More Seekers, more Judith:
Here is one excellent goodbye song - more of a happy breakup song really - by the Mavericks.
Amanda McBroom - Errol Flynn
Mary Chapin Carpenter - Only a dream Sarah McLachlan - Angel Eleanor McEvoy - Only a woman's heartDaffodil Lament – by The Cranberries
Because it paints the dismal emptiness you can feel when you realize you’re in a dead relationship, and the incredible lightness you feel when you’re free.
It’s A Dream – by The Nuns
For a less voluntary ‘goodbye’. Because it’s a sucker punch when you grok “It’s the saddest thing I’ve ever seen” is just another way of saying “I never cry harder”.
“When you call my name and you’re not there, it’s the saddest thing I’ve ever seen.” That’s a wishful daydream, an impossibility, therefore a nightmare, and the saddest thing.
“I Can’t Make You Love Me If You Don’t” by Bonnie Raitt
“Help Me Make It Through the Night”, many artists, I’ll go with Sammi Smith
“By the Time I Get to Phoenix” by Glen Campbell
“Neither One of Us Wants to be the First to Say Goodbye” by Gladys Knight and the Pips
“Here Comes Goodbye” by Rascall Flatts
Fleetwood Mac: ‘That’s alright’ ‘Gypsy’
Third Eye Blind: ‘How’s it going to be’
Thought of another one. “I Will Always Love You”. Both the Dolly Parton and Whitney Houston versions are good.
“Goodbye Francine” written by me. It’s the first song I ever wrote, that I perform with current band, about being kicked out of my previous band.
(my current bandmate has a great saying - “I’ve been kicked out of more bands than you’ve been in”)
Life, and Death.
"Bright eyes, burning like fire Bright eyes, how can you close and fail? How can the light that burned so brightly Suddenly burn so pale?"Jerry Jeff’s Jaded Lover.
*But we would never agree if we talked all night
Things are gettin’ heavy, I’m traveling light
Goodbye jaded lover you undercover queen for a day
*
Bonnie Raitt’s Opening Farewell
There’s a train every day
Leaving either way
Thanks for getting me all teary-eyed during breakfast, MarvinHomba! 
Saddest of all - When She Loved Me.
See also A Boy and His Frog - a farewell to Jim Henson.
Regards,
Shodan
All guitar lovers need to check out the Tedeschi Trucks Band cover this one, there are several blistering versions available on YouTube.
I’ll see you and raise you Old and Wise, also by the APP. Brings a tear to my eye every time I hear it.
Already some great ones listed. Here are a couple:
Fleetwood Mac - Go Your Own Way
Sanford Townsend Band - Smoke From a Distant Fire
I think this more-or-less qualifies: He Stopped Loving her Today by George Jones:
The Power of Goodbye by Madonna:
Two suggestions, with different feels:
First, there’s Willie Nelson’s deeply messed up “I Just Can’t Let You Say Goodbye”, which starts off plaintive and ends up Jesus Christ Dude:
Then there’s the classic Doo-Wop song, “One More Minute”:
An excellent choice!
I’ll add that FC’s “Farewell, Farewell” is equally touching and beautiful. It was written by Richard Thompson after his GF was killed in a vehicle accident. I had this played at my wife’s funeral.
I saw this thread and immediately thought of Springsteen’s “Bobby Jean.” It’s not a great song, but is probably more upbeat about good-byes than most.
Speaking of Bobby’s…What about Me and Bobby McGee?
Could be. I suspect most “goodbye songs” could be interpreted that way. Probably because all goodbyes have an evocation of death in them anyway. That’s why they’re so poignant.
Another one that I don’t think I saw yet in this thread: The Only Living Boy in New York.
“Tom get your plane right on time. I know you’re gonna be fine”
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