24. Philip Seymour Hoffman
This tintype photograph, taken at the 2014 Sundance Film Festival in Utah, is one of the last known public appearances of Oscar-winning actor Philip Seymour Hoffman. The actor, who had been struggling with addiction for 23 years, was found dead in his apartment after a heroin overdose two weeks later.
23. Bob Marley
Reggae icon Bob Marley is seen here at 36 years old, weighing only 77 pounds after battling a rare form of skin cancer for four years. He’s pictured on his way to Jamaica after eight months of unsuccessful treatment in Pennsylvania, though he never made it home. His last words to his son Ziggy were “Money can’t buy life.”
22. The Challenger Crew
21. James Gandolfini
James Gandolfini, who starred in The Sopranos for nine years, died in Italy in 2013. He was on a vacation with his family at the time and suffered a heart attack at age 51.
“He touched so many of us over the years with his humor, his warmth, and his humility,” said a spokesperson with HBO.
20. Marilyn Monroe
This photo shows Hollywood icon Marilyn Monroe in Nevada with musician Buddy Greco, just days before she was found dead in her home after an overdose of prescription barbiturates. She was only 36 years old in August 1962, and her untimely death is still surrounded by conspiracy theories to this day.