23 Best Songs About Regret, Guilt, & Mistakes
Everyone has experienced regret in life, so you’ll likely relate to these songs.
Artists from country to rock have written countless songs about regret, loss, and guilt.
The truth is we all have experienced these emotions at some point in our lives, whether they stemmed from broken relationships, missed opportunities, or unexpected losses.
We’ve gathered these greatest hits to remind you that you’re not alone when regretting past mistakes or situations.
The 23 Best Songs About Regret
Listening to music can offer comfort during troubling times. We hope you can relate to these special tracks no matter what you’re going through.
So, let’s dive in. Here’s our playlist of the 23 best songs about regret:
23. Sorry – Justin Bieber
“Sorry” is a catchy hit from Justin Bieber’s fourth studio album, Purpose, which was introduced to the world in 2015.
The dance-pop tune is a desperate plea for forgiveness that expresses JB’s regret for mistreating his old lover.
“Sorry” was a worldwide hit, topping the Canadian Hot 100, U.S. Billboard Hot 100, and Mexican Airplay charts in 2015.
22. Somebody That I Used To Know – Gotye ft. Kimbra
This alternative rock song was released from Gotye’s third studio album, Making Mirrors, in 2011.
“Somebody That I Used To Know” features a man reminiscing about one of his past relationships and what led to a terrible breakup.
The tune won a Grammy Award for Best Pop Duo/Group Performance and Record of the Year in 2013 and topped charts worldwide, from Hungary to New Zealand.
21. All Apologies – Nirvana
“All Apologies” is an intriguing song from Nirvana’s final studio album, In Utero, in which lead singer, Kurt Cobain, apologizes to his wife and daughter for his failures as a husband and father.
If you love Nirvana and are interested in hearing more from them, check out our best 90s songs playlist, which features their hit. “Smells Like Teen Spirit.”
The track reached #32 on the UK Singles chart and received two Grammy nominations for Best Rock Performance by a Duo or Group with Vocal and Best Rock Song in 1995.
20. When The Party’s Over – Billie Eilish
This dark pop track was released from Billie Eilish’s debut studio album, When We All Fall Asleep, Where Do We Go? in 2019, but was actually released first in 2018.
“When The Party’s Over” features a girl who wants to end the relationship with her significant other, but he doesn’t seem to get the hint due to miscommunication.
The hit made it to #29 on the Billboard Hot 100 and #21 on the UK Singles chart between 2018 and 2020.
19. Regret – New Order
“Regret” quickly became one of New Order’s most popular songs in the early 1990s and was released from their sixth album, Republic.
Although the lyrics are up for interpretation, many believe this tune is mainly about the difficulties of living life as a celebrity in the public eye.
This alternative rock song was a commercial success, taking the #28 spot on the Billboard Hot 100 and placing #1 on the Billboard Dance Club Songs chart in 1993.
18. Hard To Say I’m Sorry – Chicago
Here’s a power ballad that’s fit for a lonely night after you’ve made a sincere apology, but it doesn’t do any good.
In “Hard To Say I’m Sorry,” we see a male narrator attempting to hold onto a meaningful relationship but realizing the sad but bitter truth that there’s nothing he can do to prevent it from ending.
The track won an ASCAP Pop Music Award in the Most Performed Songs category and topped the Billboard Hot 100, Adult Contemporary, and Swiss Singles charts in 1982.
17. I Still Believe In You – Vince Gill
If you’re looking for something more country, this hit from Vince Gill is an excellent addition to your regret playlist.
In the song, Gill apologizes to his significant other for not spending enough time with her, vowing to be better at being her man.
“I Still Believe In You” reached #1 on the Billboard Hot Country Singles & Tracks and Canada Country Tracks charts in 1992.
16. Against All Odds (Take A Look At Me Now) – Phil Collins
Phil Collins wrote “Against All Odds (Take A Look At Me Now)” for the 1984 film of the same name.
This hit describes a man’s inner turmoil after watching his lover leave him and how he longs to wait for her to return to him.
The single topped charts worldwide, including Canada, Norway, and Ireland, and made it to #2 on the Billboard Adult Contemporary chart in 1984.
15. Dancing On My Own – Calum Scott
This pop tune was originally released by Swedish singer-songwriter Robyn in 2001 but was recorded by Calum Scott in 2016.
The lyrics focus on a person watching their former sweetheart dance with someone else at a club.
“Dancing On My Own” was nominated for British Single of the Year at the 2017 Brit Awards and charted #1 in Mexico and Scotland in 2016.
14. If I Could Turn Back Time – Cher
“If I Could Turn Back Time” was released from Cher’s nineteenth album, Heart of Stone, in 1989.
This pop-rock track talks about a woman’s remorse after making hurtful remarks and ruining an important relationship in her life.
The tune peaked at #3 on the Billboard Hot 100 and reached #1 on the Billboard Adult Contemporary chart between 1989 and 1990.
13. Nothing Compares 2 U – Sinéad O’Connor
Although Prince originally wrote this tune in 1985, Sinead O’Connor recorded her version in 1990.
This emotional ballad describes a woman’s extreme pain and loneliness after parting ways with her significant other.
“Nothing Compares 2 U” won Best Female Video at the MTV Video Music Awards in 1990 and charted #1 in seventeen countries.
