Leave-Taking: My Favorite Goodbye Songs

Saying goodbye is hard. In this life, leaving is painful and all-too-common. And as Plankeye sang in their amazing song, “Goodbye”, Death takes many forms. Even while alive. You move away from home. Someone you love moves to a new city. Or, even more difficult, the leaving is permanent; a loved one dies. In these times of leave-taking, I have often received blessing and consolation through music. Today, I want to talk about a few of my favorite goodbye songs.

Before we dive into the list, I need to thank fellow Rambler, Gowdy Cannon, for inspiring this article. Last week, he took us down memory lane to celebrate Hootie and the Blowfish’s landmark debut album, Cracked Rear View.” In that article, he mentioned an unreleased song called, “Goodbye” that has helped him process his current state of transitioning from a 17-year ministry in Chicago. That got me thinking about some of my favorite goodbye songs and this is the result.

As I have written before, music has a way of peeling back our defenses. At its best, music can say the things we are feeling. It can express our deepest emotions while at the same time providing comfort. I’m going to do my best to keep my words short here and let the music do most of the talking.

“I’ll Remember” by Madonna

“Bold strategy, Cotton. Let’s see if it pays off for him.”

Dodgeball: A True Underdog Story (2004)

Yes, I am starting off this list with a Madonna song. Yes, I am still a Christian. And yes, I do find much of her music and worldview problematic and/or offensive. But this song doesn’t fit those descriptors. “I’ll Remember” is a beautiful and melancholy pop song about saying goodbye to someone you love. The lyrics are vague enough that it could be about death or something less permanent, but there is a heartfelt sense of peace that permeates the song. It’s really quite lovely.

“Hear You Me” by Jimmy Eat World

A song about death that moves me every time I hear it. It’s what all good, emotional, rock and roll should sound like.

“Don’t Cry” by Adam Again

In the annals of Christian music, I doubt there has ever been a more devastating song about divorce. Perfecta, the album this song appears on, was built around the dissolution of Gene Eugene’s marriage to his band-mate, Riki Michelle. It’s raw and sometimes bitter but this closer adds a gentleness to it that is desperately needed.  

“I’ll Meet You There” by WhiteHeart

This song was instrumental in getting me through the very difficult time of leaving my home and all my friends when I moved away from Panama to start college. Seriously. I listened to this song a lot during that season of my life. In the pantheon of great goodbye songs, this is probably my go-to.

“I Grieve” by Peter Gabriel

The first half of this song is about as sad as I’ve ever heard. It’s heartbreaking stuff. But Gabriel transitions from that sense of overwhelming sorrow mid-song and turns it into a celebration of life. I don’t agree entirely with the beliefs of life and death expressed in this song, but that doesn’t take away from its power. We are more than the flesh and bones that tie us to the earth.

“In My Arms Again” by Michael W. Smith

Little known fact: Michael W. Smith submitted this song for the movie Titanic. It would have been his “My Heart Will Go On” of the movie if it had been chosen. I vastly prefer Smitty’s song to Celine’s, though I don’t hate hers in the least. This is a song of loss, longing, and love. Mr. Smith flat out kills it.

“Across the Miles” by Nouveaux

Here is another song that got me through my move away from Panama. I am unashamed to admit I listened to this 80s style power ballad with tear filled eyes more than once. If you have a lighter, this is the time to raise it high.

“Into the West” by Annie Lennox (The Return of the King Original Motion Picture Soundtrack)

This is the closing song to my favorite film trilogy of all-time – The Lord of the Rings. The song, inspired both by the book as well as a personal story of losing someone too young, strikes the perfect emotional tone to close out the series. It recognizes the pain and the loss we all feel but never loses sight of the hope beyond these shores.

“Streets of Gold” by NEEDTOBREATHE

I’ll end on a happier note. This wouldn’t even rank as one of NEEDTOBREATHE’s top 30 songs, but for very specific times, it is like the perfect medicine. The song, with no cheese factor, speaks to our eternal hope in Christ. We may say goodbye in the here and now but “one day, we’ll walk upon streets of gold.” Goodbyes get a little easier when we have that to hold on to.

Final thoughts

I would love to read about some of your favorite goodbye songs. Please, post them in the comment section below or on one of our social media platforms.

Phill Lytle
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Phill Lytle

Phill Lytle loves Jesus, his wife, his kids, his family, his friends, his church, J.R.R. Tolkien, C.S. Lewis, 80s rock, the Tennessee Titans, Brandon Sanderson books, Whiteheart, Band of Brothers, Thai food, the Nashville Predators, music, books, movies, TV, writing, pizza, vacation...

4 thoughts on “Leave-Taking: My Favorite Goodbye Songs

  • July 11, 2019 at 11:58 am

    Those kinds of songs are important. Humanity and eternity come together in our human experience. Thanks, Phill.

  • July 11, 2019 at 9:28 pm

    The Plankeye one is my favorite because it speaks most clearly to my recent Good bye referenced above. Hootie’s is a close second. Of those songs I know above, I appreciate them all.

    Others that I really like not listed above by Phill or me would be: Good Riddance by Green Day (Seinfeld connection helps), “How Can I Help You To Say Goodbye” by Patti Loveless (cheesy 90s country but it just does it for me) and I’m Moving On by Rascal Flats (That song was for me leaving Welch College in 2002 what Plankeye and Hootie were for me this time).

  • July 12, 2019 at 9:21 am

    Thanks for the comments, guys.

    Goodbye by Plankeye definitely deserves to be in this list but I wanted to highlight some other songs since you had already mentioned that one in your Hootie article.

  • June 27, 2023 at 1:07 pm

    Some good stuff here. Goodbye songs are emotional. “Angels in the Room,” about dying believers, is so meaningful. There are others.


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