Harry Belafonte set his own barrier-breaking records; his 1956 album “Calypso” introduced the United States to the traditional Caribbean musical genre and was the first full-length album to sell over a million copies, per Biography. He was also the first Black performer to win an Emmy award, which he did in 1959 for “Revlon Revue: Tonight with Belafonte.”
In August 1964, Belafonte and Poitier made a daring and heroic trip to Greenwood, Mississippi, as recounted by Andrew Cohen for the Ottawa Citizen. That historic summer, known as Freedom Summer, saw a bevy of Northern college students traveling to the Southern United States in order to register Black citizens to vote. Jim Forman contacted Belafonte to ask for help, and Belafonte quickly raised $70,000 in funds (the modern equivalent of $600,000) and decided to hand-deliver it himself. According to Ottawa Citizen, he asked Poitier to accompany him on the mission, reportedly telling his friend that it would “be harder for them to knock off two Black stars than one. Strength in numbers, man.” When they landed in Mississippi, a car chase ensued, with members of the KKK attempting to goad them into speeding. The was an attempt to force the driver into a speed trap, leading to the passengers getting arrested, freed, and turned over to the KKK, which had happened in the past to civil rights activists.