“Paperback Writer” is probably one of the more famous ones. (Thanks, Jeopardy!)
Don’t Cry Joni (1975) by Conway Twitty and Joni Lee.
Yabbut I don’t know the lyrics.
There’s also a 1937 song, Having A Wonderful Time (Wish You Were Here).
Letter to Hermione,* from David Bowie’s “Space Oddity”** album.
*Links to YouTube video.
**Also called “Man of Words/Man of Music” but originally titled “David Bowie,” not to be confused with the original album originally titled “David Bowie.”
Don’t forget Dear Mr. Jesus.
Tie a Yellow Ribbon is mostly the letter a prisoner sends to his wife before being released, it’s only the last couple of lines that reveal the results of that letter.
It’s not tactful, it’s not sympathetic, but it’s a letter.
And then there was the song popular about 50 years ago whose name I forget and who lyrics I just barely remember, but it was supposedly written by a grammar freak to his girlfriend and all the punctuation was sounded out, eg. “Sweet Heart semi-colon I love you exclamation point Some day comma in the future comma…”
Rod Stewart’s “You Wear It Well” is supposed to be a letter he’s writing to an ex-girlfriend, while on a break at work.
“Dear Eloise, I am writing to say
A number of funny things I heard today.
I heard that he’s left you and gone off to sea.
Could be the best thing that’s happened to me.”
- The Hollies, "Dear Eloise
The chorus of Jim Croce’s “Box Number 10” is a series of letters from a struggling musician, asking his parents for money.
As I write this letter
Send my love to you
Remember that I’ll always
Be in love with you.
“A Letter to Elise” by the Cure is really good.
We Love You, Call Collect by Art Linkletter (who is still alive at age 96!) was dedicated to his daughter Diane, who jumped out a window and died, supposedly while high on LSD.
Also, Living Colour’s Open Letter (To A Landlord).
“Gabriel’s Letter/My First Woman” from the musical Kiss of the Spider Woman is split between the character Valentin reading a letter from his unrequited love and Molina recalling his first sexual experience.
There are a couple of other songs from the musical that sound like letters, “Dear One” and “You Could Never Shame Me,” but I haven’t seen the show and I can’t tell from Wikipedia’s plot summary.
Isn’t Unchained Melody supposed to be a letter from a guy in prison?
I’ve always assumed For Emily, Wherever I May Find Her is a letter just based on the title.
Eliza Gilkyson has a song “Jedidiah 1777” on her album Paradise Hotel that deals with man’s letters home during the American Revolutionary War. I like the song and the background story makes it even more interesting.
From the site: ’ “Jedidiah 1777” tells of Gilkyson’s ancestral grandfather, Brigadier General Jedidiah Huntington, who fought alongside George Washington in the American Revolutionary War. Over a simple and relentless acoustic pattern, she sings, in dry matter-of-fact tones, lyrics that come directly from Huntington’s own letters to his family—letters she found at a Connecticut Historical Library. It’s an engrossing song that could have achieved something approaching epic status had Huntington been a more prolific correspondent.’
Tom Waits’ song Christmas Card From A Hooker In Minneapolis is in letter form.
“Letter to Dana” by Sonata Arctica
“Dear John Letter (To the Devil)” by Keith Green
Brad Paisley - Letter to Me
I lied, earlier. Jim Croce’s “Box Number 10” features a series of collect phone calls to his parents, not letters.
South of Cincinnati - Dwight Yoakam
The chorus is an unsent letter from a woman to her ex.