10 Best Songs About Wanting To Leave

We have all had the urge to leave. Sometimes we find ourselves in a relationship that isn’t working or stuck in a dead-end job, and moving is a natural impulse. Luckily for those who need some support, musicians have been capturing the need to leave for decades. Here are some of the top 10 best songs about wanting to leave.

Whether you’re looking for songs about leaving a job you love, songs about moving to a new place, or just songs with leave in the title, this list will have you moving!

“Midnight Train to Georgia” – Gladys Knight

Perhaps one of the most iconic songs about leaving, “Midnight Train to Georgia,” tells the story of a man who wants to leave the big city to return to a simpler time. He desires to return to Georgia because he doesn’t feel he can make it in his new life.

“Midnight Train to Georgia” was a massive hit when released in 1973. It ranked number one on the Billboard Hot 100 and won a Grammy award in 1974. The Grammy Hall of Fame inducted it into their list in 1999.

“Leaving on a Jet Plane” – John Denver

“Leaving on a Jet Plane” is one of the best songs about leaving someone when you don’t want to. The singer needs to leave but begs his lover to wait for him. He even promises his loved one that he’ll come back from wherever he’s going with a wedding ring.

John Denver wrote and released the song in 1966, but the band Peter, Paul, and Mary also covered the song in 1969. While John Denver’s version never ranked on the charts, Peter, Paul, and Mary’s version ranked number one on the Billboard Hot 100.

“These Boots Are Made for Walkin’” – Nancy Sinatra

Nancy Sinatra sings “These Boots Are Made for Walkin’” without hesitation or regret. In Sinatra’s song, she recognizes that her lover has been philandering and that it’s time for her to leave.

Nancy Sinatra, the oldest daughter of massively successful and famous singer Frank Sinatra, released the single in 1966. Although a man was initially supposed to sing the song, Nancy Sinatra’s version turned it into a feminist anthem. It is often the soundtrack in films at transitional moments of women’s empowerment.

“I’m Like a Bird” – Nelly Furtado

“I’m Like a Bird” is a song off Nelly Furtado’s album Whoa, Nelly!, released in 2000. Furtado sings about not wanting to get too close to someone because she will undoubtedly leave. 

The song is ultimately a tragic tale about someone unable to receive intimacy and, like a bird, wants to fly away at the first sign of intimacy.

Furtado has received mixed reviews throughout her career, but this album was a smash hit. Part of that success is due to Furtado’s fusion of many different musical influences, like pop, R&B, and Latin club music.

Though not every one of her influences is present in “I’m Like a Bird,” the eclectic song remains one of the best songs about leaving.

“Just Leaving” – Dolly Parton

Dolly Parton released “Just Leaving” on her 2011 album Better Day. In “Just Leaving,” Parton sings about leaving a town, space, and relationship that no longer serves her. Though she does not know what the future will bring, getting out is the only option in front of her. 

Dolly Parton is a behemoth in the music scene. Though her style is decidedly country, she is well known for her universal song lyrics, advocacy work, and appearances in movies like Steel Magnolias and 9 to 5.

“Homeward Bound” – Simon and Garfunkel

Easily one of the 10 best songs about wanting to leave, Paul Simon wrote “Homeward Bound” after exploring England to derive inspiration from the British folk music community. He wrote the song to express his yearning for his girlfriend and how much he missed his home.

“Homeward Bound” reached number 5 on the Billboard Hot 100 chart when Simon & Garfunkel released it in 1966. It was a track on the Parsley, Sage, Rosemary, and Thyme record by the duo. People speculate that Simon wrote it at a train station in England, but this may just be a rumor.

“Leaving on Your Mind” – Patsy Cline

Patsy Cline sings “Leaving On Your Mind” from the perspective of a woman who senses that her lover has the itch to leave.

In one of the only songs about leaving someone you love on this list from this vantage point, Cline encourages her partner to hurt her feelings now rather than later. “I may learn to love again,” she promises.

“Leaving On Your Mind” was first recorded in 1962 by a singer named Joyce Smith. A few months later, Smith’s version was not succeeding on the charts, and Cline recorded another version. Cline’s version went on to rank highly in the Billboard Country Charts.

“Leave (Get Out)” – Jojo

Jojo broke through the music scene when she was 13 years old. Her song “Leave (Get Out)” reflects the tender heartbreak of first love. She sings to a boyfriend who has cheated on her and demands that he leave.

Since her teenage stardom, Jojo has struggled to find her foothold in the music industry. Many of her challenges came from being in a dysfunctional professional relationship with her label, joining the ranks of Kesha and Taylor Swift in fighting for personal and artistic control of their work and selves against profit-hungry record labels.

“Bye Bye Bye” – *NSYNC

Another early 2000s pop hit, “Bye Bye Bye” by *NSYNC chronicles a break-up from the perspective of the person leaving. The members of *NSYNC sing about packing their bags and leaving a toxic relationship.

*NSYNC was a world-famous boy band making music at the turn of the millennium. Part of their success was due to Total Request Live, a TV show on the MTV network that helped propel the careers of pop, rock, and R&B artists.

“Move On Up” – Curtis Mayfield

The final song on this list has a more upbeat message. “Move On Up” by Curtis Mayfield is about a child growing up and finding belonging in a new phase of their lives. One of the best songs about leaving home and growing up, “Move On Up” explores the kind of growth that everyone has to do once in a while.

Curtis Mayfield was an R&B and soul artist from Chicago. Blues and Gospel music from Black churches influenced a young Mayfield as he began to find his style. In 1958, Mayfield recorded as a backup singer in the Chicago-based group The Impressions. Not long after, he began to write and record his music.

In Conclusion

Music can help us feel connected to other people going through similar challenges. Songs about packing your bags and leaving might make us feel not so alone when we’re getting ready for a big transition. Whether it’s getting out of a relationship, a city, a job, or a home, these 10 best songs about wanting to leave can help us through the tough times.


Ivan Yaskey is a Philly-born EDM and synthpop enthusiast and interviewer who recently relocated to beautiful Boston, MA.

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