The "Fortune 500"  is a list of the 500 largest companies in the United States as compiled by Fortune magazine. Only 20 black executives have ever made it to the Chairman or CEO position of a "Fortune 500" listed company. Of these 20 executives, there are currently 4 active CEO's, representing less than 1% of the Fortune 500 top leadership.

In 1987, Dr. Clifton R. Wharton, Jr. became Chairman and CEO of TIAA-CREF — distinguishing him as the first black CEO of a Fortune 500 company. 

Franklin Raines became the second black person to lead a "Fortune 500" company, when he became CEO of Fannie Mae in 1999. 

Only four Black Women have ever led a Fortune 500 company. On July 1, 2009, Ursula Burns became the first black woman to head a Fortune 500 company. Ms. Burns stepped down as the CEO of Xerox in late 2016, following the completion of the separation of Xerox into two independent, publicly-traded companies. She served as chairman of the board of the post-separation Document Technology company from 2010 to 2017.

Mary A. Winston was the second Black Woman to lead a Fortune 500 company. She served as the interim CEO of Bed Bath & Beyond between May and November 2019.

Walgreens Boots Alliance, Inc. (Nasdaq: WBA) announced on January 26, 2021 the appointment of Rosalind (Roz) Brewer as the company’s Chief Executive Officer, effective on March 15, 2021. Ms. Brewer will become the third female black American to lead a Fortune 500 company.

Thasunda Brown Duckett will become the fourth Black Woman to head a "Fortune 500" company, on effective May 1, 2021, when she succeeds Roger Ferguson, who announced his retirement from TIAA in November 2020, after a 13-year run as CEO.

Black executive representation in the C-suite of America's largest companies has been on the decline. Kenneth C. Frazier is currently Executive Chairman of Merck’s board of directors, a role he began in July 2021, following his retirement from a decade-long tenure as Merck’s President and Chief Executive Officer. Marvin Ellison, who served as chairman and CEO of J.C. Penney for nearly three years and helped to revive the struggling department store chain, left the company in May 2018, to become head of Lowe’s. Kenneth Chenault stepped down as Chairman and Chief Executive Officer of American Express at the end of January 2018. He was the fourth black CEOs to have retired over the last three years. Ursula Burns left her post as head of Xerox in 2016 when the company split in two, and Rodney O'Neal retired from his role as CEO and president of Delphi in 2015. Don Thompson retired as CEO of McDonald's in 2015, as well.

There are currently no black majority owned company in the Fortune 500 rankings.

_{Updated: 2021/02/26.}