In 1980 Clint Eastwood sang a song with Merle Haggard called "Bar Room Buddies."  It was off the soundtrack to a movie at the time called "Bronco Billy."   That soundtrack also included a number one hit from Ronnie Milsap called "Cowboys & Clowns."  Not only did Clint sing with Merle Haggard, but he also did a duet once with Ray Charles.

Here's his number one hit with Merle Haggard, "Bar Room Buddies."

And of the "Any Which Way You Can" soundtrack "Beers To You" with Ray Charles.

Clint Eastwood was a huge fan of country music and included mostly country in his movie soundtracks.  Who knew he could sing, too?

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