Oprah Winfrey
Net worth: $2.5 billion

Born in rural Mississippi to a poor unwed teenaged mother, and later raised in an inner city Milwaukee neighborhood, Winfrey was raped at the age of nine, and at fourteen, gave birth to a son who died in infancy. Sent to live with the man she calls her father, a barber in Tennessee, Winfrey landed a job in radio while still in high school and began co-anchoring the local evening news at the age of 19.

Her emotional ad-lib delivery eventually got her transferred to the daytime talk show arena, and after boosting a third-rated local Chicago talk show to first place, she launched her own production company and became internationally syndicated.

Winfrey became a millionaire at age 32 when her talk show went national. Because of the amount of revenue the show generated, Winfrey was in a position to negotiate ownership of the show and start her own production company. By 1994 the show’s ratings were still thriving and Winfrey negotiated a contract that earned her nine figures a year.

Considered the richest woman in entertainment

by the early 1990s, at age 41 Winfrey’s wealth crossed another milestone when with a net worth of $340 million, she replaced Bill Cosby as the only African American on the Forbes 400. Although blacks are 12% of the U.S. population, Winfrey has remained the only black person wealthy enough to rank among America’s 400 richest people nearly every year since 1995.