The U.S. Supreme Court did not lift the nationwide ban on interracial marriage until June 12, 1967. But years before the high court’s pivotal decision, dozens of celebrities in and out of Hollywood partnered with couples of different racial backgrounds. This list includes 12 actors, athletes, authors, singers and socialites collectively who crossed the color line for love long before interracial marriage became widely accepted.

During a time in which black men could be lynched for even looking at a white woman the “wrong way,” boxer Jack Jackson started romantic relationships with several white women. After romancing a series of prostitutes who were black and white alike, Johnson married New York socialite Etta Terry Duryea in Pittsburgh in January 1911. The couple tried to keep their marriage a secret, but a year after the interracial couple tied the knot word of their union spread back to Brooklyn. The abusive nature of her relationship with Johnson, the death of her father, disapproval of her interracial marriage and a history of depression all likely contributed to Duryea’s decision to kill herself in September 1912.

Just weeks after Duryea’s suicide, Johnson started a romance with 18-year-old white prostitute Lucille Cameron. Due to outrage over his relationship, Johnson was arrested for breaking the Mann Act, which made it illegal to travel across state lines “for the purpose of prostitution or debauchery, or for any other immoral purpose,” according to PBS.

When broadly applied, the Mann Act could be used to outlaw all premarital and extramarital sexual relationships that involved interstate travel, PBS reported. On Dec. 4, 1912, Johnson married Cameron. The following year he was convicted of violating the Mann Act for his relationship with Cameron. The couple lived abroad for several years, with the boxer spending nine days in jail related to his Mann Act conviction.

Cameron filed for divorce from Johnson four years later because the known womanizer had been unfaithful to her.

In August 1925, Johnson

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