I find these songs depressing to varying degrees--your mileage may vary:
Johnny Cash - "Hurt"
Chely Wright - "The Love He Left Behind," "She Went Out for Cigarettes," "The Love that We Lost," "Before You Lie," "Her," "The Other Woman," "The Last Supper"
Mandy Barnett - "I've Got a Right to Cry"
Audioslave - "Getaway Car"
The Corrs - "Only When I Sleep," "Old Town," "Love to Love You," "Little Wing"
Three Day Grace - "Home"
Theory of a Deadman - "The Last Song"
Johnny Cash - "Hurt"
Chely Wright - "The Love He Left Behind," "She Went Out for Cigarettes," "The Love that We Lost," "Before You Lie," "Her," "The Other Woman," "The Last Supper"
Mandy Barnett - "I've Got a Right to Cry"
Audioslave - "Getaway Car"
The Corrs - "Only When I Sleep," "Old Town," "Love to Love You," "Little Wing"
Three Day Grace - "Home"
Theory of a Deadman - "The Last Song"
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