Sometimes, there’s nothing harder than a goodbye. We know that goodbyes signal the end of something, and when we’re not ready to let go of it, they can tear us apart. They’re an inevitable part of life for sure, but that never makes them any easier. Whether it’s a goodbye that ends with a “see you soon” or one that comes with uncertainty, it’s easy to tear up whenever these situations arise.
Like most of life’s harsher moments though, we have the gift of music to help us through them. Some people prefer happier songs when they’re down, but I personally love sad songs to reflect my mood and sulk in my feelings. Luckily, for weirdos like me, there are a plethora of songs about goodbyes.
Goodbye songs often vary in their approaches, but the core is usually the same: for better or for worse, this part of life is over and it’s time to let it go. Some are sadder than others, while some are simply bittersweet. Overall, though, these are ten of the best goodbye songs to help you the next time life throws one at you.
10. "Hello, Goodbye"- The Beatles
Despite the sad nature of goodbyes, we’re starting this list with a fun song courtesy of Sir Paul McCartney. The product of a lyrical exercise of oppositions, “Hello, Goodbye” became one of many number one hits for The Beatles. It also proved to be quite divisive among critics and fans, with John Lennon having a particular distaste for it as well.
Either way, McCartney’s tune is an iconic goodbye song with plenty of pop charm. It takes a lyrically simple approach to show how topsy-turvy the singer’s relationship is. The crown jewel of this dysfunctional couple though is that she’s always saying goodbye when he says hello.
As a goodbye song, “Hello, Goodbye” uses that constant refutation to show how frustrated the singer has become. No matter how much he loves her or what he does, he’s always met with a goodbye. Like many of us, he doesn’t want to hear the dreaded word, but it’s all he’s getting from this relationship. While it’s a toxic situation for the singer, he can’t let her go, which is why he keeps sending all those hellos.
Despite McCartney’s playful approach, “Hello, Goodbye” illuminates our reluctancy to accept goodbyes. Even though this relationship has brought the singer nothing, he still can’t accept that whatever they had is now over. Although they are a complete mismatch, the speaker’s love will likely keep him there no matter how many times he hears the word goodbye.
9. "Letter to Hermione"- David Bowie
There’s perhaps no goodbye song more common than the classic breakup song. Unlike our previous entry, the breakup song typically reeks of emotional devastation, lamenting the existence of a goodbye. Enter David Bowie, who sullenly bid farewell to his first love, Hermione Farthingale, in his song “Letter to Hermione.”
With tender vocals, Bowie enchantingly writes to his lover, who has moved away. He’s heartbroken, not just because she left him but because she’s becoming someone else. Hermione now “sparkles like a different girl” and even sees other guys now. Devastated, the singer doesn’t know what to do besides write this somber letter of desperation.
On one level, Bowie’s song shows the delusions we hold on to during goodbyes. In the letter, the singer wonders if Hermione ever cries for him. While we have no idea if she does, it seems more like he’s projecting his own sadness onto her in hopes that there’s still something to clutch on to.
Most of all though, “Letter to Hermione” shows the confusing emotions a goodbye can cause. The singer often repeats that he’s not sure what to do, as the situation has gotten away from him. The quick influx of change has completely overwhelmed him, leaving him helpless. Sadly, that’s just how goodbyes can feel sometimes, a sentiment that Bowie’s song captures with fervent melancholy.
8. "Ruby Tuesday"- The Rolling Stones
Another goodbye song of the 60’s, “Ruby Tuesday” proved to be a massive success for The Rolling Stones. It would eventually become their fourth number one hit, as well as one of their most beloved songs.
Amidst all that success though lies a tender goodbye, one based on the band’s real experience. Keith Richards reportedly wrote the lyrics about his then girlfriend Linda Keith, a popular model during the 60’s. She was also notorious for her interest in the rock music scene and clearly had an impact on Richards himself.
As such, “Ruby Tuesday” captures the free spirit of Keith and the 60’s itself, documenting an enchanting woman who just can’t be pinned down. The singer is clearly encapsulated by Ruby's independence, even noting that a name is too limiting for her. However, he also knows that her freedom means she can’t stay, leading to an unfortunate goodbye.
Sadly, the goodbye at the heart of this song is simply inevitable. Ruby must leave because that’s the only way she can maintain her independence. Yet, it’s that free spirit that the singer loves most about her. Ruby will always leave, and the singer will love her for it, but still loathe the goodbye.
In a mature twist, the singer has seemingly accepted this fate and bids her goodbye. Still, he admits he will miss her and the unique approach she brings to life. “Ruby Tuesday” is a goodbye that must take place, even if that acceptance can never erase the sadness.
7. "Have Yourself A Merry Little Christmas"- Judy Garland
Perhaps the most covered song on this list, most people probably don’t associate “Have Yourself A Merry Little Christmas” with tearful goodbyes. That’s more than likely because the most popular version is Frank Sinatra’s, which feels more tender than depressing.
