17 Best Songs about Leaving and Saying Goodbye

Songs about leaving are often poignant and bittersweet, capturing the complex emotions that come with saying goodbye to a person, place, or time in one’s life. Many of these songs explore themes of loss, regret, and the passage of time, while others focus on the sense of freedom and possibility that comes with leaving behind the familiar.

One of the most iconic songs about leaving is “Leaving on a Jet Plane” by John Denver. The song’s simple yet powerful lyrics capture the pain and longing that come with leaving someone behind, while its memorable melody and soaring chorus have made it a timeless classic.

Another popular song about leaving is “Don’t Think Twice, It’s All Right” by Bob Dylan. The song’s lyrics explore the aftermath of a relationship ending, with Dylan acknowledging the pain of parting ways while also asserting his independence and resilience.

Other notable songs about leaving include “Go Your Own Way” by Fleetwood Mac, “Goodbye Yellow Brick Road” by Elton John, and “So Long, Marianne” by Leonard Cohen. These songs offer a range of perspectives on leaving, from the sense of liberation that comes with striking out on one’s own to the heartache of saying goodbye to a beloved partner or friend.

Overall, songs about leaving offer a poignant and often cathartic reflection on the complexities of change and transition in our lives. Whether we are leaving behind a person, place, or phase of life, these songs remind us that saying goodbye is never easy, but it is often necessary for growth and self-discovery.

1. Leaving New York – R.E.M.

“Leaving New York” is a poignant song by American rock band R.E.M. It was released in 2004 and was the lead single from their album “Around the Sun.” The song is about leaving a place and the emotions associated with it. The lyrics are reflective and personal, with lead singer Michael Stipe singing about leaving New York and the bittersweet feelings that come with leaving behind a familiar place. The song has a mellow, atmospheric sound that fits well with the introspective nature of the lyrics. It was praised by critics for its understated beauty and has become a fan favorite. “Leaving New York” is a touching tribute to the feelings of nostalgia and loss that come with leaving a place that has been important in one’s life.

2. 50 Ways to Leave Your Lover – Paul Simon

“50 Ways to Leave Your Lover” is a song by American singer-songwriter Paul Simon, released in 1975. The song’s upbeat melody and catchy chorus belies its darker message, which outlines a series of humorous and inventive ways to end a romantic relationship. Simon’s clever wordplay and sly humor make “50 Ways to Leave Your Lover” a classic example of his songwriting prowess, while the song’s catchy beat and infectious chorus have made it a staple of radio and popular culture for decades. The song’s upbeat sound and clever lyrics have made it a favorite among fans of Simon’s work and lovers of 70s music alike.

3. American Pie – Don McLean

“American Pie” is a classic song by singer-songwriter Don McLean, released in 1971. It is a nostalgic tribute to the early days of rock and roll and its impact on American culture. The lyrics are filled with references to various artists and events in music history, including Buddy Holly, The Beatles, and the Rolling Stones. The song has a memorable melody and a sing-along chorus that has made it a staple of classic rock radio. “American Pie” has been analyzed and interpreted by music scholars and fans alike, and remains one of the most iconic songs in American music history.

4. On The Road Again – Willie Nelson

“On The Road Again” is a classic country song written and performed by legendary singer-songwriter Willie Nelson. Released in 1980, the song is a celebratory anthem for life on the road and the thrill of adventure. Its catchy melody and sing-along chorus have made it an enduring favorite of music lovers of all ages, and its iconic opening guitar riff is instantly recognizable to even the most casual listener. With its optimistic lyrics and upbeat tempo, “On The Road Again” captures the spirit of wanderlust and the joys of the open road, making it a perfect soundtrack for road trips and travel adventures.

5. Hey Thats No Way to Say Goodbye – Leonard Cohen

“Hey, That’s No Way to Say Goodbye” is a melancholic yet poetic ballad written by Leonard Cohen, the iconic Canadian singer-songwriter. The song was originally released in 1967 and has since become a classic love song, covered by many other artists. The song features Cohen’s introspective lyrics and haunting melody that captures the pain of a relationship ending. The slow, soft guitar strums, and Cohen’s tender vocals make the song an emotional experience, as he reflects on the end of a love affair with poetic grace. The song’s beauty lies in its simplicity and the universal nature of its message, as it speaks to the experience of love and loss that many people have gone through.

6. Farewell, Angelina – Bob Dylan

“Farewell, Angelina” is a song written by Bob Dylan in the early 1960s. The song tells the story of a woman named Angelina who must leave her lover and go on a journey. The lyrics are full of vivid imagery and metaphors, and the melody has a haunting, mournful quality. “Farewell, Angelina” has been covered by many artists over the years, including Joan Baez, who had a hit with her version in 1965. The song has been praised for its poetic lyrics and emotional depth, and is considered one of Dylan’s early masterpieces.

7. If You Leave Me Now – Chicago

“If You Leave Me Now” is a ballad by American rock band Chicago, released in 1976 as the lead single from their album “Chicago X”. The song is a melancholic and emotive track that features a prominent acoustic guitar melody and vocal harmonies, with lyrics about the pain and heartbreak of a failing relationship. The song became one of Chicago’s most successful and well-known songs, reaching No. 1 on the US Billboard Hot 100 chart and earning the band a Grammy Award for Best Pop Vocal Performance by a Duo, Group or Chorus. It remains a popular classic rock ballad and a staple on soft rock radio stations.

