30 Best Songs About Leaving (Work, Home or the Past Behind)

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Written By Will Fenton

Founder of MidderMusic. From numerous bands to stints working in music shops, read more about me on the 'Here's My Story' page!

Have you packed your bags yet?

Wait, do you even have the right words to tell your loved ones before you leave? 

Let’s face it. 

Goodbyes are painful. 

It doesn’t matter if you are going away for a day, a month, or forever. 

Finding the right words to express yourself at this moment can be challenging. 

But sometimes, goodbyes are a chance to make a fresh start.  

And even if it hurts, you know this is your best opportunity to make all the wrongs right and begin on a clean slate. 

No matter what you are going through, there’s always a song to relieve your emotions. 

And below are the 30 best songs about leaving to make your goodbyes less painful. 

Let’s start with a Willie Nelson classic.

1. “On The Road Again” by Willie Nelson

Many artists spend their time on the road. 

And it’s little surprise most of them compile moving lyrics about their lonely trips away from their loved ones. 

Willie Nelson captures such emotions in his 1979 country rock. 

2. “If You Leave Me Now” by Chicago 

One of Chicago’s best-ever hits is about a man begging his lover to stay. 

“If you leave me now, you’ll take away the biggest part of me/ No, baby, please don’t go.”

The lyrics accentuate the feeling that you won’t even realize the song doesn’t have a chorus. 

And by the way, Chicago’s song topped the US Billboard 100 chart for two weeks.

It also won a Grammy award in the Best Performance by a Duo and the Best Arrangement Accompanying Vocalist categories. 

3. “Goodbye, Goodbye” by Tegan And Sara

The indie pop girl duo released their farewell song in 2013. 

Despite the upbeat melody, the song has rather sad lyrics about a broken relationship. 

This is the perfect tune when you want to shut down an ex-lover who took you for granted. 

4. “Candle In The Wind” by Elton John 

Elton John’s song was the perfect tribute to actress Marilyn Monroe, who sadly succumbed to a drug overdose in 1962.

By comparing Monroe’s life to a candle in the wind, Elton illustrates the sex goddess’ vulnerability. 

The moving ballad became one of Elton John’s greatest-ever songs. 

5. “Goodbye Stranger” by Supertramp 

The subject matter of Supertramp’s song is goodbye. 

And he struggles to come to terms with leaving. 

6. “Good Riddance (Time Of Your Life)” by Green Day

Not all goodbyes are painful. 

And sometimes, it’s all you need to see life from a new perspective. 

Good riddance is exactly what you would tell a toxic lover who’s decided to free you from the cage by ending the relationship. 

For Green Day, it isn’t necessarily about a broken relationship but the mentality you need to keep going.

The song has found its way into many graduation ceremonies and other occasions where goodbye is a surety. 

7. “Tears In Heaven” by Eric Clapton 

“Tears In Heaven” is a heartbreaking song about leaving that describes Eric Clapton’s huge loss.

The singer mourns his beloved Conor, who sadly passed on at four years old. 

As such, the song expresses the sad feelings we never want to talk about.

The emotional lyrics and the painful narration are impossible to ignore. 

But we hope you will have the strength to listen to the song to the last line. 

8. “Goodbye My Lover” by James Blunt 

James Blunt wrote this song for an ex-lover long after their relationship ended. 

He laments the loss of a darling and is sad that someone he loves can no longer be part of his life. 

Appearing at a UK interview, James recalls that the song is “a realization that you’ll never be with someone, but the frustration that they are still alive and out there in the world.” 

We got you, James.

Losing a loved one hurts, but goodbyes are even more painful.

9. “Goodbye My Friend” by Linda Ronstadt

Linda Ronstadt’s song describes losing a friend.

The most painful part of the narration is knowing you will never see them again. 

And the painful lyrics match the somber account.  

10. “Leaving On A Jet Plane” by John Denver 

Only goodbyes will be missing after you’ve packed your bags and are ready to go. 

A few people can relate to the agony of always staying away from the ones you love.

And John Denver’s song is yet another anthem about leaving your loved ones behind. 

It hurts to be away from them.

But you have no choice when you have a job obligation to honor.

John Denver can only say his goodbyes and hope for the best. 

11. “Careless Whisper” by George Michael

Like most sad songs about leaving, George Michael’s “Careless Whisper” is about lost love.

The singer bemoans his failed relationship after cheating on his partner. 

As a stream of negative thoughts run through his mind, a feeling of guilt and regret sets in. 

And George shares his frustrations in this song. 

12. “These Boots Are Made For Walkin’” by Nancy Sinatra 

Nancy Sinatra has had enough. 

For some time, she’s been doing her best to cope with her lover’s behavior. 

But at this point, there’s no way back for her. 

The song reached #1 on the US Billboard Hot 100 and the UK Singles charts. 

Just like Nancy Sinatra, your boots are made for walking.

And if you are going to walk away from a toxic relationship, you better start listening to the song’s lyrics now. 

13. “Un-Break My Heart” by Toni Braxton 

Unfortunately, most farewell songs are about breakups. 

And this song finds the narrator pleading with someone she loves to come back to her. 

She fast realizes that she can’t live without him, no matter how hard she tries. 

And the only way to feel complete again is to be with him. 

“Don’t leave me in all this pain/Don’t leave me out in the rain/Come back and bring back my smile.”

Only if the addressee could heal her pain.

14. “One Last Time” by Ariana Grande

Poor Ariana Grande only wants one last chance with her lover. 

She’s apologizing and saying her goodbyes at the same time. 

Regrettably, she’s in the wrong, and it’s hard to see a way back for her in the relationship. 

