Nelson released only one single at Monument before signing with RCA in 1964. At his first RCA session, November 12, 1964, he recorded his version of “Pretty Paper” along with “What a Merry Christmas This Would Be” written by Hank Cochran and Harlan Howard. Some of the musicians on the session would become stars in their own right, including Jerry Reed, Ray Stevens, pianist Hargus “Pig” Robbins, and Ray Walker of the Jordanaires. Robbins and Walker went on to become members of the Country Music Hall of Fame. The session was produced by future Hall of Fame member Chet Atkins.
Nelson’s version of “Pretty Paper” was rush-released by RCA for the 1964 holiday season but failed to chart. The single was re-released in 1966, but met the same fate as before. The recording, which had been available only on a 45 rpm record, made its way onto some RCA Victor Christmas compilation albums.Much of Willie Nelson’s recorded output during the late 1960s and early 1970s went unnoticed, but success was just around the corner. In 1975, Nelson finally struck gold at Columbia Records with the album Red Headed Stranger and the hit single “Blue Eyes Crying in the Rain.” In country music’s outlaw era, Nelson became a superstar. There was renewed interest in some of his older recordings, and many were reissued by his previous labels, including RCA. Radio stations began to play Nelson’s 1964 version of “Pretty Paper,” and it eventually became a holiday classic.
Nelson re-recorded “Pretty Paper” in 1979 for Columbia, but the version recorded for RCA (at the studio now known as Historic RCA Studio B) has become a fan favorite and is heard each December. The song has been covered by artists including Kenny Chesney, Glen Campbell, Chris Isaak, Carly Simon, and Randy Travis.