29 Best Songs About Regret: A Heartbreaking Playlist

We've all been there – that gut-wrenching feeling of "what if?" The echoes of past decisions, the missed opportunities, the words left unsaid. These are the raw emotions that fuel some of the most powerful and unforgettable songs ever written. If you're searching for the perfect soundtrack to those moments of reflection, you've come to the right place. This curated list explores the best songs about regret, delving into the heart-wrenching lyrics and melodies that capture the complexities of looking back. From soulful ballads to anthemic rock anthems, we’ve compiled a collection that resonates with the universal experience of remorse and the longing for a second chance. Whether you’re processing your own regrets or simply appreciate emotionally resonant music, this exploration of the best songs about regret will leave you feeling seen, understood, and maybe even a little bit less alone. Prepare to revisit the past through the lens of some truly exceptional artistry.

29 Best Songs About Regret: A Heartbreaking Playlist
SongArtistAlbumListens
1. Sorry Justin Bieber Purpose (Deluxe) 4B+
2. Hello Adele 25 3B+
3. Someone Like You Adele 21 2B+
4. I Will Always Love You Whitney Houston The Bodyguard - Original Soundtrack Album 2B+
5. The Scientist Coldplay A Rush of Blood to the Head 1B+
6. Creep Radiohead Pablo Honey 1B+
7. Boulevard of Broken Dreams Green Day American Idiot 815M+

1. Sorry

Heartbreakingly Honest Lyrics: "Sorry" lays bare Bieber's remorse with raw vulnerability, detailing the pain of his actions and the desire for forgiveness, making it deeply relatable for anyone grappling with regret.

Poignant Melody: The song's melancholic melody and stripped-down instrumentation amplify the emotional weight of the lyrics, creating a soundscape perfectly suited to the feelings of regret.

Vocal Performance: Bieber's vocal delivery is filled with genuine emotion, conveying the depth of his sorrow and adding to the song's overall impact. The sincerity in his voice is what truly sets this track apart.

Sorry - Justin Bieber

2. Hello (25)

Adele's Vocals: Adele's raw, emotionally resonant vocals perfectly capture the heartbreak and longing inherent in regret, making the listener feel the weight of the past.

Lyrical Depth: The lyrics poignantly explore the complexities of lost connection and the yearning for a second chance, resonating deeply with anyone who has experienced the sting of regret.

Emotional Resonance: "Hello" transcends a simple break-up song; its vulnerability taps into universal feelings of regret and the desire for reconciliation, creating a powerful emotional impact.

Hello - Adele

3. Someone Like You

Adele's Vocals: Adele's raw, emotive vocals are the heart of "Someone Like You" conveying a depth of heartbreak and regret that resonates deeply.

Emotional Resonance: The song's minimalist arrangement, focusing on piano and vocals, allows the intense emotion to take center stage, creating a powerful and unforgettable listening experience perfectly suited to exploring the theme of regret.

Lyrical Honesty: The lyrics are brutally honest and relatable, capturing the painful acceptance of a lost love and the lingering sense of "what if?" This makes it a powerful example of regret in song.

Someone Like You - Adele

4. I Will Always Love You (Whitney Houston)

Vocal Performance: Whitney Houston's powerhouse vocals convey a depth of sorrow and acceptance, making the regret palpable and deeply affecting.

Lyrical Content: The lyrics poignantly capture the bittersweet ache of letting go of a love, highlighting the lasting impact of past choices.

Emotional Resonance: Its raw emotionality transcends generations, making "I Will Always Love You" a timeless anthem for anyone grappling with the complexities of regret.

I Will Always Love You - Whitney Houston

5. The Scientist

Haunting Melody: Coldplay's "The Scientist" features a melancholic piano melody that perfectly encapsulates the feeling of deep regret and longing for a chance to undo past mistakes.

Chris Martin's Vocals: Martin's emotive vocals, filled with vulnerability and sorrow, convey the weight of regret with raw honesty, making the listener deeply connect with the song's emotional core.

Lyrical Depth: The lyrics explore themes of lost love and missed opportunities with poetic imagery and self-reflection, leaving a lasting impression that resonates long after the song ends.

The Scientist - Coldplay

6. Creep (1992)

Sound: Radiohead's "Creep" opens with a raw, almost unsettlingly quiet verse before building to a powerful, distorted chorus – a dynamic tension reflecting the song's emotional turmoil.

Vocals: Thom Yorke's pained, vulnerable vocals perfectly capture the feeling of deep regret and self-loathing, making the listener instantly empathize with the singer's internal conflict.

