10 Best Rock Songs About Mistakes

Feature Photo: Raph_PH, CC BY 2.0 <https://creativecommons.org/licenses/by/2.0>, via Wikimedia Commons

Now, this is going to be fun. This article focuses on one of life’s unavoidable truths: making mistakes. While many songs reflect on regret or the idea of not looking back, this list is different. It’s not about dwelling on what went wrong or wishing things had turned out differently. Instead, this is an exploration of songs that embrace the reality of mistakes—whether it’s accepting personal missteps, acknowledging others’ errors, or admitting that sometimes, mistakes just happen. The essence here isn’t necessarily regret or reflection, but a simple admission: “Yes, it was a mistake.” And once that’s recognized, it’s about moving forward.

# 10 – $29.00 – Tom Waits

“$29.00” by Tom Waits opens Blue Valentine and sets a dark, cinematic tone that encapsulates the theme of mistakes, fitting perfectly as the first entry on a list of the 10 Best Rock Songs About Mistakes. Released on September 5, 1978, Blue Valentine was recorded over six sessions from July to August of that year with producer Bones Howe at Filmways/Heider Recording in Hollywood, California. Known for its brooding, film-noir atmosphere, the album is a gritty reflection of urban life, and “$29.00” is one of its most harrowing tales. The song presents a vivid narrative about a young girl who leaves home, only to encounter danger and deception, ultimately realizing that the escape she longed for comes at a greater price than expected.

The lyrical imagery of “twenty-nine dollars and an alligator purse” symbolizes the meager possessions and precarious situation of the protagonist, reinforcing the sense of entrapment. As the story progresses, she realizes that running away from one problem has only led her into another. The song’s storytelling evokes a feel similar to Bob Dylan’s Highway 61 Revisited or Bruce Springsteen’s early narratives, blending street-level storytelling with haunting metaphors. However, Waits’ gravelly, world-weary delivery and penchant for jazz-inflected blues sets his work apart, creating a unique voice in rock and roll’s exploration of life’s darkest corners.

Read More: Our 10 Favorite Tom Waits Albums

# 9 – Girl Afraid – The Smiths

“Girl Afraid” by The Smiths is a quintessential example of the band’s ability to craft emotionally complex narratives within the framework of jangly, melodic indie rock. Released in 1984 as the B-side to the hit single “Heaven Knows I’m Miserable Now,” the song was later included on the compilation album Hatful of Hollow. Written by Morrissey and Johnny Marr, the track features the iconic interplay between Marr’s intricate guitar work and Morrissey’s melancholic lyricism. Recorded during The Smiths’ prolific early years, the song showcases the band’s evolving sound as well as their adeptness at blending sharp, introspective lyrics with vibrant musical arrangements. “Girl Afraid” was recorded at the BBC’s Maida Vale Studios in London with producer John Porter, capturing the raw, yet polished sound that defined The Smiths’ early releases.

# 8 – The Wrong Thing to Do – Mudcrutch

“The Wrong Thing to Do” by Mudcrutch is a gritty, Southern-tinged rock track from the band’s self-titled debut studio album, released on April 29, 2008. Mudcrutch, initially formed in 1970, was a precursor to Tom Petty and the Heartbreakers, featuring the late Tom Petty and band members Mike Campbell and Benmont Tench. After disbanding in 1975 without releasing a full-length album, Mudcrutch reunited over 30 years later to record their debut. Produced by Tom Petty and Mike Campbell, the album was recorded over a two-week period in August 2007, marking a return to their early rock and country influences. The song, alongside the album, showcases the raw, organic sound of a band rediscovering its roots, merging rock with country and Americana elements.

# 7 – Biggest Mistake – The Rolling Stones

“Biggest Mistake” by The Rolling Stones is a standout track from their 2005 album A Bigger Bang, serving as a poignant reflection on regret and lost love. Released on August 21, 2006, as the album’s third single, the song reached number fifty-one on the UK Singles Chart. With lyrics penned by Mick Jagger and Keith Richards, the song explores the aftermath of a failed relationship. There’s a strong suggestion that the song reflects Jagger’s breakup with supermodel Jerry Hall, although this has never been officially confirmed. The song’s acoustic guitar-driven melody complements its introspective lyrics, offering a pop sensibility while keeping in line with the Stones’ trademark sound.

