Definately yes because it would be
A) an awesome night
and
B) Massive Advertisement
After a celebrity "melts at the knees" when talking about our performance, it would be free advertisment about it to others which is also great for money, could totally write books, go on talks shows, etc. and make enough money to live comfortabley. Not to be too proud of my abilities, but I can say this because I have never had anyone not become broken and unable to think at some point throughout the night with me, usually with a "stop stop I need a breather to collect myself cause I cant control my body anymore" type of responce from her. So yes I can assume that I would do good.
As for who, they're are so many beautiful women that I would care more about their brain, I would want them to awesome in personality, and also for bed purposes at least a little kinky, biting as a minimum. I would definately want battle scars from the encounter. The problem is finding that out about the many celebs out there. Hmm.... maybe Stana Katic or Mila Kunis