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Rapper Cowboy Troy exploded onto the country music scene in 2004 with a blend of country and rap he likes to call "hick-hop." It was his appearance on the Big & Rich track "Rollin' (The Ballad of Big & Rich)" that put him on CMT and into every honky tonk DJ's record collection that year, but Troy's involvement in country music and with Big & Rich began over a decade earlier. It was 1993 in his hometown of Dallas when Cowboy Troy — real name Troy Coleman — first met John Rich. Rich was then a member of Texassee, the band that would morph into Lonestar. Troy had grown up on Jerry Reed, Charlie Daniels, and the Oak Ridge Boys, but he also loved the rock of Kiss and ZZ Top and the hip-hop of Run-D.M.C. and Sir Mix-A-Lot. He found a friend in Rich, someone who was also based in country but a fan of all types of music. The two kept in touch as Rich took Lonestar to the top.
By 1999, Troy was asking for time off at his job managing a Foot Locker and heading to Nashville to shop his rap-meets-country demos. Rich was now working with Big Kenny and the two were busy hosting their "Muzik Mafia" nights — a performer's roundtable known for its risk-taking attitude. Troy's style fit right in and he spent the next three years perfecting his live show. He was more than ready when Big & Rich asked him to appear on their debut album. Horse of a Different Color became a massive hit and the sold-out tour that accompanied it included a showstopping appearance from Cowboy Troy. Performing "Rollin' (The Ballad of Big & Rich)" with the duo on the 2004 Country Music Association Awards made Troy only the second black artist to take the stage at the show, the first being Charley Pride 38 years earlier.
Cowboy Troy soon landed his own record deal with Warner Bros. Nashville and got to work on his debut with Big & Rich as producers. Loco Motive hit the shelves in May of 2005 as its first single, the rousing "I Play Chicken with the Train," was climbing the charts. He soon landed a gig as co-host of CMT's singing competition Nashville Star, which put him next to Wynonna Judd on one season, Jewel on the next. In 2007 he released his second full-length, the much more serious Black in the Saddle. A year later he performed at the Republican National Convention and parted ways with Warner Bros. His 2009 album, Demolition Mission: Studio Blue Sessions, landed on the indie label Winding Road. Demolition Mission did well enough to return Troy to the good graces of Warner Nashville, which put out his third album, King of Clubs, in spring of 2014.