I've had a fascination with worsts for long enough for my oldest friend to know that a book on this aspect (of album covers) would be a good present.
It made me wonder. When I was first mulling over the idea of worsts for the last entry, I was searching for worsts. Worst food, worst animal. It made me realise how many approaches one can take to selecting the worst. The foods seemed to be bad because the old photos made it all look garish, and it was dangerously fattening. But apart from that..
And the animals were badly designed more than anything. They weren't the kind that bored into some part of your anatomy and caused you grief but freaks of nature, if you will.
In some corners of the animal kingdom this is seen as objectivity. After all, in the food chain we all have our predators and our prey. A well designed eagle should pip an awkward elk whatever the cuteness ratio of the creature it hunts.
I suppose what I see entertaining in 'worst of's is the humour of really bad, but earnest, attempts. To this end, it's probably more fruitful concentrating on things that aren't severe to start with.
Black humour has only carried me a certain way and I probably prefer a witty riposte. But the best worsts (!) are good for a laugh.