1. London School of Economics student: Mick Jagger
2. Burlesque show performer:  Lady Gaga
3. New York City police officer: Eddie Money
4. A "Fly Girl" on "In Living Color": Jennifer Lopez
5. Student at the Royal Scottish Academy of Music and Drama: Sheena Easton
6. Dancer and choreographer for the L.A. Laker Girls: Paula Abdul
7. Telephone installer who got fired for swearing at customers: John Mellencamp
8. Translator at Miami International Airport: Gloria Estefan
9. Guitar and banjo teacher: Jerry Garcia
10. Chicken plucker: Chubby Checker
11. Computer operator - in the 70s!: Elvis Costello
12. Elementary school teacher and backup singer for Michael Jackson: Sheryl Crow
13. Back-up dancer and roadie for Digital Underground: Tupac Shakur
14. Drug dealer: 50 Cent
15. "Kids Incorporated" cast member: Fergie
16. Burger King worker in Chicago: Jennifer Hudson
17. Sales clerk in a New York City vintage clothing store: Cyndi Lauper

Bonus: Mailroom worker, weatherman, and news announcer in Utica, New York: Dick Clark