“I’m Gonna Sit Right Down and Write Myself a Letter” is a 1935 popular song with music by Fred E. Ahlert and lyrics by Joe Young. It has been recorded many times, and has become a standard of the Great American Songbook. It is one of several songs from the Harlem Renaissance featured in the Broadway musical Ain’t Misbehavin’.
The song was recorded by Frank Sinatra for his 1954 album Swing Easy, Bing Crosby for his 1957 LP Bing with a Beat and again by Sinatra in 1962 for his collaborative album with Count Basie, Sinatra–Basie: An Historic Musical First.
The song had a major revival in 1957 in a recording (on April 3) by Billy Williams with orchestra directed by Jack Pleis. It reached #3 on the Billboard magazine charts. A reported million-seller, it was awarded a gold record.
Charlie Gracie (mostly known for his 1957 #1 hit “Butterfly” on Cameo Record label #105—45rpm) recorded “I’m Gonna Sit Right Down and Write Myself a Letter” (Cadillac Record label #141—45 rpm). The flip side of the record was a song written by Gracie, “Boogie Woogie Blues”.
Among other versions are recordings by Nat “King” Cole, Scatman Crothers, Gregory Isaacs, Barry Manilow, Dean Martin, Anne Murray, Willie Nelson, Linda Scott, Shakin’ Stevens and Sarah Vaughan. Bill Haley & His Comets recorded a rock and roll version of the song in 1957. Fabian recorded his version of the song in 1960 on Chancellor Records. In 1974 Cleo Laine included the song as her opening song on the album I Am a Song and sang on stage during her subsequent tour. New Jersey entertainer Uncle Floyd (aka Floyd Vivino) has covered this song in his live performances.
Madeleine Peyroux also covered this song on her debut album Dreamland (1996). In 2012 Paul McCartney covered it on his album of standards, Kisses on the Bottom and chose one of its lines as the title.