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40 – Over the Rainbow – Harry Nilsson

Saint Harry, he had the voice of a broken angel. He kills this version of Dorothy’s ode to freedom and brings to it an even deeper level of tragic yearning.

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I'm a writer/editor with a penchant for saddle shoes, pontification and fried pork rinds. Equal parts gadfly, cut-up, provocateur, philosopher, and silly-willy. My personal heroes include Reggie Jackson, Elvis Costello and Philip Roth.


  1. Kudos for admitting the “uncool” Carpenters delivered a stone-cold classic with “Superstar.”

    May I suggest “2000 Miles” by The Pretenders? Gut-wrenching enough to sap anybody of their holiday spirit.

  2. “Angel Eyes ” by Frank Sinatra is probably the greatest song about lost love and an anthem to his break up with Ava Gardner. The finest last line ever ” Excuse me while I disappear “

  3. Prefab Sprout: “We Let the Stars Go”
    Laura Nyro: “Christmas in My Soul”
    And anything from the Wild Child album by Savage Rose is guaranteed to rip your heart out of your chest, stomp on it a dozen times then stick it back in the wrong way with chunks of gravel stuck to it.

  4. This list is pure shit. Most of the songs I can’t even peg, and I’m 52 and have been a music fanatic musician for most of that time.

    • Any list constructed of sad songs that gjves country music short shrift is like trying to build a bridge with pudding. George Jones’s She Stopped Loving Her Today, and George Strait’s I Can Still Make Cheyenne are just two that would skyrocket to the head of this class of mostly pop mush.

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