12. Stay With Me – Sam Smith
As one of the most popular singers in the world, Sam Smith has earned quite a name for himself, and it all started with this hit from his debut album!
“Stay With Me” talks about a man’s lacking love life, where he falls for someone who doesn’t feel the same about him.
The song topped the Canadian Hot 100 and the U.S. Billboard Mainstream Top 40 between 2014 and 2015.
11. Someone You Loved – Lewis Capaldi
“Someone You Loved” is the perfect song to listen to after a bad breakup, especially because of Lewis Capaldi’s raw and powerful vocals.
The piano ballad focuses on the male narrator’s regret of losing his lover and expressing the pain of missing her.
This hit reached #1 on the UK Singles chart and won Song of the Year at the Brit Awards in 2020.
10. Waves – Dean Lewis
Australian singer-songwriter, Dean Lewis, released this hit from his debut EP, Same Kind of Different, in 2017.
The lyrics talk about how life is unpredictable and ever-changing,g and it becomes less exciting as time moves on.
“Waves” earned the #1 spot on the Australian Artist Singles chart and #21 on the Billboard Adult Top 40 between 2016 and 2020.
9. Please Forgive Me – Bryan Adams
This popular single comes from Bryan Adams’ greatest hits compilation album, So Far So Good, and discusses his unending love for his sweetheart.
If you’re a fan of Bryan Adams, check out our best 80s songs playlist, which includes his famous track, “Summer Of ’69.”
“Please Forgive Me” charted #2 on the UK Singles and the Billboard Adult Contemporary chart in 1993.
8. The Living Years – Mike + The Mechanics
This soft rock hit will encourage you to spend quality time with your loved ones while they are still around.
“The Living Years” features a son who regrets an unresolved argument with his father,r who had passed away.
In 1989, the song won the Ivor Novello Award for Best Song Musically and Lyrically and received four Grammy nominations in 1990.
7. Please Remember Me – Tim McGraw
“Please Remember Me” was originally recorded by Rodney Crowell in 1995 but was covered by Tim McGraw in 1999.
This relatable song speaks of a broken romantic relationship, where the man wishes the best for his former lover and asks her to remember him.
McGraw’s version topped the Billboard Hot Country Singles & Tracks chart and peaked at #10 on the Billboard Hot 100 in 1999.
6. Fire And Rain – James Taylor
Here’s a folk-pop song from James Taylor that’ll surely bring you to tears.
“Fire And Rain” comes from Taylor’s second album, Sweet Baby James, and talks about his life’s highs and lows, from losing a good friend to recovering from drug addiction in rehab.
The track charted at #4 on the U.S. Cashbox Top 100 and #2 on the Canada Top Singles chart in 1970.
5. Back To December – Taylor Swift
“Back To December” released this country pop hit from her third studio album, Speak Now, in 2010.
The lyrics describe how much regret Swift has over a relationship she messed up in her past, resulting in broken trust between her and her now ex-boyfriend.
“Back To December” peaked at #3 on the Hot Country Songs chart and #6 on the Billboard Hot 100 in 2010.
4. I Will Follow You Into The Dark – Death Cab For Cutie
If folk rock is more your style, you’ll appreciate this hit from Death Cab For Cutie.
“I Will Follow You Into The Dark” features a male narrator talking about his love for his romantic partner and how he believes they’ll reunite after death.
The somber acoustic ballad earned the #34 spot on the Billboard Adult Top 40 and #6 on the UK Rock & Metal chart in 2006.
3. Hurt – Johnny Cash
Johnny Cash is one of the best country singers with a deep voice, and “Hurt” is among his greatest hits of all time.
“Hurt” is originally a Nine Inch Nails song written about Cash’s struggles with drug addiction and how he regrets hurting the people in his life.
The track reached #33 on the Billboard Alternative Airplay chart in 2003, and the music video won a Grammy for Best Short Form Music Video in 2004.
2. Tears In Heaven – Eric Clapton
Prepare your heart for this rock song, which appears in the soundtrack for the 1991 film Rush.
The lyrics describe the pain Clapton felt after the sudden loss of his young son after he fell out of a New York City apartment window.
This sad tune won a Grammy Award for Best Male Pop Vocal Performance, Record of the Year, and Song of the Year in 1993 and earned the #1 spot on charts worldwide, from Canada and Ireland to Poland and the U.S.
1. Supermarket Flowers – Ed Sheeran
“Supermarket Flowers” is a pop ballad from Ed Sheeran’s 2017 album, ÷, which talks about his grandmother, Anne, on the day she passed.
If you’re an Ed Sheeran fan, we suggest taking a look at our best songs of all time playlist, which features his mega-hit, “Shape Of You.”
The heartbreaking song earned the #8 spot on the UK Singles chart and #75 on the Billboard Hot 100 in 2017.
We hope you’ve enjoyed these songs about regret and that they make a great addition to your go-to playlist.
We chose “Supermarket Flowers” by Ed Sheeran as the #1 track because of its incredibly relatable lyrics, beautiful melody, and massive success worldwide.
Let these tunes remind you to live fully and appreciate your loved ones while they’re here!
What’s the best song about regret, in your opinion? Leave a comment below.
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