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3. The Time He Recorded A Duet With Willie Nelson

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3. The Time He Recorded A Duet With Willie Nelson | Country Music Videos
Photo credit: TobyKeithVEVO YouTube Channel
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When you record a duet with Willie Nelson, it's an automatic indication that you are a force to compete with. Such is the case for Toby, who recorded a duet in 2003 with the iconic country outlaw. 

Called "Beer for My Horses," the song remains one of Toby's longest-lasting number one hits of all time. The song topped the charts for a total of six weeks, which also made Willie the oldest artist to ever top the country charts (he was 70 at the time).

Following the success of their duet, Toby took it one step further by writing and starring in a film of the same title. Released in 2008, the film featured Toby in the lead role as deputy sheriff Joe Bill "Rack" Racklin. Toby and Willie also starred in the song's epic music video, which won Video of the Year at the ACM Awards.

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