Which artist was the first to win five Grammys in a single night?

Roger Miller was the first artist to win five Grammys in a single night, achieving the feat at the 1966 Grammy Awards.

Miller’s awards reflected his unusual blend of country, pop, and novelty songwriting. He won for recordings connected with “King of the Road,” “Dang Me,” and his album The Return of Roger Miller. His witty phrasing and distinctive delivery made him one of country music’s most recognizable performers of the 1960s.

The five-award total was a major Grammy milestone because the ceremony was still relatively young. Later artists surpassed it, including performers who won six, eight, or more awards at one ceremony.

Miller’s record is sometimes confused with later single-night records because the number of Grammy categories and competitive fields changed over time. His achievement belongs to the 1966 ceremony and was the first five-award sweep.