Read More: Top 75 Rolling Stones Songs

# 6 – It’s A Mistake – Men At Work

“It’s a Mistake” by Men at Work, released as the third single from their 1983 album Cargo, takes on a much broader and more political context than many other songs on this list. Written by lead singer Colin Hay and produced by Peter McIan, the track reflects the fears and uncertainties of the Cold War era, with lyrics that highlight the potential consequences of military miscalculations. The song, released in June 1983, became one of the band’s last major hits, peaking at number six on the Billboard Hot 100 and serving as a testament to Men at Work’s ability to mix pop sensibilities with serious thematic content.

Read More: Top 10 Men At Work Songs

https://www.youtube.com/watch?v=I0AxrOUJ62E

# 5 – Love Mistake – Heart

“Love Mistake” from Passionworks, Heart’s seventh studio album, captures the band’s shift from their hard rock roots to a more mainstream rock sound, reflective of the evolving musical landscape of the early 1980s. Released in August 1983 by Epic Records, Passionworks saw Heart adopting a more polished, radio-friendly approach, departing from their earlier, folk-inspired hard rock sound. This album also marked a significant personnel change with Denny Carmassi on drums and Mark Andes on bass, replacing longtime members Mike Derosier and Steve Fossen. Produced by Keith Olsen, Passionworks failed to hit the chart-topping success of Heart’s earlier albums, peaking at number 39 on the Billboard 200. However, “Love Mistake” remains one of the standout tracks, delving into themes of heartbreak and emotional vulnerability. I just love Heart, and this is one of their most underrated albums.

# 4 – Mama Told Me Not To Come- Three Dog Night

Yes, of course, we had to have this one on the list. The real decision was who to pick, Randy Newman’s original version or, of course, Three Dog Night’s classic. In the end, since we are such big Three Dog Night fans here at the site, and I’ve been listening to that band since I was a kid and have every single one of their records, I had to go with their version. Written by Randy Newman, the song became one of Three Dog Night’s most recognizable hits, reaching number one on the Billboard Hot 100. It is a humorous yet cautionary tale of a young man’s bewildering experience at a wild party, where the overwhelming chaos leads him to regret attending. I always wish I had been at that party too.

Read More: Top 10 Three Dog Night Deep Tracks

# 3 – You’re Only Human (Second Wind) – Billy Joel

“You’re Only Human (Second Wind)” by Billy Joel is an uplifting anthem about resilience and perseverance in the face of personal mistakes and setbacks. Released in 1985 as part of Greatest Hits – Volume I & Volume II, the song reached number nine on the Billboard Hot 100 and was praised for its message of hope, encouraging listeners to keep pushing forward despite failures.

Billy Joel wrote the song after being approached by his label to create something addressing teenage depression and suicide prevention. He drew on his own experiences of struggle to remind listeners that mistakes and tough times are a part of life, but they don’t define a person. The lyrics include empowering lines like, “You’re only human, you’re allowed to make your share of mistakes,” and “Don’t forget your second wind,” urging people to not give up when life gets hard. The term “second wind” refers to the boost of energy or renewed determination that comes after a period of fatigue, highlighting the theme of bouncing back from adversity.

# 2 – My Favorite Mistake – Sheryl Crow

“My Favorite Mistake” by Sheryl Crow is a reflective and bittersweet song about a complicated relationship filled with regret and mixed emotions. Released in 1998 as the lead single from her third studio album The Globe Sessions, the song reached number 20 on the Billboard Hot 100 and became one of Crow’s most enduring hits. It was also nominated for a Grammy Award for Best Female Pop Vocal Performance, solidifying its place in Crow’s catalog of powerful and emotionally resonant songs.

Lyrically, “My Favorite Mistake” captures the feelings of betrayal and heartache, but also hints at a deep, lingering affection for someone who has wronged the narrator. Crow sings about the complexity of loving someone who continues to hurt her, with lines like, “Did you know when you go, it’s the perfect ending to the bad day I was just beginning?” Despite the pain caused by the relationship, the protagonist refers to this person as her “favorite mistake,” suggesting that while the relationship was flawed, it still held significant meaning for her.

# 1 – Won’t Get Fooled Again – The Who

“Won’t Get Fooled Again” by The Who is an iconic rock anthem from the band’s 1971 album Who’s Next, and it serves as a powerful closing song for this list of the 10 Best Rock Songs About Mistakes. Written by Pete Townshend, the track is a scathing commentary on the cyclical nature of political and social revolution, where the promise of change often leads to disappointment and a return to the status quo. The song captures the essence of learning from mistakes, both personal and collective, and resolving not to fall for the same illusions again.

As the closing song on this list, “Won’t Get Fooled Again” is the perfect anthem of defiance and wisdom earned through experience, making it a fitting finale to an exploration of songs about mistakes.