Jim Diamond – “I Should Have Known Better”:
A Heartbreak Anthem with No Safety Net
Released in October 1984 as the lead single from his debut solo album Double Crossed, “I Should Have Known Better” marked Jim Diamond’s return to the spotlight with a raw, emotionally charged ballad. Known previously as the voice behind Ph.D’s synth-pop hit “I Won’t Let You Down,” Diamond stripped away the gloss for something more vulnerable — and it resonated deeply.
A Vocalist Unleashed
Diamond’s voice was never one to hide behind production. On this track, he leans into every ounce of regret, building from a trembling whisper to a near-shout of anguish. The chorus — “And I should have known better / To lie to one as beautiful as you” — is simple, but his delivery makes it feel devastatingly personal. There’s no filter, no polish — just a man laying his heart bare.
Minimalism with Maximum Impact
While not as sparse as a piano-and-strings ballad, the arrangement is still restrained by mid-’80s standards. Produced by Diamond and Pip Williams, the track features synthesizers, guitar solos, and layered instrumentation, but everything is in service of the vocal. It’s a power ballad that avoids melodrama, opting instead for sincerity and space.
Chart Climber with a Message
The song reached No. 1 on the UK Singles Chart in December 1984, knocking Wham!’s “Freedom” from the top. In a widely admired move, Diamond publicly encouraged fans to buy Band Aid’s “Do They Know It’s Christmas?” instead of his own single, showing not just emotional depth but moral clarity.
Internationally, the song was a major hit: No. 1 in Australia, Ireland, and Portugal, No. 2 in Norway and the Netherlands, No. 3 in Switzerland and Belgium, and Top 5 in Italy and South Africa. It was later re-recorded in 1993 and again in 2005, underscoring its lasting resonance.
A Video of Isolation and Emotion
The official music video features Diamond performing in a stylized, shadowy setting — not quite minimalist, but focused entirely on his emotional delivery. There’s no storyline, no distractions — just light, shadow, and heartbreak.
A Power Ballad Without Pretension
“I Should Have Known Better” remains one of the most emotionally honest pop ballads of the 1980s. It doesn’t hide behind metaphor or production tricks. It’s all feeling, all confession — delivered by one of the most underrated voices of the decade. While Diamond never again reached the same commercial peak, he left behind a song that still speaks to anyone who’s ever regretted the one that got away.