10 Best Rock Songs About Regret

In this collection of the 10 Best Rock Songs About Regret, we delve into the various ways in which artists have used music to explore this emotion. From the lament of failed relationships to the remorse over self-destructive choices, each song presents a different facet of regret. For some, it’s about reflecting on “the one that got away,” while for others, it’s the slow realization that their own actions have led them down a path of no return.

# 10 – I Was Only Joking – Rod Stewart

“I Was Only Joking” by Rod Stewart is a standout track from his 1977 album Foot Loose & Fancy Free. Written by Stewart and Gary Grainger, the song showcases Stewart’s signature blend of rock and heartfelt introspection. Released as a single in 1978, it performed well on the charts, reaching No. 5 in the UK as part of a double A-side with “Hot Legs” and making it to No. 22 in the United States.

Read More: Jim Cregan: The ClassicRockHistory.com Interview

# 9 – Story Of My Life – Social Distortion

“Story of My Life” by Social Distortion is one of the most enduring and emotionally resonant songs from their 1990 self-titled album. Written by frontman Mike Ness, the song captures the essence of nostalgia and regret, reflecting on the passage of time and the missed opportunities of youth.  Recorded in 1990 and produced by Dave Jerden, the track showcases Social Distortion’s distinctive sound, a mix of raw punk energy and rootsy Americana influences. Mike Ness’s gravelly vocals are the focal point, accompanied by Dennis Danell on guitar, John Maurer on bass, and Christopher Reece on drums.

Read More: Top 10 Social Distortion Songs

# 8 – Take The Long Way Home –  Supertramp

“Take the Long Way Home” by Supertramp is a reflective and introspective track from the band’s hugely successful 1979 album Breakfast in America. Written by Roger Hodgson, the song delves into themes of personal regret and dissatisfaction, capturing the emotional complexity of feeling like an outsider even within one’s own life. Its lyrics revolve around a protagonist who avoids going home, both literally and metaphorically, because home has become a place of frustration and isolation rather than comfort. In doing so, Hodgson explores the idea of taking the “long way home” as a means of avoiding harsh realities.

Read More: Top 10 Supertramp Songs

# 7 – Your Wildest Dreams – The Moody Blues

“Your Wildest Dreams,” released by The Moody Blues in 1986, stands as one of the band’s most poignant reflections on regret and lost love. Written by Justin Hayward, this track takes listeners on a journey of nostalgia, recalling a long-lost romance and the lingering memories of a first love. The song was featured on the album The Other Side of Life and marked a stylistic shift for the band, embracing synth-pop elements that were popular in the mid-1980s. This was a departure from their earlier, more symphonic and lush sound, but the heart of the song lies in its deeply emotional and relatable lyrics.

Read More: An Interview With John Lodge Of The Moody Blues

https://www.youtube.com/watch?v=kmmPFrkuPq0

# 6 – Aime – Pure Prairie League

“Amie” by Pure Prairie League is one of the defining country rock ballads of the 1970s, encapsulating the theme of regret in a gentle, acoustic-driven sound. Written by Craig Fuller, the song originally appeared on the band’s 1972 album Bustin’ Out. While it was not released as a single until 1975, it garnered significant attention through airplay on college and commercial radio, which led to its eventual success. The song’s retrospective lyrics, combined with its laid-back, melodic style, perfectly convey the emotional uncertainty of a relationship falling apart. Fuller’s vocals, coupled with the band’s harmonies, paint a picture of a love that once was, but is now filled with doubt and hesitation.

Read More: An Interview With Michael Reilly Of Pure Prairie League

# 5 – Debbie Denise – Blue Öyster Cult

“Debbie Denise” by Blue Öyster Cult is a powerful closing track from their 1976 album Agents of Fortune. The song, written by drummer Albert Bouchard and his then-girlfriend Helen Robbins, is a poignant exploration of regret and missed opportunities in love, with its introspective lyrics and gentle melody standing in contrast to some of the heavier material on the album. The narrative of the song centers on a man who, despite the unwavering devotion of his partner Debbie Denise, fails to reciprocate her love fully. He is caught up in his life as a musician, “out rollin’ with [his] band,” unaware of the emotional toll his absence is taking on her. The track was recorded during the Agents of Fortune sessions, which took place in early 1976 at The Record Plant in New York City.

Read More: Eric Bloom of Blue Öyster Cult: The ClassicRockHistory.com Interview

# 4 – Jamie’s Crying – Van Halen

“Jamie’s Cryin’” was released on Van Halen;s 1978 self-titled debut album. Written by David Lee Roth and Eddie Van Halen, the song takes on a more reflective tone compared to the band’s harder rock sound. It tells the story of a young woman, Jamie, who regrets a fleeting romantic encounter, realizing that she desires something more meaningful than a one-night stand. Roth’s dynamic lyrics, combined with Eddie Van Halen’s melodic guitar riffs, create a song that is as emotionally impactful as it is sonically powerful.

