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“Hit the Road Jack” is a song written by rhythm and blues artist Percy Mayfield and first recorded in 1960 as an a cappella demo sent to Art Rupe. The recording hit number one for two weeks on the Billboard hot 100 beginning on Monday, October 9, 1961. It won a Grammy award for best rhythm and blues recording; the song was number one on the R&B chart for five weeks becoming Charles’s sixth number one on that chart.