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. These songs aren’t simply about regret; they deal with admitting mistakes, living with them, learning from them, and sometimes just moving on.

# 10 – $29.00 – Tom Waits

“$29.00” appears on Tom Waits’ 1978 album Blue Valentine, where its dark story follows a young woman leaving home only to find herself in an even more dangerous situation. Recorded at Filmways/Heider Recording with producer Bones Howe, the song is built around the kind of street-level storytelling that can recall Bob Dylan, but Waits gives it his own grim, jazz-and-blues-soaked atmosphere. The title’s “twenty-nine dollars and an alligator purse” becomes part of the song’s picture of a bad decision leading somewhere worse.

Read More: Our 10 Favorite Tom Waits Albums

# 9 – Girl Afraid – The Smiths

“Girl Afraid” was released in 1984 as a B-side to “Heaven Knows I’m Miserable Now” and later appeared on Hatful of Hollow. Written by Morrissey and Johnny Marr and produced by John Porter, the song was recorded at Fallout Shelter in London. Its anxious back-and-forth between two people who completely misunderstand each other makes it a natural fit for a list about mistakes.

Read More: Our 10 Favorite Smiths Songs

# 8 – The Wrong Thing to Do – Mudcrutch

“The Wrong Thing to Do” comes from Mudcrutch’s self-titled 2008 debut album, recorded after Tom Petty reunited the band more than three decades after its original breakup. Petty, Mike Campbell, Benmont Tench, Tom Leadon, and Randall Marsh returned to the rootsy rock and country sound of their early years, with Petty, Campbell, and Ryan Ulyate producing the album. The title alone makes the song an easy choice here, but its loose, direct feel also keeps it from sounding like an overthought lesson in regret.

# 7 – Biggest Mistake – The Rolling Stones

“Biggest Mistake” appeared on The Rolling Stones’ 2005 album A Bigger Bang and was released as the album’s third single in 2006, reaching No. 51 on the UK Singles Chart. Written by Mick Jagger and Keith Richards, the acoustic-driven song looks back at a failed relationship from the point of view of someone who knows he was responsible for losing it. It is one of the most literal matches on this list.

Read More: Top 75 Rolling Stones Songs

# 6 – It’s a Mistake – Men At Work

“It’s a Mistake” was released from Men At Work’s 1983 album Cargo. Written by Colin Hay and produced by Peter McIan, the song takes the idea of a mistake far beyond personal relationships, using Cold War fears and the possibility of military miscalculation as its subject. It became the band’s fourth and final U.S. Top 10 hit, reaching No. 6 on the Billboard Hot 100.

Read More: Top 10 Men At Work Songs

# 5 – Love Mistake – Heart

“Love Mistake” comes from Heart’s seventh studio album, Passionworks, released in 1983. Produced by Keith Olsen, the album introduced drummer Denny Carmassi and bassist Mark Andes and reached No. 39 on the Billboard 200. “Love Mistake” deals with romantic disappointment without overcomplicating the point. 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 whether to pick Randy Newman’s version or Three Dog Night’s classic, but 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 Newman, Three Dog Night’s recording reached No. 1 on the Billboard Hot 100 in 1970, with a bewildered narrator realizing that attending this wild party may have been a mistake. 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)” was one of the new songs included on Billy Joel’s Greatest Hits – Volume I & Volume II in 1985 and became a U.S. Top 10 hit. Joel wrote the song as an encouraging message for young people dealing with depression and thoughts of suicide, reminding listeners that mistakes and setbacks are part of being human. That message makes it one of the most direct songs on this list about accepting failure and continuing forward.

# 2 – My Favorite Mistake – Sheryl Crow

“My Favorite Mistake” was released in 1998 as the lead single from Sheryl Crow’s third studio album, The Globe Sessions. Written by Crow and Jeff Trott, the song reached No. 20 on the Billboard Hot 100 and earned a Grammy nomination for Best Female Pop Vocal Performance. Crow frames a painful relationship as a mistake she can recognize without pretending it meant nothing, which is exactly why the song works so well near the top of this list.

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

“Won’t Get Fooled Again” closes The Who’s 1971 album Who’s Next and was written by Pete Townshend. Rather than focusing on one personal mistake, the song looks at the repeated mistakes of political and social revolutions, where promises of change can lead right back to the same old power structure. That hard-earned refusal to fall for the same illusion twice makes it a perfect number one for this list.