What Songs Are on Your Fall Playlist?

It’s fall, and I’m so excited. The leaves are changing colors and falling off the trees, which means that it is finally time to pull out my favorite fall playlist on Spotify. What’s on your fall playlist?

Here are some of my favorite songs that I can’t wait to play this season:

1. Girls Just Want to Have Fun – Cyndi Lauper

This song is a classic, originally recorded by Cyndi Lauper in 1983. It’s about women who are independent and don’t need a man to have fun.

The lyrics are quite empowering for those of us who like to think we’re independent and free-spirited:

Say what you will about the guy in the song—who cares? He’s no Fun Boy Ricky!

2. I Will Wait – Mumford & Sons

To start with, the song is about a man who is waiting for his love to return.

The way that Mumford & Sons has set up the piece makes it sound like he’s been waiting for a long time, and that now he’s just done with it all.

There’s a strong melody in this track—the chorus (“I will wait… I’ll wait… I’ll wait…”) repeats as if to say “I know you’re coming back soon.”

In addition to being catchy, this line also has a strong rhythm; each word in the phrase falls on one beat of the measure except for “you” which lands on two beats after an anticipatory pause before “coming back.”

The song seems like it would be easy enough to dance along with but perhaps not quite as fun as other songs on this list; maybe because of its heaviness or perhaps due to its theme of yearning and waiting.

3. The Boys of Fall – Kenny Chesney

One of the more popular songs on my fall playlist is “The Boys of Fall” by Kenny Chesney.

The song is about a guy who misses his high school sweetheart and reminisces about their time together. It was released in 2006, which means it’s been around for almost ten years now!

This makes me feel old, but also very nostalgic for high school days—and the football team! Yes, this song is about both football and those boys who were on it.

I love how this country tune describes a certain coach and how he taught these boys to play hard: “But there was one man who taught us things/That we’ll never forget… He said if you’re gonna play for me then you gotta do your best.”

I don’t know why I like this line so much; maybe because it reminds me that if you don’t give everything you’ve got then what are you even doing? What’s the point?

4. Hurricane Season – Trombone Shorty

This song was written by Trombone Shorty, who took inspiration from his father’s experiences during Hurricane Katrina.

The song is about going through the aftermath of this disaster and trying to rebuild your life.

It also talks about how many people lost everything they had because of the storm, including their homes and possessions.

The music video features footage from New Orleans before and after Hurricane Katrina hit in 2005.

5. Back to Tennessee – Billy Ray Cyrus

You can’t go wrong with Billy Ray Cyrus. When it comes to country music, he’s a legend.

He had hits in the ’90s like “Achy Breaky Heart” and “Somebody New.”

His daughter Miley Cyrus is also a star, but her dad has been rocking the stage since before she was born!

He’s had songs recorded by Elvis Presley, Kenny Rogers, Roy Orbison, and many others. He even sang backup for Waylon Jennings!

His latest album features some of his greatest hits including “Back to Tennessee” which we’re listening to right now!

6. Falling Slowly – Glen Hansard and Marketa Irglova

“Falling Slowly” is a song by Glen Hansard and Marketa Irglova from the 2006 Irish film “Once”.

The song was written by Glen Hansard, who also sang it as his character in the movie.

It was released as a single on May 22, 2007, and reached number 24 on Billboard Hot 100. In 2008, it earned Glen Hansard an Academy Award nomination for Best Original Song; he lost to “You Haven’t Seen The Last of Me” by Cher.

7. If I had a Boat – Lyle Lovett

Lyle Lovett is a unique artist. His style and sound is not like anything else out there, which makes for a great listen.

He has an amazing voice that sounds like no other, and he plays an impressive guitar as well.

Lyle Lovett has also been known to write some catchy tunes!

You won’t see many artists with his unique style or talent, so take some time this fall to enjoy one of the best songwriters on the scene today.

8. Make Up Your Mind – The Band Perry

Make Up Your Mind, originally released in 2010 by The Band Perry, is a song about indecision.

The lyrics are rich with imagery and can be interpreted as either referring to two different people or one person with multiple sides to their personality.

“You want me here / I want you there…” the singer sings, illustrating that she wants both options: to stay with her lover and go with him on his adventure.

On one hand, it’s exciting to travel and explore; on the other hand, it would mean leaving your lover behind—and who wants that?

We’ve all been there at some point in our lives: wanting two things at once but unable to choose between them because of this inner conflict.

The song makes us feel like we’re experiencing that moment firsthand as we watch our character wrestle with her options, trying desperately not just for herself but also for someone else who may feel just as torn about what he wants from life.”

9. Ring of Fire – Johnny Cash

“Ring of Fire” is about a love triangle between Johnny Cash, June Carter Cash, and her husband.

June Carter Cash was married to Bob Wootton before she met Johnny Cash.

The two had different tastes in music: he liked country and western while she preferred jazz. When they got together, they decided to play their favorite songs together on guitar and piano.

One day while they were doing this, they came up with the idea for “Ring of Fire.”

10. White Flag – Dido

White Flag is the eighth track on Life for Rent, Dido Armstrong’s second studio album. Written by Dido and Rollo Armstrong, White Flag was released as a single in 2003 and has since become one of Dido’s most successful singles to date.

The song reached #1 on the Billboard Hot 100 chart and earned her two Grammy nominations for Record of the Year and Best Female Pop Vocal Performance; it also won a BRIT Award for Best British Female Solo Artist.

Simply put: if you’re looking for some chill tunes to listen to this fall season, White Flag should be your go-to song!

11. What Hurts the Most- Rascal Flatts

A song that’s been on my playlist for years, “What Hurts the Most” is a tale of a woman who is in love with a man who is married.

She knows he loves her; they have an undeniable connection and even though he knows she’s hurting, he doesn’t leave his wife or the woman that he loves.

It was released in 2004 and won Grammy Awards for Best Country Song and Best Country Song Vocal Performance by a Duo or Group (the latter being shared with Rascal Flatts).


So, we’ve covered a lot of ground here. We’ve talked about some of the most popular songs on fall playlists and why they are so popular.

You may have even found yourself adding some of these tracks to your own playlist!


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