Jessica Simpson — $1 Billion Fashion Brand

Jessica Simpson's fashion empire hit $1 billion in annual retail sales in 2014 — making it the most successful celebrity fashion brand ever launched. This from a woman whose pop career peaked with "I Wanna Love You Forever" and a reality show where she asked if Chicken of the Sea was chicken. The joke was always on us: while the internet mocked her, she was quietly building a 30-category lifestyle brand spanning shoes, handbags, clothing, and fragrance across 1,000+ retail locations. Her net worth: $200 million. The "dumb blonde" was the smartest person in the room.