I'm Gonna Sit Right Down And Write Myself A Letter
Frank Sinatra and Basie Lyrics

The song "I'm Gonna Sit Right Down and Write Myself a Letter" was written by Fred E. Ahlert and Joe Young and was first recorded in 1935 by Fats Waller. The lyrics describe a person who is missing someone special and decides to write a letter to themselves, pretending that it came from the person they miss. The song was later covered by many artists including Frank Sinatra and the Count Basie Orchestra.

The lyrics depict a combination of loneliness and hopefulness as the singer longs for someone special but is unable to reach out to them. The act of writing a letter to oneself is a way to cope with the absence of the loved one and to imagine what they might say in response. The imaginary letter is filled with "oh so sweet" words and kisses at the bottom, providing some emotional relief to the singer. The use of the phrase "I'll be glad I got 'em" suggests that the singer is holding onto the hope that the imagined affection from the letter will give them comfort.

The second verse continues to describe the imaginary letter, with the singer wishing the other person well and signing off with "love" just as they might in a real letter. The repetition of the line "I'm gonna sit right down and write myself a letter" emphasizes the singer's sense of determination to find a way to connect with their loved one, even if it is only in their own imagination. The final line "Although it's not the same, I'll make believe it came from you" highlights the bittersweet nature of the song, in which the act of writing a letter to oneself is a solitary and incomplete substitute for true communication with the person one longs for.