Earth Class Mail

A Letter Is Worth 1,000 Songs - The 10 Best

By John Horton, Contributor @ Earth Class Mail

You can say a lot with a letter, and even more when you add a soundtrack to it. These ten just happen to be the ones I think do it best. Some are fun, some satirical, and some are downright emotional. 

10. An Open Letter to NYC (Beastie Boys) 

“Dear New York, this is a love letter,” rappeth Mike D. And a love letter it is.

This track appears on To the 5 Boroughs, their first album post 9/11. In the song, they give love to all five boroughs – Manhattan, the Bronx, Queens, Brooklyn, and Staten Island. 

“Dear New York, I know a lot has changed/ two towers down, but you’re still in the game.”

I know a lot of artists have made songs about staying strong post 9/11, but for me, the Beastie Boys do it best. 

9. Strawberry Letter 23 (The Brothers Johnson)  

Strawberry letters 1-22 are better left as journal entries, but Strawberry Letter 23! The public needs to hear. 

It’s got a plucky disco thing going on, and it’s probably one of those songs you know, but you don’t know where from. That’s because it’s been sampled and covered extensively, and for great reason.

This is a strut down the street song – a head wobbling confidence booster, if you will. I would, if I were you.

8. Christmas Card from a Hooker in Minneapolis (Tom Waits)

Suspiciously hipster though it is, my number 8 slot goes to Tom Waits’ Christmas Card from a Hooker in Minneapolis. It’s a prime example of a song-title’s value, because I don’t remember a damn thing about the song itself. 

But that title! 

It’s really all we need to know. Fishnets. Snow. A lipstick smooched postcard. You get me Hype Williams on the phone, I’ll get you a music video. 

Actually, I am a Tom Waits fanatic. The guy delivers art in a singular way. His style is all his own, yet you hear the jazz, the rock, the gospel, the blues – all of which result in the voice of a uniquely American growler. Always worth a listen. 

7. Please Mr. Postman (The Marvelettes)

Where’s Marty McFly? Where’s the diner? Where’s the Porkpie hat? This jukebox hit is yesteryears version of an unresponsive texter (how could you be so cold).

She’s waiting “so patiently, for just a card, or just a letter” from her booface. She doesn’t know where’s he’s been, so if you have any information, please contact the local authorities.

This is a good starter song on YouTube, if you want some upbeat music to play while you and your kids clean the house, or if you want to scream at them and not have the neighbors hear.

6. Signed, Sealed, Delivered I’m Yours (Stevie Wonder)

The King amongst Kings, Stevie Wonder. This is a cross generational hit that gets played everywhere from bat mitzvahs to Chinese New Year parties.

Stevie Wonder is that rare combination of extremely-talented musician and astounding lyricist. If it was possible to trademark a sound, you could say Stevie is the owner of “yooowwww” and “ahhhhhh.” His music is up tempo and emotional. Easily a top-tenner on many lists.

5. I’m Gonna Sit Right Down and Write Myself a Letter (Fats Waller)

If this song isn’t rolling over the opening credits of a Woody Allen movie somewhere, I’ll be disappointed. This American standard has been recorded by powerhouses like Nat King Cole, Frank Sinatra, and Paul McCartney just to name a few.

I almost feel like I’m at a lemonade stand when listening – like a Penny-farthing is cruising by in the background; like Mrs. Walden is tugging on the ear of her rabble-rousing son Tommy for throwing cherries at passing cars.

Of course, the song is really about a guy writing a letter to himself and pretending it came from someone else. 

4. Stan (Eminem)

Ever catch yourself nodding along to a song, mouthing lyrics about kidnapping and murder? You’ve most likely stumbled into Eminem’s reverie, Stan.

It’s a greasy, grimy toe-tapper that successfully nuzzles itself into its themes of isolation and detachment. The sampling of Dido’s song Thank You is one of the best in hip hop history, adding a powerful but suppressed beauty. 

Little known fact – this song is directly responsible for an uptick in celebrity replies to fan mail. That’s what my uncle told me, anyway.

3. The Letter (The Boxtops)

First of all, watch this live performance of the song so you can see Alex Chilton’s uncomfortable death stare as he sings. The whole band has this restrained groove thing going.

Kind of apropos for the time, I guess. It’s like their manager said, “No matter how poppy the song sounds, I better not see anyone dancing.”

I absolutely love this song. It’s catchy as hell and I dare you to listen without tapping your foot. This is blue-eyed soul at its best. Put this song on in front of your aunt and I guarantee you she’ll start doing the Mashed Potato. 

2. Mailman (Soundgarden)

No list is complete – scratch that – no list should exist without a Soundgarden song. “But John!” you say, notionally, “What about a country music list? Surely Soundgarden couldn’t exist there!”

I refer you to the above song, where, if you’d please, you will hear a clearly yodeling Chris Cornell. But I digress.

Mailman rocks your damn socks off. I was confused at first why it’s called “Mailman”, but then I realized he’s singing “I’m writing you all the way,” and not “riding you all the way.” Kind of makes a difference.


1. Death Letter Blues (Eddie James “Son” House)

This is quintessentially American music, and a damn fine representative if you ask me. Although I first heard this as covered by the White Stripes (also worth a listen), this song comes from the dustiest era the U.S. mail has ever seen, the 1920’s.

Death Letter is the lament of a man who receives news of his estranged love’s death. Son House’s unrestrained vocals and swift strumming guitar betray the sound of a man familiar with pain and suffering.

His twang is what your mind hears when you think Mississippi Delta.

His legacy was nearly lost to the Great Depression, but he was “rediscovered” during the 1960’s American folk music revival, and is deservedly recognized as a blues legend.

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