However, the original version, which was written by Hugh Martin and Ralph Blane for the Christmas film Meet Me in St. Louis, offers a pretty emotional farewell for the most wonderful time of the year.
In the film, Judy Garland’s character, Esther, sings this song to her sister as everything changes for their family. They are moving away from St. Louis, a place that has been a safe home for years. To ease her, Esther breaks into the solemn song, urging her to enjoy this Christmas while everyone is still here.
It's a tender scene, but the song itself fully highlights the highs and lows of a goodbye. Garland’s vocals are reassuringly beautiful, but the heartache of saying goodbye still bleeds through. The singer also acknowledges the encroaching change, which terrifies her. She doesn’t admit defeat, however, promising that “someday soon, we all will be together.” While she has no way of ensuring this, she must remain hopeful because that’s all she can do.
Although there’s a somberness in this goodbye, there’s also a strong sense of hope. With no power to control the future, all we can do is enjoy the moment and hope for the best. What will happen will happen, but as for now, all we can do is live the present and have a merry Christmas.
6. "The Call"- Regina Spektor
Another movie song, Regina Spektor’s “The Call” is admittedly far less listened to than our last entry. However, this overlooked track, which was written for The Chronicles of Narnia: Prince Caspian, provides an emotional goodbye in a unique way.
A bittersweet song, “The Call” plays when the Pevensie children must leave Narnia at the film's end. With all the adventures they’ve been through, Narnia has become an integral part of their lives, but it’s time to say goodbye.
Surprisingly, Spektor’s song doesn’t explore Narnia directly. Instead, it examines the difficulty of a goodbye through a story about a lover leaving for war.
As the goodbye happens, the singer offers up advice for surviving these changes. She emphasizes the importance of maintaining friendships, as well as the memories of those no longer with us. Most of all though, the singer refuses to say goodbye, believing that there’s no need since her lover will return.
For a goodbye song, Spektor skirts around actually saying goodbye. The singer outright refuses to accept this goodbye because the thought of her lover not returning is too much to bear. With a realistic chance that he never returns, it's just easier to believe otherwise.
But where there's denial, there's also opportunity to be willfully hopeful. "The Call" accepts goodbyes as difficult entities, but not insurmountable ones. With memories that can never be killed and friends worth dying for, even war itself is not the end. Spektor leaves the song’s ending ambiguous, but with a series of hopeful barbs, we know the singer will be okay.
5. "Maggie May"- Rod Stewart
Perhaps the gold standard for breakup songs, few songs land with the emotional intensity that Rod Stewart’s “Maggie May” does. Based on Stewart’s own experiences with an older woman, “Maggie May” is now his most iconic song, as well as a tragic goodbye to a tragic romance.
After a classical guitar intro, Stewart’s raspy vocals tell the story of a young lover telling his girlfriend goodbye. The singer wakes her up, letting her know that he needs to move on with his life. He then admits how much she has meant to him, before explaining that she has done nothing but mess around with his life. Finally, saying everything he’s been keeping inside, the singer finishes by wishing that he’d never seen her face.
Of all the goodbyes on this list, this is probably the most deserved. The singer has given every part of himself to Maggie, who has never reciprocated his love. Unlike the fun tryst in “Hello, Goodbye” though, this is a fully blossomed romance that has kept him from continuing his life. Luckily, the singer has finally realized what Maggie has done and must say goodbye.
It’s a goodbye that’s completely deserved, but harsh, nonetheless. Even though this needs to be over, the singer finds difficulty in admitting how much he’s really lost. Still, he must move on and we’re grateful when he finally does. Sometimes we’re forced to say goodbye, but that doesn’t mean it isn’t the best thing we can say.
4. "Wednesday Morning, 3 A.M. (Live at the Lincoln Center, New York)"- Simon and Garfunkel
A subversive goodbye, “Wednesday Morning, 3 A.M.” is a typical ballad from the brilliancy of Simon and Garfunkel. Like many of their songs though, it must be listened to live so that the full sadness of the goodbye can be experienced.
With their typical finger picking and phenomenal vocal harmony, Simon and Garfunkel take us into the world of someone ready to leave their lover at 3 A.M. The singer begins by describing his sleeping lover, whose beauty lays covered in the moonlight. But this is juxtaposed by the singer’s anxiety, which urges him to leave her before she wakes up. The third verse finally tells us why though, as the singer robbed a liquor store earlier. Finally, he lingers over her for a moment then leaves before the morning sets in.
Lyrically, Simon’s storytelling is unmatched. He builds up this idyllic life with a gorgeous lover before revealing that the singer gave it up for “thirty-five dollars and pieces of silver.” He then lets him soak up the guilt, before forcing him to leave.
It’s a goodbye of true dramatic tragedy, as the speaker has no one else to blame but himself. Simon even specifically alludes to the theater as the Greek tragedies often featured heroes who’d create their own downfalls.
While we sympathize with the singer and the intensifying guilt he feels, we also feel anger that he’d ever let this happen. Some goodbyes are unavoidable, but this one wasn’t, perhaps making it harsher than most.
