentice’ wherein he made it to the finals and ended up winning the same.