"The First Cut Is the Deepest" is a 1967 song written by Cat Stevens, originally released by P. P. Arnold in May 1967. Stevens' own version originally appeared on his album New Masters in December 1967.
Stevens made a demo recording of "The First Cut Is the Deepest" in 1965, but originally hoped to become a songwriter. He wrote the song earlier to promote his songs to other artists, but did not record it as his own performance until early October 1967 with guitarist Big Jim Sullivan, and it did not appear until his second album, New Masters, was released in December 1967. He sold the song for £30 to P.P. Arnold, and it became a huge hit for her, as well as an international hit for Keith Hampshire, Rod Stewart, and Sheryl Crow. The song has won Stevens songwriting awards, including two consecutive ASCAP songwriting awards for "Songwriter of the Year" in 2005 and 2006.
Keith Hampshire had the first chart-topping hit of the song when his recording of it became a number one hit in Canada in 1973, reaching the top of the RPM 100 national singles chart on 12 May of that year. It also topped the Canadian Adult Contemporary chart. This recording also charted in the US, albeit outside the top 40.
Music & Media wrote about the song: "Dee-lightfully our Swedish Papa tackles the old Cat Stevens hit in a pop dance-infused reggae style with a snappy ragga interlude. Radio, club and dub edits are
Sheryl Crow's version of "The First Cut Is The Deepest" is the first single released from her 2003 compilation album The Very Best of Sheryl Crow. It became one of Crow's biggest radio hits, remaining 36 weeks in the Billboard Hot 100, and was also Crow's first Top 40 solo country hit, following the success of her hit duet with Kid Rock, "Picture". The song topped the airplay charts in the US and became a platinum seller, also reaching No. 14 on the Billboard Hot 100 singles chart and went to number one on the AC chart for two nonconsecutive weeks.