8. Goodbye My Friend – Aaron Neville and Linda Ronstadt

“Goodbye My Friend” is a song performed by Aaron Neville and Linda Ronstadt, and was released in 1991. The song is a tender tribute to a friend who has passed away, and speaks to the heartache and loss that comes with saying goodbye. The lyrics are simple yet deeply emotional, and Neville and Ronstadt’s soulful vocals are perfectly matched to the song’s poignant message. “Goodbye My Friend” has been embraced by audiences as a comforting and healing anthem, and remains a beloved classic in the canon of contemporary ballads.

9. Sugar Mountain – Neil Young

“Sugar Mountain” is a folk-rock ballad written and performed by Neil Young. The song is a nostalgic tribute to his lost youth and the bittersweet memories of growing older. The lyrics describe a magical place called Sugar Mountain where everything is possible, and time stands still. Young’s voice is plaintive and melancholic, and his finger-picking guitar adds to the wistful mood of the song. “Sugar Mountain” has become a classic in Young’s repertoire and is often played at his concerts. The song’s poetic lyrics and haunting melody make it a timeless ode to the fleeting nature of youth and the power of memory.

10. Goodbye Blue Sky – Pink Floyd

“Goodbye Blue Sky” is a song by Pink Floyd, featured on their critically acclaimed 1979 album, “The Wall”. The track is a haunting ballad that tells the story of a child’s experience during wartime, and serves as a powerful commentary on the horrors and destruction of conflict. The song features atmospheric instrumentation, including gentle acoustic guitar and ethereal vocal harmonies, which create a dreamlike soundscape. “Goodbye Blue Sky” showcases the band’s masterful ability to blend poignant storytelling with intricate musical arrangements, making it one of Pink Floyd’s most memorable and evocative tracks.

11. Ruby Tuesday – Rolling Stones

“Ruby Tuesday” is a classic rock ballad released by the Rolling Stones in 1967. It was written by Mick Jagger and Keith Richards and is named after a restaurant chain. The song has a melancholic tone and tells the story of a woman who refuses to be tied down to a traditional life, instead choosing to live freely and explore the world around her. Its haunting melody and introspective lyrics made it a favorite among fans and critics alike, cementing its place in rock history. The song has been covered by numerous artists over the years, but the original remains a timeless classic.

12. Leaving on a Jetplane – John Denver

“Leaving on a Jetplane” is a classic song written by John Denver in 1966. The song was first recorded by the Chad Mitchell Trio but became a hit when it was covered by Peter, Paul and Mary in 1969. The song features Denver’s signature acoustic guitar sound and heartfelt lyrics about saying goodbye to a loved one before leaving on a journey. The song’s memorable chorus has made it a popular choice for singalongs and covers over the years. Its universal message of parting ways with someone you love has resonated with audiences around the world, making it a timeless classic.

13. She’s Leaving Home – The Beatles

“She’s Leaving Home” is a song by the English rock band The Beatles, released on their 1967 album “Sgt. Pepper’s Lonely Hearts Club Band.” The song is notable for its narrative approach, telling the story of a young girl who runs away from home to escape a life of conformity and finds solace in the freedom of the city. The song is a poignant reflection on the generational divide of the time and the tensions between young people and their parents. The melody is gentle and wistful, underscoring the melancholic lyrics and adding to the emotional impact of the song.

14. If Leaving Me is Easy – Phil Collins

“If Leaving Me is Easy” is a melancholic ballad by English musician Phil Collins. Released in 1981, the song talks about the emotional pain of a breakup and the difficulty of letting go of someone you still love. Collins’ soulful voice and poignant lyrics blend perfectly with the gentle piano melody, creating a moving and heartfelt song that has resonated with audiences for decades. The song’s chorus, which repeats the title phrase, is particularly memorable and has become a popular sing-along anthem for those going through similar heartbreak. “If Leaving Me is Easy” is a powerful and emotionally charged ballad that showcases Collins’ exceptional musicianship and songwriting skills.

15. Goodbye Stranger – Supertramp

“Goodbye Stranger” is a 1979 hit song by the British rock band Supertramp. The song was written by Roger Hodgson and became one of the band’s most recognizable and beloved songs. The song tells the story of a man who is saying goodbye to a woman he loves but knows that he can never be with. The lyrics express the man’s sorrow and the sense of loss that comes with the end of a relationship. The song is notable for its catchy melody and upbeat tempo, which contrasts with the bittersweet lyrics. “Goodbye Stranger” remains a popular song and has been covered by several artists over the years.

16. Candle in the Wind – Elton John

“Candle in the Wind” is a moving ballad written by Elton John and Bernie Taupin in 1973. The song was originally a tribute to Marilyn Monroe, but later became an ode to Princess Diana after her death in 1997. The lyrics paint a picture of someone who was once bright and full of life, but whose light has since faded away. The song’s mournful tone and powerful melody have made it a popular choice for funerals and other solemn occasions. Elton John’s heartfelt delivery of the lyrics, combined with the soaring melody and melancholy piano, make “Candle in the Wind” a timeless tribute to those we’ve lost.

17. Hit The Road Jack – Ray Charles

“Hit the Road Jack” is a classic rhythm and blues song recorded by Ray Charles in 1961. The song features a catchy call-and-response chorus that has become an iconic part of American popular culture. The lyrics tell the story of a man confronting his lover who wants to leave him, with the man urging her to “hit the road.” The song’s upbeat melody and Charles’ signature soulful vocals make it a staple of oldies radio and a popular choice for covers by contemporary artists. “Hit the Road Jack” is a timeless anthem of empowerment, reminding listeners that they have the power to move on from toxic relationships and stand up for themselves.