3. "Don't Speak"- No Doubt
One of the most heart wrenching ballads of the 90’s, not too much else can be said about No Doubt’s pop masterpiece, “Don’t Speak.” Of course, as a major Gwen Stefani fan, it would always rank highly here. But it’s the brutally succinct approach that Stefani takes here that makes this goodbye so personable.
Written by Stefani after fellow bandmate Tony Kanal ended their seven-year relationship, “Don’t Speak” revels in the heartache of an active breakup. The singer recognizes that her relationship is dissolving before her and confronts her lover. She laments how close they once were, even being best friends, before pleading for him to not speak another word.
With Stefani’s yearning vocals, the singer’s desperation really shines through. She recognizes everything that’s happening, as well as what she’s about to lose. But she can’t do anything about it, so she opts to not hear the goodbye instead.
It’s a brutal goodbye to listen to mostly because of how relatable the situation is. Anyone who has been broken up with recognizes when your lover starts to pull away. That gut-wrenching feeling when you know that it’s over is disabling, but unmistakable. Worse of all, it really does feel like you lose your best friend, as Stefani sadly notes.
The lyrics are never complex, but their accessibility makes this sad goodbye all inclusive. Afterall, the simple phrase “don’t speak” reflects our desire to skip the sad goodbye all together. However, that won’t stop the pain, as the singer finds out herself in this grueling goodbye.
2. "Boots of Spanish Leather"- Bob Dylan
In second place comes this seemingly straightforward folk ballad from the freewheeling Bob Dylan. Comprised of just his signature sandpaper vocals and fingerpicked guitar though, “Boots of Spanish Leather” forgoes any fancy musical composition for a masterfully told story unlike any other on this list.
Told from alternating perspectives, Dylan’s song explores the story of two lovers saying goodbye as one departs for Europe. Before one lover leaves, she asks if she can bring him back a gift. He rejects her offer though, saying that all he wants is for her to return. They go back and forth for a while, with his lover pleading that she send him something nice to ease his time without her. However, he never concedes, insisting that he’d forgo all of the world’s riches just for her kiss.
Eventually though, he receives a letter from his lover saying that she doesn’t know when she’ll come back, if she does at all. He concludes that she’s no longer his and has moved on. Before finally saying goodbye though, the singer asks for a gift: Spanish boots of leather.
It’s a drawn-out goodbye, one that slowly creeps before it’s finally felt. His love and adoration for her, although romantic, ultimately blinds him to the fact that he’s losing her. Perhaps she never even intended to return, which would explain why she insists on sending gifts to ease her guilt. Either way, he wouldn’t notice.
The goodbye aspect is heart wrenching, showcasing how our own passions can doom us. However, the ironic ending leaves him with more than he originally had. Even though his emotions blinded him for a long time, he snaps out of it at last to get something of value. Moving on is hard, but the lover has already taken steps forward, in expensive boots, nonetheless.
1. "Good Riddance (Time of Your Life)"- Green Day
But despite Dylan’s poetic goodbye, there’s only one song that truly embodies the bittersweet and inevitable nature of a goodbye. Unsurprisingly, this comes in the form of the breakup hit by rock band Green Day, “Good Riddance (The Time of Your Life).”
Like many other songs on this list, it was based on true events. Lead singer Billie Joe Armstrong reportedly wrote it after his girlfriend moved to Ecuador. Feeling both the anger and sadness of losing his love, Armstrong wrote this ballad which has since become one of the band’s biggest hits.
Although the title reflects Armstrong’s bitter feelings, the rest of the song sincerely shows why this goodbye is so difficult. After a quiet f bomb, the singer describes the current situation they’re in. He mentions how time has dragged them here, a point where their paths diverge. Instead of reeling in the sadness though, he ushers her on, hoping that she’s had as much fun as him.
In the next verse, he focuses on the memories they’ve made along the way, urging her to always cherish them. He also admits that they were worth every second, despite the pain of this goodbye. Finally, he gives her the same wish as earlier: “I hope you’ve had the time of your life.”
Everything about Armstrong’s song reflects the complexity of a touching goodbye. The singer is bitter, but not enough that he’d forsake this departing moment. Through the pain, he loves her once more by biting his tongue and wishing her the best in life.
Most of all though, he wouldn’t trade this experience for anything. He knows how important his memories are, as well as the experience of knowing her. The goodbye hits him out of nowhere, but that’s just the unpredictability of life. Time will likely throw more goodbyes his way, as that’s just how life works.
What Armstrong’s song reminds us though is that life isn’t about goodbyes. We don’t live to say goodbye. Rather, we say goodbye because of the beautiful moments we’ve shared together.
Sometimes we must say goodbye, but it’s not all bitter sadness. We should embrace the idea that life ever gave us someone worth crying about when they're gone. Maybe we’ll see them again, maybe we won’t. There’s always hope, but as long as you hold those memories close to your heart, no goodbye is ever final.
