There's no shortage of sad songs about rainy days and lovers who don't bring flowers. And then there are songs that truly bring the pain -- songs so despairing they can make us wonder why we even bother.

№5

The Smiths (1986)
The Breakdown: For Morrissey, the world's loneliest singer, life isn't just over -- it never really began.
The Waterworks: "As I climb into an empty bed/Oh, well, enough said."
Casualty Count: One lonely soul ... any minute now.

№4

'Hurt'
Johnny Cash (2002)
The Breakdown: In failing health, the great American singer tolls a death knell for the rest of us with this brutal Nine Inch Nails song about addiction and self-destruction.
The Waterworks: "And you could have it all/My empire of dirt/I will let you down/I will make you hurt."
Casualty Count: Everyone he knows ("goes away in the end").

№3

The Breakdown: The cute Beatle writes a timeless, devastating ode to the futility of life, set to a grieving string octet.

The Waterworks: "Eleanor Rigby died in the church and was buried along with her name/Nobody came."

Casualty Count: One spinster, one pair of socks.

№2

The Breakdown: The Queen of Soul-Sapping is haunted about losing a loved one.

The Waterworks: "Angels have no thought of returning you/Would they be angry if I thought of joining you?"

Casualty Count: One woman's will to live.

№1

The Breakdown: Breathy Massachusetts sad sacks offer a lovely ballad about a woman choking to death on exhaust fumes ... and a cloud of minor chords.

The Waterworks: "They found her car/Still running/In the garage."

Casualty Count: One woman, and the drink she was holding.

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