5. E. Edward Grey
James Spader has always had a penchant for playing devious characters, from his breakthrough role as Steff in Pretty In Pink to the most recent Red in The Blacklist. Although, for our purposes, Cheryl need not look any further than the soft spoken, unflinching and very dominant Edward Grey, Esq from 2002's Secretary. It's the obvious choice if you're really familiar with Spader's body of work, but it's also the best. ISIS (or rather, what's left of it) might seem more lucrative, but working with Mr. Grey would certainly have it's perks. Considering her already ample experience, she wouldn't need any training. Every time she makes a mistake she'd be rewarded with copious amounts of verbal criticism and a spanking. Cheryl would be allowed, no, encouraged to wear restraints in the office. There's nothing steamier than a highly unethical and aggressive sexual relationship in the workplace. It doesn't even need to stop there. All of those late night calls from Mr. Grey would be really considerate. I'm sure Cheryl would find it super romantic to have someone stalking her for a change, too. They could even make a game out of it and stalk each other!