Jessica Simpson — $1 Billion Fashion Brand

Jessica Simpson's fashion brand reached $1 billion in annual retail sales in 2014 — the most successful celebrity fashion venture ever, and 40% larger than Sean John's peak revenue. Her pop career peaked with "I Wanna Love You Forever" and a reality show where she asked if Chicken of the Sea was chicken. While internet mockers laughed, she built a 30-category lifestyle brand across 1,000+ stores. Her net worth is $200 million — triple the average musician-made-from-music fortune. The "dumb blonde" was the shrewdest.