6. Jill- Jack And Jill
In truth, I don't think any of the poor unfortunate souls who had to sit through this hot mess of a film would begrudge me picking anyone from the roster of dislikeable characters that featured in it, but it seems most fitting to hone in on the character around which this entire misguided concept was built.
Jill, played by Adam Sandler is loud, obnoxious, needy and, most offensive of all, deeply unfunny in every conceivable way. A character with any of these other traits in a comedy movie needs to carry some sense of comic relief to get away with these obvious flaws, but Jill is such a fall-flat on your face attempt at comedy that she comes across as completely and utterly unbearable.
The film is largely derided as one of the worst movies ever made, rightfully so, and a huge part of that unwanted burden sits squarely on Jill's broad shoulders. Jack and Jill is the lowest point in the career of a man who's made low points something of a speciality lately and Jill is the epitome of that struggle. A truly and rightfully reviled character.