Maybe it’s time to move on, Ari. 

15. “Leaving New York” by R.E.M.

“Leaving New York” is the perfect tribute to the American city. 

Lead singer Michael Stipe recalls that they wrote this song on a plane while admiring the city’s beauty. 

Stipe has never hidden her admiration for New York City, calling it his second home. 

And the powerful ballad was him professing good things for the city following the September 11, 2001 attack. 

It’s hard to think of a better tribute to the beautiful city. 

16. “How Can I Help You Say Goodbye” by Patty Loveless

Patty Loveless’ emotional song has been featured in funerals, graduations, and other celebrations. 

And it follows the story of a young woman who experiences three huge losses in her life. 

The tragic things happening to her will make you feel her pain.

She’s separated from her best friend, her husband divorces her, and her mother passes on. 

Can it get any worse than that?

17. “She’s Leaving Home” by The Beatles

The Beatles’ baroque pop song tells the tale of a lonely girl who escapes from home in search of love. 

She writes a goodbye note to her parents before slipping out of the home early morning. 

The distraught parents can’t hide their pain when they learn of the girl’s disappearance. 

Interpret it how you will. 

But one message stands out in the song; money can’t buy happiness. 

18. “Hit The Road Jack” by Ray Charles 

“Hit The Road Jack” is a classic 60s song about leaving. 

While no couple wants to build their union around frequent arguments, sometimes it is inevitable. 

Like in the case of Ray Charles in this song. 

Ultimately, the woman kicks him out of the house.

Lonely and dejected, the man returns, pleading with the woman to let him back into her life. 

19. “50 Ways to Leave Your Lover” by Paul Simon 

Is there a comprehensive guide to leaving your lover?

Looks like Paul Simon might have just created one.  

“You just slip out the back, Jack/Make a new plan, Stan/You don’t need to be coy, Roy/Just get yourself free/Hop on the bus, Gus”.

It’s obvious he’s getting these tips from his mistress. 

Unfortunately, the singer only gave five tips when we expected 50. 

A sequel would have been better, Paul. 

20. “I’ll Always Remember You” by Hannah Montana

Hannah Montana assures that she will never forget the addressee, no matter their different paths in life. 

Sometimes, that’s the best you can do when the relationship hits a roadblock.  

You will find Hannah Montana’s song in graduation parties, breakups, and any other event where one chapter closes for a new one to begin. 

21. “Farewell” by Rihanna 

Rihanna’s farewell song from her Talk Talk Talk album is about saying goodbye to a lover. 

It is one of the best goodbye songs when family and friends are involved. 

22. “If Leaving Me Is Easy” by Phil Collins

Phil Collins wrote this song to express his marital problems with Andrea Bertorelli. 

The coupled had been together for five years before divorcing in 1980 on the grounds of infidelity.

And Collins expresses his anger and pain after realizing she cheated on him with a painter. 

23. “I’m Moving On” by Elvis Presley 

Elvis Presley’s song is about moving on.

Sometimes, that involves dedicating painful lyrics to a loved one.  

24. “Too Good At Goodbyes” by Sam Smith

Sam Smith wrote a breakup song inspired by his romantic affairs.

But getting dumped three times by the same person meant Sam was used to getting played at love. 

And he sees no point crying about it. 

He will say his goodbyes and move on as fast as possible. 

Taking a break from love may mend his broken heart. 

25. “Take Me Home” by Jess Glynne

“Take Me Home” is an emotional 2015 song with a twisted meaning. 

It is not about the one who broke the singer’s heart. 

But rather, that one person who saved her from sinking into her sorrow.

Heartbreaks are painful.

And it helps to have a shoulder to lean on when you need it the most. 

26. “I Will Remember You” by Sarah McLauchlan

“I Will Remember You” is another farewell song about relishing memories. 

While moving on is difficult, you can always look back at the wonderful times with a big smile. 

27. “One More Day” by Diamond Rio

One more day is everybody’s wish after a painful breakup. 

You wish to get one last chance with your loved one before they are gone. 

But many a time, it’s always too little too late. 

The song continues to grace many funeral ceremonies and breakups where one party feels they underappreciated their loved ones when they had the chance. 

28. “Never Say Goodbye” by Bon Jovi

Bon Jovi’s “Never Say Goodbye” is a beautiful song about memories

The narrator reminds everyone of the importance of keeping ties with old friends. 

If you treasure your friends and want to keep them forever, here’s the perfect tune. 

29. “Bye Bye Bye” by NSYNC

You may want to say your goodbyes with a little dance.

NSYNC’s upbeat dance pop is another popular farewell song. 

The guy in the song has had it all. 

And he’s ready to walk away from the relationship. 

30. “Hey That’s No Way To Say Goodbye” by Leonard Cohen

The last song on our list is from one of the best storytellers in musical history. 

At only 33, Leonard Cohen released a song that would cement his legendary status in the rock music scene. 

And the track finds him lamenting a lost love. 

He’s frankly disappointed at a relationship that failed to work. 

And he spends about 3 minutes calling out her ex-lover in the clearest show of frustration. 

Hey, that’s our perfect way to say goodbye. 

Songs About Leaving – Final Thoughts 

Goodbyes will make you shed a tear when you don’t want to. 

And it doesn’t matter whether you are leaving your loved one, a job, or a child. 

The repercussions must be felt for the better part of your life. 

Fortunately, listening to a beautiful playlist with calming songs about moving away can sometimes lessen the pain. 

So, the next time you are compiling your ultimate leaving playlist, we recommend the top 30 songs above. 

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