After stints performing with Count Basie and Artie Shaw, Holiday opened the Café Society, the first non-segregated nightclub in New York City, and did the two-year residency there that shot her to fame. The surveillance of Holiday by the FBI and the BNE (Bureau of Narcotics) started not long after she began her residency there. It intensified after she began singing "Strange Fruit," a song about a lynching. Barney and Leon Josephson, who owned the club, were considered shills for the Communist Party and were later prosecuted.
Holiday's political views, as well as her drug use, made her a target for surveillance. Talking about "Strange Fruit" and "the Jim Crow–sanctioned racism that motivated her to sing it," she publicly said, "That's what made me a communist. Everybody should be a communist—not like the communists you meet at benefits and rallies, though. Not that stuff, at all. But we should all believe in treating each other as human beings. Everybody should have the chance to eat and sleep in peace." Like others in the African-American community at the time, it was the Communist Party's stance on racial equality that won her support, writes Alexander.
Bitter Crop recounts that Holiday "had smoked marijuana since she was a teenager" and that "she particularly enjoyed sneaking off from Café Society between sets to smoke a reefer while driving around the city in a taxi." It was mostly men who took her down into heroin, starting by smoking opium with her husband Jimmy Monroe, whom she married in 1941. When Truman Capote saw her perform at the time, he wrote of "my most beloved American singer—then, now, forever....Billie, an orchid in her hair, her drug-dimmed eyes shifting in the cheap lavender light, her mouth twitching out the words."