Tina Fey + Alec Baldwin
When Tina Fey (aka the woman every other woman wants to be when she grows up), was creating '30 Rock,' she wrote the character of totally uncensored network executive Jack Donaghy with Alec Baldwin in mind. She never thought he'd actually accept the role, but was thrilled when he did.
We can't imagine anyone else playing the part, but he's certainly been a bit of a PR nightmare for Fey. Between leaving his young daughter profane-ridden voicemails, his very public run-ins with the paparazzi, and a love of 'Words With Friends' that got him punted off a plane, he'd better be glad he's really good at his job.