Emotional Impact: The song's raw honesty and its exploration of inadequacy and social awkwardness resonate deeply with listeners who have experienced similar feelings of regret and self-doubt, making it a timeless anthem of self-reflection.

Creep - Radiohead

7. Boulevard of Broken Dreams (2004)

Haunting Melody: Green Day masterfully crafts a melancholic melody that perfectly encapsulates the weight of past mistakes and lost opportunities, creating a soundscape of regret.

Billie Joe Armstrong's Vocals: Armstrong's raw and emotionally charged vocals convey a deep sense of longing and self-recrimination, making the listener feel the singer's pain.

Lyrical Depth: The lyrics paint a vivid picture of a broken life, full of missed chances and the lingering sting of what could have been, making the song deeply relatable for anyone grappling with regret.

Boulevard of Broken Dreams - Green Day

8. Apologize (2006)

Haunting Vocals: Ryan Tedder's emotive vocals perfectly capture the raw pain and vulnerability of sincere regret, making the listener feel the weight of the apology.

Soulful Melody: The song's memorable melody, combined with Timbaland's signature production, creates a bittersweet soundscape that enhances the emotional impact of the lyrics.

Relatable Lyrics: "Apologize" resonates deeply because of its honest and relatable depiction of remorse and the desire for forgiveness, making it a powerful anthem for anyone grappling with past mistakes.

Apologize - Timbaland,OneRepublic

9. Sorry Not Sorry (Tell Me You Love Me)

Vocal Performance: Demi Lovato's powerful vocals perfectly capture the raw emotion of regret, conveying both defiance and vulnerability in her delivery.

Anthemic Quality: The song's driving beat and empowering lyrics make it a cathartic listen for anyone grappling with past mistakes and their consequences.

Lyrical Honesty: "Sorry Not Sorry" doesn't shy away from the complexities of regret, acknowledging the hurt caused while simultaneously embracing self-acceptance.

Sorry Not Sorry - Demi Lovato

10. Nothing Compares 2 U (1990)

Haunting Vocals: Sinéad O'Connor's raw, emotionally charged delivery is the song's core, conveying a depth of sorrow and longing that resonates deeply with the listener's sense of regret.

Minimalist Arrangement: The sparse instrumentation allows O'Connor's voice to take center stage, amplifying the feeling of vulnerability and the weight of past mistakes.

Timeless Relevance: The song's exploration of lost love and the enduring pain of regret transcends generations, making it a powerfully relatable anthem for anyone grappling with past decisions.

Nothing Compares 2 U - Sinéad O'Connor
  • How Do You Sleep?
    11

    How Do You Sleep?

    Sam Smith

    2019

    In The Lonely Hour

  • Sorry
    12

    Sorry

    Beyoncé

    2024

  • Back to December
    13

    Back to December

    Taylor Swift

    2010

  • What Hurts The Most
    14

    What Hurts The Most

    Rascal Flatts

    2006

    Me And My Gang

  • Tears in Heaven
    15

    Tears in Heaven

    Eric Clapton

    1992

    Rush (Music from the Motion Picture Soundtrack)

  • I Want You Back
    16

    I Want You Back

    The Jackson 5

    1969

    Diana Ross Presents The Jackson 5

  • All Apologies
    17

    All Apologies

    Nirvana

    1993

    In Utero

  • Hard to Say I'm Sorry
    18

    Hard to Say I'm Sorry

    Chicago

    1982

  • If I Could Turn Back Time
    19

    If I Could Turn Back Time

    Cher

    1989

    Heart Of Stone

  • Angie
    20

    Angie

    The Rolling Stones

    1973

    Goats Head Soup (Remastered 2009)

  • Yesterday
    21

    Yesterday

    The Beatles

    1965

    Help! (Remastered)

  • It's Too Late
    22

    It's Too Late

    Carole King

    1971

    Tapestry

  • Father and Son
    23

    Father and Son

    Cat Stevens

    1970

  • I'm Sorry
    24

    I'm Sorry

    Brenda Lee

    1960

  • Regret
    25

    Regret

    New Order

    1993

  • Hurt
    26

    Hurt

    Nine Inch Nails

    1994

    The Downward Spiral

  • Butterfly
    27

    Butterfly

    Weezer

    1996

  • Sorry Seems To Be The Hardest Word
    28

    Sorry Seems To Be The Hardest Word

    Ray Charles,Elton John

    1976

    Genius Loves Company

  • Sorry
    29

    Sorry

    Madonna,BLOND:ISH,Eran Hersh,Darmon

    2005

    True Blue