Falling into the season: 20 best autumn songs

In 1978, soul group Earth, Wind & Fire released its iconic single “September.” While the month is the start of the autumn season, EWF uses the song to reflect on a nostalgic time in their lives. As they sing on the first verse, “Do you remember / The 21st night of September? / Love was changing the minds of pretenders / While chasin’ the clouds away.” 

“Autumn Leaves” is a popular jazz track that’s been covered by many artists since the 1950s. However, one of the most smooth renderings came from Nat King Cole. On the track, Cole describes the feeling of the autumn season and missing someone he loves. As he sings on the first verse, “Since you went away the days grow long / And soon I’ll hear old winter’s song / But I miss you most of all my darling / When autumn leaves start to fall.”

“Wake Me Up When September Ends” is the fourth single from Green Day’s seventh album American Idiot. On the track, the protagonist details how although summer has ended, he wants to move past the month of September because it reminds him of the loss of a loved one. As Billie Joe Armstrong sings on the first verse, “Like my father’s come to pass / Seven years has gone so fast / Wake me up when September ends.”

In 2011, country singer Luke Bryan released his third album Tailgates & Tanlines. One of the album deep cuts is “Harvest Time,” in which Bryan details what the fall season brings in his town. His love for the season is on full display from the first verse as he sings, “There’s peanut dust and corn husks drifting through the air tonight / The marching band’s warming up under the football lights.” 

One of Wyclef Jean’s most popular songs in his solo discography is his 1997 single “Gone Till November.” On the track, Jean reflects on people who take on side hustles, end up leaving home, and are unsure when they will be returning. As he says on the hook, “Yo, tell my girl, yo I’ll be gone ‘til November / January, February, March, April, May / I see you crying, but girl, I can’t stay.”

Chris Brown reflects on the changing of seasons on his 2014 track “Autumn Leaves.” Brown realizes that his relationship with his lover seems to be fading, his partner wants to leave and he’s trying to save it. As he says on the first verse, “If you leave this time, I fear that you’ll be gone for good, so / And I hold on like leaves in fall to what is left.” 

In 1996, Fiona Apple released her debut album Tidal. In addition to the six singles she released, one of the fan favorites included “Pale September.” On the track, Apple describes how autumn not only changes her mood, but it also reflects where she is in her relationship. 

One thing that defines how autumn is finally upon us is knowing football season is back. Country singer Kenny Chesney sets the scene perfectly on his 2010 track “The Boys of Fall.” It’s evident from the first verse as he says “When I feel that chill, smell that fresh cut grass / I’m back in my helmet, cleats and shoulder pads / Standing in the huddle listening to the call / Fans going crazy for the boys of fall.” 

John Coltrane and Johnny Hartman teamed up on their 1963 track “Autumn Serenade.” On the track, they detail how love can fade at times. Their feelings are displayed throughout the track singing, “Love was ours until October wandered by / Let the years come and go / I’ll still feel the glow that time cannot fade / When I hear that lovely autumn serenade.” 

In 2017, Tyler, The Creator released his critically-acclaimed fourth album Flower Boy. On the track “November,” Tyler describes the month as a great time in his life while also reflecting on some of his insecurities and his desire to get back into a better headspace. As he says on the hook, “Take me back to November / Take me back to November / Hawaiian shirts in the winter, cold water, cold water, / Yeah, take me back to November, wassup.” 

Yebba’s 2021 ballad “October Sky” reflects on moments of dealing with loss and grief in her life. The singer has been open about losing her mother several years ago, and “October Sky” seems to reflects on memories of her. As she sings on the first verse, “So we fell through the door like the autumn leaves / And I wrestled my brother down to his knees / Just to watch as her rocket shot in the October sky.” 

“Autumn in New York” has been covered by a number of artists over the years, but one of the most popular versions came in 1949 from Frank Sinatra. On the track, Sinatra details what the fall season looks like in the Big Apple. As he starts the song with, “Autumn in New York / Why does it seem so inviting / Autumn in New York / It spells the thrill of first knighting.” 

On Neil Diamond’s 1979 track “September Morn,” the singer reflects on a time that made him feel good and at ease with his lover. As he says on the hook, “September morn / We danced until the night became a brand new day / Two lovers playing scenes from some romantic play.” 

An autumn leaf falling typically symbolizes that new life and growth is taking shape. That’s the indication that Ed Sheeran takes on his 2011 track “Autumn Leaves” to describe the death of someone close to him. As he sings on the hook, “Do you ever wonder if the stars shine out for you? / Float down, like autumn leaves / Hush now, close your eyes before the sleep / And you’re miles away / And yesterday you were here with me.” 

On Neil Young’s 1992 track “Harvest Moon,” the singer reflects on the relationship with his beloved. Young pays tribute to his wife to show his love and admiration for her. As he says on the hook, “Because I’m still in love with you / I want to see you dance again / Because I’m still in love with you / On this harvest moon.” 

In 2013, alternative band The Neighbourhood released its debut single "Sweater Weather." On the track, the band details how California doesn't always get the coldest, but sometimes the state is perfect for the right sweater and being able to use it as comfort with a loved one. 

Damian Marley reflects on how people go through ups and downs in life, and the importance of keeping the faith on his 2017 track “Autumn Leaves.” He mentions how times are constantly changing as new seasons come around. As Marley says on the first verse “Oh autumn seems to never end / Leaves are always brown / Summer seems to never tend / To ever come around.” 

On Daughtry’s 2009 track “September,” the band reflects on how the seasons change and to appreciate time in the present. As they sing on the hook, “Of all the things I still remember / Summers never look the same / The years go by and the time just seems to fly / But the memories remain.” 

Sometimes in order for people to feel centered and more like themselves, they have to return to what’s familiar to them. James Taylor reflects on returning home on his 2002 track “October Road.” His feelings of home comfort shines throughout the track as he sings, “Well Imma going back down maybe one more time / Deep down home, October road / And I might like to see that little friend of mine / That I left behind once upon a time.” 

On SiR’s “Summer in November, “ he describes the love and beauty from a partner being so dear and joyous to him. He uses summertime in November as a metaphor to describe his love interest. As he sings on the hook, “You’re summer in November, darlin’ / You’re something to remember, darlin.’”