27 Best Songs About September

21. “September Love” by Kool and the Gang

Song Year: 1983

Kool and the Gang released a slew of danceable hits throughout the mid-1970s and early 1980s. While “September Love” never earned the acclaim or airplay of “Celebration,” the ballad is lyrically poignant.

“September Love” is about growing out of young love. The singer still cares for his former partner, but their relationship is over. “September Love” accepts this reality while mourning it.

22. “September in the Rain” by Dinah Washington

Song Year: 1961

“September in the Rain” is an American standard, written by Harry Warren and Al Dubin in 1937.

Dinah Washington recorded a particularly lovely R&B cover in 1961. The singer’s vocals draw out the poignancy in the heartbroken lyrics. “September in the Rain” laments a lost love and the singer’s inability to move on from the failed relationship.

23. “September Grass” by James Taylor

Song Year: 2001

James Taylor is one of America’s most celebrated poets. Though the singer-songwriter attained fame in 1970, he proved he still had it in 2001 with “September Grass.”

“September Grass” is an ode to memory and youth. Taylor sings about his past with the wisdom of age and experience. While many September songs face the past with melancholy, “September Grass” looks back fondly.

24. “The September of my Years” by Frank Sinatra

Song Year: 1965

Frank Sinatra seemed to have an affinity for songs about September. “The September of my Years”-the singer’s second appearance on this list-finds the singer reflective and thoughtful.

Jimmy Van Heusen and Sammy Cahn composed the Grammy nominee. The narrator of “The September of my Years” finds that having rushed through life, he’s now moved to slow down. As he ages, he wishes he’d taken more time and formed more meaningful relationships.

25. “September Skyline” by Single File

Song Year: 2007

Single File, the short-lived Colorado band, included “September Skyline” on their 2007 album, No More Sad Face.

The mellow emo song has a carpe diem attitude. The lyrics acknowledge change and suggest it should get taken as a catalyst. The narrator encourages their partner to take a chance and commit to the singer.

26. “Maybe September” by Tony Bennett

Song Year: 1966

An American treasure, Tony Bennett, recorded “Maybe September” for his album The Movie Song Album.

Written by Percy Faith, Ray Evans, and Jay Livingston, “Maybe September” is an optimistic song. The lyrics state that despite some setbacks, the narrator still has hope for his life to improve. The upbeat tune inspired several notable covers.

27. “September” by The Shins

Song Year: 2012

Albuquerque’s indie-rock darlings, The Shins, write sunny, relaxed songs. “September” is no exception.

“September” is a hopeful but realistic love song. The beautifully rendered lyrics talk about a healthy relationship between two practical adults. The singer doesn’t have unrealistic expectations; he knows the pair will struggle but believes they can handle their struggles.

Top Songs About September, Final Thoughts

Musicians turn September's sadness into art. These top songs about September use the ninth month as inspiration. These songs use autumn’s onset as a metaphor for fading love and the fleeting nature of time.