21 Songs About Retirement (2023)

People commonly associate the term “retirement” with a person’s final exit from the workforce. However, this term can mean much more than just that. To “retire” also means “to withdraw” from something, whether that something is a person, a place, or a situation.

Moreover, retirement is so emotionally charged that lots of songs have been written about it. So, if you are looking for songs about retiring, in whatever form that word may take, below is a list of the 21 best songs about retirement that you should listen to:

21. Retirement Song — The Longest Johns

We’ll start with a song about the traditional meaning of retirement: “Retirement Song,” by a British folk group named The Longest Johns. It’s a cappella music but is already catchy enough because of its fun tune and creative lyricism. This folk track from Bones in the Ocean will have you clapping along as they sing about the kind of life they will lead after retiring.

20. The Best Is Yet to Come —  Count Basie and Frank Sinatra

Frank Sinatra, one of the most in-demand artists of all time, sang his rendition of “The Best Is Yet to Come.” It’s a collaboration with Count Basie’s Orchestra recorded on his 1964 album It Might as Well Be Swing, and it’s the last song Sinatra ever performed live before his death, making it a truly remarkable piece. Listening to this jazz track is like taking a breath of fresh air.

19. This Ain’t Goodbye — Train

Save Me, San Francisco is an album introduced by Train. One of the songs is a heartfelt ballad, “This Ain’t Goodbye.” The song’s lyrics are about two people who were like “stars up in the sunlit sky” but were ultimately destined to be apart. The emotion behind his voice will not fail to get you every time you listen to it.

18. Hello, Goodbye — The Beatles

Here’s The Beatles’ live performance of their popular hit “Hello, Goodbye” from their album Magical Mystery Tour. Despite the fact that the lyrics to “Hello, Goodbye” only consist of a handful of words, the song has stood the test of time and is still considered one of the most beloved classics by many. This soothing folk tune from 1967 is a pure pleasure for the ears, and that’s why.

17. 100 Years — Five for Fighting

It’s impossible not to reflect on one’s entire life when contemplating retirement. Five for Fighting’s “100 Years” incredibly captures that inexpressible mix of nostalgia for the past and hope for the future. The heavy words and the mellow melody of this track, which can be found on his 2006 album called Two Lights, will leave you feeling emotional and contemplating life.

16. When I’m 64 — The Beatles

Another song by the Fab Four makes the cut. The Beatles’ “When I’m 64” appeared on their 1967 album The Beatles Golden Edition. The song describes a love that is as gentle and quiet as the calm ocean waves, rather than a roller-coaster-like one. This soft rock classic “When I’m 64” will remain in your memory forever after hearing it.

15. (I’ve Had) The Time of My Life — Bill Medley and Jennifer Warnes

With so many artists having their own versions over the years, “(I’ve Had) The Time of My Life” is bound to ring a bell. The 1987 romantic film Dirty Dancing featured this song, which was originally recorded by Bill Medley and Jennifer Warnes. Among the many awards bestowed upon this classic pop tune is an Academy Award for Best Music (Original Song). You will enjoy both listening and dancing to the catchy tune of this song.

14. Closing Time — Semisonic

You will experience a wave of nostalgia as you listen to Semisonic’s “Closing Time.” This rock tune is from their 1998 album Feeling Strangely Fine and was nominated for the Billboard Music Award for Modern Rock Track of the Year. It has an infectious song melody with brilliant lyrics that focus on the closing time of a workplace and the closing chapters of life itself as well. 

13. You’ve Got a Friend — James Taylor

James Taylor took home the Grammy Award for Best Male Pop Vocal Performance for his song “You’ve Got a Friend.” It’s a sentimental country-folk song from Mud Slide Slim and the Blue Horizon. It was recorded in 1971, but it will always have the power to melt one’s heart while listening to this masterpiece.

12. It’s Five O’Clock Somewhere — Alan Jackson

Up next is a collaboration of Alan Jackson and Jimmy Buffett, two amazing country singers, for the song “It’s Five O’clock Somewhere.” You’ll definitely relate to this song about how time passes by too slowly while working. So, he leaves work at lunchtime, saying that it’s five o’clock somewhere. This fun and calming country song is the lead single from Jackson’s Greatest Hits Volume II.

