Top 50 Songs about Regret

It’s an unusual person or a psychopath that doesn’t have some kind of regret in their past. It could be regret of love lost, which it often is, a missed opportunity, or maybe just something we wished we’d done better.

Regardless, it’s a fertile ground for music and musicians. Therefore, there are plenty of songs about regret, and there are thousands to choose from if you’re feeling reflective.

But I’ve narrowed the selection down for you, so let’s get started and take a look at the first song about regret…

Top 50 Songs about Regret

1 Cat’s in the Cradle by Harry Chapin

This is such a powerful song to start with. It’s a lyrical masterpiece that has stood the test of time. The message it conveys has in no way been diminished with time. It’s as relevant today as it’s ever been.

So, what is it all about?

“Cat’s in the Cradle” is concerned with the relationship between a father and son. The son looks up to this father as a role model and frequently expresses the sentiment of wanting to be just like him.

During the first half of the song, the father misses major milestones of his son growing up and has little time to spend with him. He’s always too busy; consequently, he lets his son down by not spending any significant time with him.

In the second half of the song… 

His son begins college and then moves away. At this point, the tables turn. The father wants to spend time with his son, but now, his son is too busy with his own life to spare time with his father. He professes to still want to be like his dad, which is ironically what is happening.

The song sends out a strong message not to take your loved ones for granted, no matter how busy you are. The fact is that this is even more important when your children are growing up. Those years go incredibly quickly, as any parent will tell you.

“Cat’s in the Cradle” was released in 1974 and made it into the Top 10 in both the US and the UK. Sales were steady but not stellar. However, it received widespread critical acclaim and won a Grammy. Plus, in 2001, it was inducted into the Grammy Hall of Fame. 

2 I Want You Back by Jackson 5

The song was released in 1970 by the Motown label. Those were exciting times for Soul and music in general. During the late 60s and early 70s, Motown was making history with some of the greatest Soul releases ever to be heard.

“I Want You Back” has all the wonderful ingredients of a Motown classic recording. It has a driving bass line and amazing Gospel-style harmonies. 

Also thrown into the mix are fantastic funky guitar riffs and Michael Jackson’s peerless vocals. What’s more, if you watch the video, you get all of this plus synchronized dancing. 

What’s not to like?

It’s a song about a guy who takes his girl for granted and eventually ends up losing her. It’s inferred that he did little to prevent the process. However, in the future, he sees his ex with another guy and realizes he still has feelings for her.

It’s at this point that he regrets his behavior and comes to the understanding that he loves her and wants her back. Much of the song is then dedicated to him pleading his case.

The song became a #1 hit, which was a first for the band. Additionally, they also got to perform it live on the Ed Sullivan Show, which was another first.

One thing I especially like about the song…

The contrast between the song’s lyrical content and the high-tempo and happy delivery. It’s something that makes you want to dance despite the misery of the poor guy in the song.

At the time “I Want You Back” was released, Michael Jackson was only twelve years old. It is a complete credit that his vocal performance was convincing about a subject he couldn’t possibly understand or have any experience with.

He should have been at school.

3 If I Could Turn Back Time by Cher

I’m sure the irony of the song’s title isn’t missed by any of you. Because let’s face it, if anyone has tried to turn back time, then Cher should be up there as having given it a good go. 

I’m honestly not judging her. I say good for her if she wants to take her chances with eternal youth at the hands of Beverly Hills surgeons.

But I digress…

The song was released in 1989 and will probably be as much remembered for the iconic music video as the song. The video was shot at Long Beach on the deck of the USS Battleship Missouri. 

Cher sang the song very provocatively, in a sheer black jumpsuit, to the ship’s crew. Luckily, she hid the more intimate parts of her body, though only just. Interestingly she wore a similar, though updated dress, in 2014, and I swear she looked younger. 

Maybe Cher can turn back time after all…

The song reached #1 in the US. The album it was taken from, Heart of Stone, only reached #10 but was a much bigger success, selling over three million copies in the US alone.

