Actor and filmmaker Robert Downey Sr. has passed away in his sleep at the age of 85. He was best known for his comedies and for his later appearances in films such as Boogie Nights andMagnolia, as well as for being the father of acclaimed actor Robert Downey Jr.

Robert Downey Sr. first emerged as an artistic force in the 1960s with independent films like Chafed Elbows and Putney Swope, though at the time his work remained deliberately obscure (as was the norm with countercultural filmmakers). He continued to write and direct similar underground movies throughout the following decades, though he also expanded into more conventional work, such as directing episodes of the 1985 remake of The Twilight Zone.

Soon after the release of Putney Swope, Downey began to gain clout as an actor, with small roles in movies like To Live and Die in L.A. and You've Got to Walk It Like You Talk It or You'll Lose That Beat. At one point, he even appeared opposite his son Robert (born in 1965) in the 1994 film Hail Caesar. Later in life, he mostly retired from directing, though he continued to act with zest. It was during this time that he struck up a friendship with auteur Paul Thomas Anderson, who was a long-time admirer of Downey's work.

Soon after his final film appearance in 2011's Tower Heist, Downey contracted Parkinson's disease, which he would struggle with for over half a decade. Downey is survived by his wife Rosemary Rogers and his children, Robert Downey Jr. and Allyson Downey.