Jessica Simpson: 16-Year-Old Drop-Out
If Tommy Mottola wants to make you a star, you drop everything — including high school — to go for it. Two-time Homecoming Queen nominee Jessica Simpson was made just such an offer and ended up dropping out of JJ Pearce High School at age 16, when she was signed to Columbia Records. (She later earned a GED.) Given that she’s now worth over $100 milion, it looks like Jessica made the right decision.