This song marks a minor turning point in Popular: it’s the very last which I had absolutely no memory of ever hearing when I started the project. Plenty of later ones are forgettable – even more forgettable than poor Jim – but this is my final “here be dragons”.
As dragons go, this is a somewhat puny specimen; its tail is drooping and it suffers from scale rot. Can it still breathe fire? Only on the howled “IY-YI-YI-YI” hook, which I’d say was the only reason anyone bought this except it takes its own sweet time getting there. And once it’s past the energy level quickly drops again: “I Should Have Known Better” wants to be a big-striding alpha power ballad but doesn’t quite have the gumption, which perhaps explains its lack of afterlife.
The rest of the song is sturdy, chest-beating guilt pop which never quite escapes the stocky shadow of Phil Collins. But while Collins at his ugly best captures the rage and frustration lurking behind male regret, Diamond is just a bit of a sad sack, appealing though his chewy Scots vowels are. You clap him sympathetically on the shoulders with one hand while sneakily checking your watch on the other.