11. Good Times Roll — The Cars

“Good Times Roll” by The Cars is a rock song by The Cars, released as the first track from their 1978 debut album The Cars. It talks about not giving a thought to what other people say and instead, just “letting the good times roll.” The repetitive lines and the engaging backing track make it a catchy, feel-good song.

10. Something More — Sugarland

Since burnout is something that the vast majority of us have encountered at some point, listeners will most likely be able to relate to Sugarland’s song “Something More,” which was included in her album Twice the Speed of Life. This country song, which was recorded in 2004, addresses some of the daily challenges that employees face. It also has incredible vocals accompanied by enticing instrumental tones.

9. September — Earth, Wind & Fire

A tasty orchestra performance by Earth, Wind, & Fire is here! “September” is an all-time hit recorded in their The Best of Earth, Wind & Fire, Vol. 1 album in 1978. Because of its joyous arrangement that will surely uplift everyone’s spirits, it got nominated for the CMT Music Award for CMT Performance of the Year. If you’re feeling blue, go listen to this R&B disco song by Earth, Wind & Fire.

8. Champagne Supernova — Oasis

The alternative song “Champagne Supernova” is Oasis’s most well-known and successful recording to date. It was originally released by the band on their 1995 album titled (What’s the Story) Morning Glory? Because of its melancholic atmosphere and profound lyrics about how people and time change in the blink of an eye. You will undoubtedly feel sentimental while listening to this song.

7. Hit the Road Jack — Ray Charles

Ray Charles recorded an infectious song called “Hit the Road Jack” for the film Ray. It was recorded in 1961 and eventually won the Grammy Award for Best R&B Performance. The song’s lyrics and title are about telling a certain man named Jack to leave and never return. The pitch-perfect vocals and masterfully-played instruments make it a superb classic song!

6. Feeling Good — Michael Bublé

The song “Feeling Good” by Nina Simone is one of the most recorded songs of all time. Michael Bublé’s version, recorded for the film titled Memories of Matsuko, is one of the most famous. This jazz-pop piece is about withdrawing from the past and celebrating the current happiness he feels. It’s the kind of tune with a cheerful, inspiring vibe that really appeals to listeners.

5. Can’t Take It With You — The Allman Brothers Band

Another classic favorite is up next. It’s “Can’t Take It With You,” performed by The Allman Brothers Band. It is part of Enlightened Rogues, the sixth studio album by the American rock band. This old-school rock tune is beloved not only for its clever lyrics by Dickey Betts, Don Johnson, and Forest Richard Betts but also for its infectiously upbeat melody and instrumentation.

4. Take This Job and Shove It — Johnny Paycheck

Johnny Paycheck’s country track, “Take This Job And Shove It.” It is the title track of his 1977 album. From the title itself, you can already tell that he sings about quitting his job, which makes him unhappy. This track was nominated for the Country Music Association Award for Song of the Year. It has an authentic country vibe that will make anyone going through a similar experience feel heard.

3. Good Riddance — Green Day

The opening guitar strums set a touching mood for Green Day’s song “Good Riddance.” Nimrod, the band’s album released in 1997, features this mellow indie song. The song’s lyrics convey that we should cherish each day of our lives and not waste any of those precious moments. Awards and nominations for various MTV Music Awards were also bestowed upon this achingly beautiful tune.

2. I’m Free — The Rolling Stones

One more song that can magically transport you back to the past is “I’m Free” by The Rolling Stones. It was produced for the musical movie titled Shine a Light. This song has that rock and blues style, with lyrics that go like this:

I’m free to do what I want any old time
So love me, hold me, love me, hold me
I’m free any old time to get what I want

It emphasizes the liberty that comes with retirement. This song is undoubtedly an enjoyable piece to listen to while you are enjoying your weekend or vacation.

1. 9 to 5 — Dolly Parton

We’re almost closing! Our last track is Dolly Parton’s “9 to 5” from her 9 to 5 and Odd Jobs album. She discusses the disparities in the working class, along with her frustrations and aspirations. This work has been honored with a number of Grammys, including Best Country Song and Best Female Country Vocal Performance. It’s an enjoyable way to express your frustrations because of the upbeat music and Dolly Parton’s gentle country vocals.

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