Jessica Simpson – $2,000

Jessica Simpson is known not just in the music industry but also in Hollywood as well. Her breakthrough was when she was signed by Tommy Mottola, who wanted the young singer to focus on having a wholesome image to counter that of Britney Spears. Simpson’s debut single, I Wanna Love You Forever, reached the number three spot in the Billboard Hot 100. She also starred in a reality TV show with her then-husband, Nick Lachey.

Simpson was also one of the celebrities who used her investment money to get cosmetic surgery, starting with her lips. Later on, she got a tummy tuck, but it put her in the hospital after getting an infection. Simpson was quite frank about her experience in her autobiography. Hopefully, she has since bounced back from her ordeal as the singer turned actress is still a gorgeous beauty.