This song won the 1965 Grammy Award for Best Contemporary Rock 'N Roll Single, Best Contemporary Vocal Performance, Best Country & Western Recording, Best Country Vocal Performance, and Best Country Song. Talk about a cross-over! Singer-songwriter Roger Miller said during an interview: "I was doing a show in a place you have probably never heard of called Kitchener, Ontario, Canada, and I saw a statue of a hobo in a cigar shop were I was staying. I purchased it and took it to my room and wrote t

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