“If I Could Turn Back Time” is almost always included in her live shows and is a firm fan favorite. However, if you want to see her live, you’d better act fast. She is playing again in Vegas but may only be there for another 50 years.

4 Sorry Seems to be the Hardest Word by Elton John

This a great song about having regrets from the writing partnership of Elton John and Bernie Taupin. It was released in 1976 and taken from the album Blue Moves. The single and album chartered reasonably well, but the sales were a little disappointing.

That’s hardly surprising as far as the album is concerned, but maybe a little for the single. Quite honestly, at this point in his career, the best days were behind him. 

You have to go back to 1973, when he released two of his greatest albums. Don’t Shoot Me I’m Only the Piano Player, and Goodbye Yellow Brick Road to find the real Elton John magic.

As far as Blue Moves goes… 

The only decent single on the entire album is “Sorry Seems to be the Hardest Word.” It’s hardly a ringing endorsement for a double album with eighteen tracks.

“Sorry Seems to be the Hardest Word” is a good enough tune with a great melody. However, the lyrics feel a little depressing and not as good as most of his other songs. A lot of songs about regret can be sad, but Taupin seems to have gone overboard here. 

It’s all about trying to recapture a lost love and the lengths the singer is prepared to go to salvage things. This is all well and good, but the extremes and gestures go on and on. It’s a good song dealing with regret, but it’s just not one of Elton John’s best.

5 Baby Can I Hold You by Tracy Chapman

Tracy Chapman is an incredible artist and wrote a host of incredible songs. I count this as one of them, along with “Fast Car,” “Talkin’ Bout a Revolution,” and “If Not Now..”. It’s hard to believe that these three songs came from her 1988 debut album, Tracy Chapman.

In a world seemingly obsessed with electronic and complex music, these simple yet powerful songs hit people’s imaginations and consciousness hard. She spoke to a generation with nothing more than an acoustic guitar and her voice. 

Subsequently, she enjoyed commercial success. Her debut album sold 20 million copies worldwide and received widespread critical acclaim. And her first album justly won three Grammy Awards.

So, what about this song?

“Baby Can I Hold You” is a song about a woman reflecting on her mistakes in a relationship. She wishes she could go back and be able better express herself to her partner. The singer knows that this isn’t possible and acknowledges it. She also accepts that she still has difficulties in the present in terms of showing and expressing her emotions.

It feels like both regret and sadness for the past, with determination for the future to do better.

6 Hurt by Johnny Cash

This is a powerful regret song that found its way from the world of Industrial Metal to Country.

How?

It was originally written by Trent Reznor, the lead singer and mastermind behind Nine Inch Nails, a Hard Rock/Hard Metal band who are often referred to as being Industrial. There is no doubt that their music is intense, and frankly, a little too much so for my liking.

However, what is to my liking is the song. It is brilliantly well-crafted. “Hurt” was first released by Nine Inch Nails in 1995 from their album, The Downward Spiral. It received much critical acclaim and achieved two million downloads as well as a nomination in 1986 for a Grammy.

Then came Johnny Cash…

His cover was unbelievable. The music video that went with it was one of the best in history. Something the Grammy’s recognized as the video won one of their highly prestigious awards. The British public was also impressed, voting it the second-best cover of all time.

Johnny Cash’s version came just a few months before his death. You can even see in his performance that his life was very near the end. Despite this, he honestly put in a performance of a lifetime, making it possibly his best song.

That’s some achievement given his long and illustrious career…

Johnny Cash interprets the song through the video by focusing on his past. This includes time spent on this musical career and time spent with his family. The overall impression is one of remorse for the wasted time in this life following money and fame rather than concentrating on his family.

The message is that when the end comes, family is what matters, and everything else is nothing. As far as songs about regret go, it’s one of the most powerful. 

