17 Best Songs about Leaving and Saying Goodbye

woman with suitcase

There’s something sad about leaving, but also something strangely liberating.

Leaving a job, a relationship, a family. It’s serious stuff that has repercussions throughout your life. Here’s our pick of the best songs about leaving and saying goodbye. There are some great songs in this playlist: some are sad, others are inspiring, but all are worthy of a listen. Enjoy.

Leaving New York – REM

This song was written with a specific meaning in mind, but you can find your own meaning in it because the lyrics are open-ended enough. Lead singer Michael Stipe said that this song is a love song to New York and how much the city had changed and healed since 9/11. However, you may see it as a song about leaving someone or something behind despite wanting to stay.


50 Ways to Leave Your Lover – Paul Simon

The man in this song seems to be cheating on his partner, and the new woman he’s with is giving him advice on how to break up. The title suggests there are fifty ways, but the song only mentions five. Paul Simon said the song is essentially nonsense, but that didn’t stop it from reaching number 1 in the US and 23 in the UK.

Related: see features on our list of songs with numbers in the title.


American Pie – Don McLean

‘American Pie’ is pretty much a memorial to the plane crash on February 3, 1959, that took the lives of Buddy Holly, The Big Bopper, and Ritchie Valens. It’s also an appreciation of the USA and all its musicians. The song came out in 1971, and the US had just landed on the moon two years prior, so patriotism was still at an all-time high. Surely you aren’t surprised that this song was number 1 in the US!

Related: see best songs for a road trip.


On The Road Again – Willie Nelson

Will Nelson wrote this song for the 1980 film Honeysuckle Rose. He was on a plane with director Jerry Schatzberg when he scribbled the lyrics on a bag. Jerry wanted a song about traveling, and Willie came up with the lyrics before he had a melody. The song became pretty popular and is a road trip favorite for many.


Hey Thats No Way to Say Goodbye – Leonard Cohen

Ending a relationship when you don’t want to is tough, but according to Leonard Cohen, teary eyes are “no way to say goodbye.” He tells his partner that their love will stay with him forever, even though they must part ways. He says, “it’s just the way it changes, like the shoreline and the sea,” as if to say that some relationships have to change and can’t be stopped, just like nature can’t be stopped.


Farewell, Angelina – Bob Dylan

Farewell, Angelina’ is like poetry that follows a pattern. The third to last line of each verse says “farewell, Angelina,” followed by describing the sky and saying he needs to leave. This song was first released in 1965 on Joan Baez’s album. Many thought that maybe Bob Dylan’s version was lost, or he never even recorded the song himself until his version came out in 1991.


If You Leave Me Now – Chicago

In this song, a man tries to convince his lover not to leave him, saying that they’ve worked too hard to leave their relationship behind. He says, “a love like ours is love that’s hard to find,” showing that he appreciates their relationship and believes he may never have something like this again. This song made it to number one in the US and UK.


Goodbye My Friend – Aaron Neville and Linda Ronstadt

This sad song is about telling a loved one goodbye. It could apply to a lover or a friend since it talks about love but uses “my friend” to address the person the singer is leaving behind. Whoever the song is about, it’s a sad departure that won’t soon be forgotten.


Sugar Mountain – Neil Young

‘Sugar Mountain’ is a symbolic place that represents childhood. “You can’t be twenty on Sugar Mountain,” so you can assume that you have to leave this place once you turn eighteen. Each verse remembers different parts of childhood, from going to the fair with your parents as a kid to sneaking a cigarette as a teen. Eventually, you feel ready to leave this place, although it feels too soon.

Related: see songs about growing up.


Goodbye Blue Sky – Pink Floyd

This song reminisces about childhood and how you realize that life isn’t as wonderful as adults make it seem once you’re an adult yourself. The singer questions why you “run for shelter” when you’re promised “a brave new world…beneath a clear blue sky.” This song is a beautiful way of saying that life isn’t what it’s all cracked up to be!

Related: see songs about childhood.


Ruby Tuesday – Rolling Stones

‘Ruby Tuesday’ was a big hit for the Rolling Stones, coming in at number 1 in the US and number 3 in the UK. It’s about losing a free-spirited lover who doesn’t want to be tied down by a relationship. “Who could hang a name on you” could be referring to marriage since it’s a common practice for women to change their last name.


Leaving on a Jetplane – John Denver

John Denver wrote this song while in an airport on a layover. He didn’t have anyone to write this song about at the time, which was the inspiration for it—he imagined having a lover that would be difficult to leave behind. (The emotion in the song is real enough that you’d never guess that!) The song was a hit, coming in at number 1 and 2 in the US and UK, respectively.

Related: see songs about flying.


She’s Leaving Home – The Beatles

She’s Leaving Home’ was inspired by a news story of 17-year-old Melanie Coe who ran away from home in 1967. The parents couldn’t understand why she’d leave because they gave her everything. The Beatles hypothesize that “fun is the one thing that money can’t buy,” which could be the reason that kids and teens choose to run away.


If Leaving Me is Easy – Phil Collins

It’s hard to get past a breakup as Phil Collins shows in this song. It seems like some time has past since he was left alone, but he still hasn’t been able to move on…probably because he still has the letters and pictures! He reveals toward the end of the song that he knew the breakup would happen because people were talking about it, and he knows that they won’t be coming back to his life any time soon.


Goodbye Stranger – Supertramp

This song is all about the freedom of spending just one night with one person and moving on the next morning. The singer says, “sweet devotion, it’s not for me,” saying that they don’t want to make a commitment to just one person so they can keep moving forward and having fun. This song made it to the Top 20 in the US but charted much lower in the UK.


Candle in the Wind – Elton John

This song doubles as a tribute to Marilyn Monroe and a criticism of how celebrities, women in particular, are sexualized in all aspects, even once they pass away. Elton John compared Marilyn to a “candle in the wind” because her life was short but busy. Norma Jeane was the name she was given at birth, so Elton used it in the song to show respect and that she was more than just the movie star Marilyn Monroe.


Hit The Road Jack – Ray Charles

This song is about a man who isn’t treated right by his partner, so he packs his bags and leaves. It doesn’t seem to be working out for his partner, either, since he calls her “old woman.” The song is catchy and short, which may be why it made it to the Top 10 in both the UK and US.