I have to admit to one of my pet sub-sub-genring ways; I have a deep affinity for songs and albums made by pre-British-invasion-era artists trying to remain with it in the mid to late 60s, or as I call them PBIEATTRWIITMTL6Ts (which is why I don't talk about them very often).
If you've been here for some time you already know I consider DION AND THE WANDERERS to be one of the best thing that happened to humanity.
But there are many other examples of great songs made by artists who had commercially peaked before the Beatles, and whose attempts at remaining current are both convincing and cute: MEL TORME, THE FOUR SEASONS (that whole album is a golden example of what I'm talking about), PEGGY LEE, ROY ORBISON, DEL SHANNON of course, and that's just what's on top of my head right now.
And one day I found possibly the best album of that whole sub-sub-genre: BOBBY DARIN BORN WALDEN ROBERT CASSOTTO, a 1968 oddity full of references to LSD and social changes, written, arranged, produced, designed, photographed and released on hiw own label, by the man I mostly knew for bringing Kurt Weill and Charles Trénet into the American charts. Just dig these: