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Outlaw, unlike Chesnutt's previous work, is composed of covers of some 'Outlaw Classics'. The album includes material from Billy Joe Shaver, Willie Nelson, Kris Kristofferson and Waylon Jennings. Chesnutt said “When I was first approached to record this CD, my reaction wasn’t just ‘yes,’ but ‘hell, yeah. I cut my teeth on this kind of music, and it’s an opportunity for me to pay tribute to some of my biggest heroes in country music.” Producer Pete Anderson commended Chesnutt on the work he did with the record by saying “Mark Chesnutt put on a vocal display like I’ve never before seen in the studio. He stood in front of the mic and sang the whole record, from beginning to end, flawlessly . We are all amazed at the results. There may be singers out there as good as Mark, but there are none better and, at this point in my career, I am thrilled to have had the opportunity to work with this caliber of talent.”