7 Release Me by Engelbert Humperdinck

Is this the ultimate regret song? I think it probably is, which is why I’ve saved it till last. It is an old song and dates right back to 1949 when it was initially released by Eddie Miler, who was also the songwriter. 

Few will know this original version. Although, there are also very few who are likely to have heard the 1967 Engelbert Humperdinck cover. 

The Engelbert Humperdinck 1967 “Release Me” was very popular in the UK, enough so to reach #1. No doubt a lot of you older guys and girls will remember it. What a lot of you may also remember is the rather soothing melody rather than the brutal lyrics.

So, how vicious are the words?

They’re honestly on another level. The song is straight to the point and doesn’t mince words. It lays down the facts that the singer doesn’t love his partner and wants them to leave them. I can’t think of any other songs of regret that are so matter-of-fact.

It never ceases to amaze me that “Release Me” was so popular, given its harsh nature. Maybe we were all much more straightforward back in the 60s. 

Alternatively, maybe there were a lot of people in trapped relationships who could relate to the song. Or, it could be that people had never even bothered to listen to the words and just loved the tune.

8 Landslide by Fleetwood Mac

9 The A Team by Ed Sheeran

10 Yesterday by The Beatles

11 Tears in Heaven by Eric Clapton

12 Say You Love Me by Fleetwood Mac

13 In the Ghetto by Elvis Presley

14 Wrong by Depeche Mode

15 I Will Remember You by Sarah McLachlan

16 Love Will Tear Us Apart by Joy Division

17 The Freshmen by The Verve Pipe

18 I Wish I Was Sober (But I Hate Being Sober) by Frightened Rabbit

19 The One That Got Away (Acoustic) by Katy Perry

20 It’s Hard to Be a Saint in the City by Bruce Springsteen

21 This Is What It Feels Like (feat. Trevor Guthrie) by Armin van Buuren

22 Between the Bars by Elliott Smith

23 I Don’t Want to Be a Bride by Vanessa Carlton

24 Why Didn’t You Stop Me? by Mitski

25 A Lack of Color by Death Cab for Cutie

26 The Way We Were by Barbra Streisand

27 The Sound of Silence by Simon & Garfunkel

28 The Living Years by Mike + The Mechanics

29 Un-Break My Heart by Toni Braxton

30 Dust in the Wind by Kansas

31 Behind Blue Eyes by The Who

32 My Heart Will Go On by Celine Dion

33 Losing My Religion by R.E.M.

34 What It Takes by Aerosmith

35 Streets of Philadelphia by Bruce Springsteen

36 Angie by The Rolling Stones

37 Long Long Way to Go by Phil Collins

38 The One I Love by R.E.M.

39 In the End by Linkin Park

40 Everything I Wanted by Billie Eilish

41 Apologize by OneRepublic

42 Stressed Out by Twenty One Pilots

43 Heart-Shaped Box by Nirvana

44 Hurt by Nine Inch Nails

45 Regret by New Order

46 Fade Into You by Mazzy Star

47 The Scientist by Coldplay

48 All I Want by Kodaline

49 Dancing on My Own by Robyn

50 Rehab by Amy Winehouse

Searching for Songs of Sorrow?

Well, take a look at our detailed reviews of the Best Songs About Pain & Suffering, the Best Songs About Crying, the Best Songs About Loneliness, the Best Breakup Songs, and the Best Songs About Anxiety for more emotional song selections.

Also, you’ll need to listen to those songs. So, check out our in-depth reviews of the Best True Wireless Earbuds, the Best Sound Quality Earbuds, the Best Headphones for Music, the Most Comfortable Headphones, and the Best Headphones Under $200 you can buy in 2023.

Songs about Regret – Final Thoughts

So, there you have it. I hope you enjoyed these songs about feeling regret and the accompanying trip down the well of woe. However, try not to get too down. We all make mistakes, and it’s not about how many times you get knocked down, but how many times you pick yourself back up.

Keep on moving forward and happy listening.