Billie Holiday faced numerous challenges throughout her musical career, notably her experiences with racism and personal trauma. Growing up in a disadvantaged environment, she struggled against systemic inequalities, which deeply influenced her music. Holiday dealt with turbulent relationships and battles with addiction, which affected her health and professional stability. These hardships enriched her emotional expression, leading to powerful performances that transcended mere entertainment. Her iconic song “Strange Fruit” poignantly addressed lynching and racial violence, cementing her place as an influential voice against oppression, showcasing her resilience and artistry amidst life's adversities.