I love Late night and can't wait to get Showtime, since to me they add to each other. Even though I want to have a ranch and other things, Bridgeport is my favorite town (waiting to see Showtime). I like the feel of a big city and I like the night life. Personally, i have had my sim in many careers in Brdigeport, and it doesn't matter, the career. What matters is the celebrity status. A 5 star celeb artist outweighs a 3 star actor.
So, you need charisma skills and guitar (everyone watches or plays guitar) to get to know people. throw lots of parties (gett the LTR "legendary host") and your in the game.