The article explores overlooked tragedies uncovered in Old Hollywood celebrities’ autopsy reports and death certificates, contrasting the era’s glamorous image with its darker realities. It begins by referencing behavioral science insights on nostalgia: people tend to romanticize the past by downplaying its flaws, such as enduring systemic issues like gender inequality and abusive workplace practices. This context frames the examination of six influential figures whose deaths revealed personal and professional hardships. John Wayne’s death in 1979 from cancer and respiratory failure has been retrospectively linked to his time filming *The Conqueror* (1956) in Utah, downwind from U.S. nuclear tests. By 1980, 91 of 220 cast and crew members had developed cancer, with 46 deaths recorded. Experts suggest radiation exposure from nearby atomic bomb tests likely contributed to these illnesses. Errol Flynn, known for swashbuckling roles, died in 1959 at 50. His autopsy revealed severe health deterioration from chronic alcoholism, including cirrhosis and a fatty liver, alongside heart issues. His blood alcohol level was 0.25% at death, indicative of extreme tolerance. The actor’s decline followed legal scandals and professional downfall. Carole Lombard, a top 1930s star, died at 33 in a 1942 plane crash while returning from a World War II bond-selling tour. Her death certificate notes severe trauma and burns. President Franklin D. Roosevelt honored her, and her husband, Clark Gable, temporarily left Hollywood to enlist in the military. Dorothy Dandridge, the first Black woman nominated for a Best Actress Academy Award, struggled with personal trauma and societal barriers. Her 1965 death at 42 was initially attributed to a bone fragment causing an embolism, but the coroner retracted this, citing errors in the autopsy. The revised cause was drug intoxication, likely involving antidepressants, though the intent (accidental or deliberate) remains unclear. Actor Sal Mineo, 37, was murdered in 1976 after a stabbing outside his home. His autopsy documented a fatal wound puncturing the heart. Suspect Lionel Williams was eventually convicted in 1978, two years after the crime, despite discrepancies in witness descriptions. Finally, Natalie Wood’s 1981 death remains controversial. Her autopsy indicated drowning, with no signs of struggle, though the case was reclassified in 2013 as “drowning and other undetermined factors.” She vanished from a yacht trip with husband Robert Wagner and co-star Christopher Walken, whose silence intensified public speculation. The article underscores how these accounts expose the vulnerabilities of iconic figures, contrasting Old Hollywood’s curated glamour with systemic exploitation, health risks, and personal crises. While often mythologized, the era’s stars frequently endured toxic work environments, substance abuse, legal battles, and premature deaths, challenging idealized perceptions of the past.