1. Daniel Cleaver – ‘Bridget Jones’ Diary’ and ‘Bridget Jones: The Edge of Reason’
A sexual harassment case on two legs, Bridget Jones’s nightmarish dream man Daniel Cleaver cuts Grant’s foppish charm with a tang of early noughties toxicity. He’s the slick publishing executive who two-times Bridge and who uses words like ‘shagathon’ without a hint of embarrassment. Following the run of smash-hit rom-coms that made him a star, the character was an early hint that Grant’s next act would see him subvert his winningly self-mocking persona and turn to the dark side. Perhaps deservedly, Cleaver is killed off before he can sin again in Bridget Jones’s Baby.