Music legend Frank Sinatra, affectionately known as the Chairman of the Board, was one of the greatest entertainers to emerge from the 20th century. He was also one of the most powerful people in the entertainment industry at the height of his fame. He even helped support President John F. Kennedy's presidential campaign.

While there are certainly controversies surrounding Sinatra's personal life and the entertainer was even arrested, perhaps one of Sinatra's greatest accomplishments was using his influence to fight against racial discrimination.