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As David Letterman prepares to host his last installment of The Late Show May 20, Randy Houser is looking back on the big break the host gave him back in 2008.

Before he became a regular at #1 on the country charts, Randy was struggling to break through with his emotional debut single, “Anything Goes.” Letterman heard the song while working on his ranch, loved it, and booked Randy to perform a special version of the song on The Late Show.

Randy tells Rolling Stone, “He loved the second verse of the song so much he wanted to hear it twice. The arrangement was literally in Dave’s request. ‘Anything Goes’ was the first single I ever put out, maybe in the fifties on the chart at the time.”

Letterman is known for taking a chance on new artists, as he did recently booking country newcomer Chris Stapleton to perform on The Late Show.

Randy says of Letterman’s music booking approach, “It doesn’t have to be a big hit — if Dave digs it, he pushes it.”

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