25 Songs for Saying Goodbye

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An acquired taste to say the least, Daniel Johnston’s lo-fi music is actually quite amazing if you can penetrate his idiosyncratic voice and delivery. A visionary artist of the highest order, Johnston delivers “Go” as a blessing to a friend who’s found his true love. “So you think you’ve found the one/And she knows just how you feel/And you say that she’s for real and she’s fun/Well, that’s all well and good/That’s just the way it should be/To understand and be understood is to be free/So I think that you should go/Go on ahead/Take her in your arms and be wed.”

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Another song about the dissolution of a relationship sung with heartfelt emotion that only someone of Jeff Buckley’s talent can pull of so brilliantly. “Kiss me, please kiss me/But kiss me out of desire, babe, and not consolation/You know it makes me so angry cause I know that in time/I’ll only make you cry, this is our last goodbye.”

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Steve Earle is a powerhouse performer, especially in his post-prison, heroin addiction days. On “Goodbye,” taken from Earle’s 1995 comeback album, Train ‘A Comin’, the feelings of regret and resignation are palpable. “I remember holdin’ on to you/All them long and lonely nights I put you through/Somewhere in there I’m sure I made you cry/But I can’t remember if we said goodbye.”

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This song is a hoot, and even though it takes place just after the leaving, it still makes the list for its playfulness. Sung as a conversation between ex-lovers (with Jarvis Cocker of Pulp handling the male role), it’s a great fuck-off song. “Well, I’ve been in heaven since I walked away/I never thought that I could feel as great as I do today/’Cause you were nothing but a waste of space/And life is wonderful now that I’m over you.”

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Opening the track with the spoken line “this little song is for Fred” tells you right off the bat that this farewell reel is an elegy to Smith’s recently departed husband, Fred “Sonic” Smith, who died just two years earlier. “A powerful farewell indeed, one that is guaranteed to jerk a tear or two. So darling farewell/all will be well/and then all will be fine/the children will rise/strong and happy be sure/cause your love flows/and the corn still grows/and God only knows/we’re only given/as much as the heart can endure.”

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An honest, direct and forceful farewell to a no-good guy, Fiona Apple’s venemous directive is steeped in anger and bitterness. It’s music to my ears! “How many times do I have to say/To get away-get gone/Flip your shit past another lass’s humble dwelling.”

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You can’t have a list about saying goodbye without “Leaving on a Jet Plane.” I just couldn’t bring myself to including John Denver’s original version. Instead I opted for Tarnation’s hazy cover, which still delivers the sadness of leaving your lover. “So kiss me and smile for me/Tell me that you’ll wait for me/Hold me like you’ll never let me go/’cause I’m leavin on a jet plane/Don’t know when I’ll be back again/Oh babe, I hate to go.”

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The 6ths is one of the many side projects of Magnetic Fields’ leader, Stephen Merritt, so you know this one will be a melancholy gem. Add electro-pop pioneer, Momus, and you have a real treat. “Let the poets struggle to describe your heart/Your art of love and your love of art/Well, if you ever loved me/Tell me so/As you turn to go.”