Stacey Y is looking for a career that will allow her to have sex appeal. She doesn't want to work hard, and values continued learning. She enjoys Arts and Writing, and is good at managing people.
Lucille (Sin City) Probation and parole officers look after people on probation or parole. In Sin City, Lucille is Marv's parole officer and friend (this doesn't happen often, I assure you), and everything goes swimmingly until some crazy guy eats her hand and she gets shot... bummer.
Miss Baggoli (Confessions of a Teenage Drama Queen) People don't just intrinsically know how to act or do stagecraft. This the job of the drama teacher. It isn't easy acting up with kids all day, but Baggoli loves it way too much.
Cruise Director Julie McCoy (The Love Boat) If the booze should ever run out on a ship, mutiny would be inevitable. Hence the presence of the cruise director. Julie McCoy was the cruise director of the worst cruise line imaginable, the Love Boat, and I blame the overall crappiness of that show on her.
Chef (South Park) Cooks are great! They make the food that you can't make yourself. Chef proves you can be a sexy cook, and that you can say terrible, terrible things to children without repercussions.
Erin Brockovich (Erin Brockovich) A paralegal works administratively under the direct supervision of a lawyer. Erin Brokovich (played by that misery, what's-her-face) is a paralegal, and it's due to her hard work that the movie ends happily ever after.