Read More: Van Halen’s Best Song On Each Of Their Studio Albums

# 3 – How To Save A Life – The Fray

“How to Save a Life” by The Fray is one of the band’s most iconic and emotional songs, released as the second single from their 2005 debut album, How to Save a Life. Written by lead singer Isaac Slade and guitarist Joe King, the song blends haunting piano melodies with introspective lyrics, addressing themes of loss, regret, and emotional miscommunication. It became a massive hit, reaching number three on the Billboard Hot 100 and topping charts worldwide, resonating deeply with listeners for its raw vulnerability and heartfelt message.

Read More: Top 10 Songs From The Fray

# 2 – Cats In The Cradle – Harry Chapin

It’s amazing how this song just seems to find its way onto so many of our concept song lists. “Cats in the Cradle” by Harry Chapin is one of the most memorable and emotional songs about regret in rock music history. Released in 1974 on Chapin’s Verities & Balderdash album, the song became his only No. 1 hit on the Billboard Hot 100 and remains an iconic narrative about the passage of time and the regrets that come with missed opportunities. Written by Chapin’s wife, Sandra Chapin, and set to Harry’s evocative folk-rock arrangement, the song’s poignant story touches on the strained relationship between a father and his son as life slips by without meaningful connection.

Read More: Top 10 Essential Harry Chapin Songs

# 1 – Nobody’s Fault But Mine – Various

The closing track on our list of the 10 Best Rock Songs About Regret is “Nobody’s Fault But Mine,” a haunting and deeply emotional song that was first recorded by Blind Willie Johnson in 1927. With its lyrics rooted in personal responsibility and spiritual struggle, Johnson’s version of the song carries a distinctly religious tone, suggesting that failure to follow the path of salvation is nobody’s fault but his own. The song has since become a seminal piece of blues history and has been reinterpreted by many artists, including Led Zeppelin, who gave it new life in the 1970s. This was the best track on the last great Led Zeppelin album, entitled Presence. I saw that tour in 1977, and it was life-changing.

Updated September 12, 2025

10 Best Rock Songs About Regret article published on Classic RockHistory.com© 2025

DMCA.com Protection Status

Tom Waits Songs
10 Best Tom Waits Songs Of All Time
INXS Songs
20 Best INXS Songs Of All Time
The Impressions Songs
Top 10 Songs By The Impressions
Scandal Songs
Top 10 Scandal Songs
James Taylor Albums
Top 10 James Taylor Albums
10 Best Sounding Albums Of All Time
10 Best Sounding Albums Of All Time
116 Albums With Identical Titles By Different Artists
116 Albums With Identical Titles By Different Artists
10 Essential Live Rock Albums Composed Of 4 Or More Vinyl LPs
Sammy Hagar To Release "The Residency" Live Album In October
Sammy Hagar To Release “The Residency” Live Album In October
Springsteen Releases Born To Run Outake "Lonely In The Park"
Springsteen Releases Born To Run Outake “Lonely In The Park”
Deftones new album
Deftones Release New Album Private Music, Marking Return After Hiatus
Bobby Whitlock
Bobby Whitlock, Derek and the Dominos Co-Founder and ‘Layla’ Co-Writer, Dies at 77
Ana Popovic Interview
Ana Popovic: The ClassicRockHistory.com Interview
Steve Rothery of Marillion Interview
Steve Rothery of Marillion: The ClassicRockHistory.com Interview
Robin Batteau: The ClassicRockHistory.com Interview
Robin Batteau: The ClassicRockHistory.com Interview
Gordon Giltrap Interview
Gordon Giltrap: The ClassicRockHistory.com Interview
The SteelDrivers Band Members
Complete List Of The SteelDrivers Albums And Songs
Complete List Of Ani DiFranco Albums And Songs
Complete List Of Ani DiFranco Albums And Discography
Outlaws Albums
Complete List Of Outlaws Albums And Discography
The Prodigy Albums
Complete List Of The Prodigy Albums And Songs
11 Classic Bands Who Returned With New Music After A Long Gap
11 Classic Bands Who Returned With New Music After A Long Gap
Complete List Of All Super Bowl Halftime Performers Since 1967
Complete List Of All Super Bowl Halftime Performers Since 1967
10 Gifts Not To Buy An Old-School Music Fan
10 Gifts Not To Buy An Old-School Music Fan
20 Worst Moments In Rock Music History
20 Worst Moments In Rock Music History
Three Dog Night 1968 Debut Album Review
Review Of Living in the Material World 50th Anniversary Reissue
Review Of Living in the Material World 50th Anniversary Reissue
10 Best Breakup Songs For Shattered Hearts
10 Best Breakup Songs For Shattered Hearts
Billy Idol Rebel Yell 40th Anniversary Vinyl Review