One of the signature independent directors of the 1960s and ’70s has died. Robert Downey Sr. passed away on Wednesday at his home in New York City. He was 85 years old. His death was confirmed by the New York Daily News; his wife, Rosemary Rogers, told the Daily News that Downey died in his sleep after a long battle with Parkinson’s disease.

Downey first began making underground films in the 1960s. His works as director include Greaser’s PalacePound, and Up the Academy, the only movie to date directly inspired by Mad Magazine. His most famous movie remains Putney Swope, a blistering satire of the advertising industry and race in America.

Downey’s work influenced many modern filmmakers, including Paul Thomas Anderson, who loved Downey’s movies so much he named Don Cheadle’s character in Boogie Nights “Buck Swope“ and cast Downey in the role of Burt, the recording studio owner who refuses to turn over Dirk’s tapes until they pay him:

Downey’s other acting credits included MagnoliaTo Live and Die in L.A., and Tower Heist. Here is a video from the Criterion Collection of Downey Sr. and Paul Thomas Anderson in conversation:

Downey Sr. was also, of course, the father of actor Robert Downey Jr. Long before he became Iron Man — long before he even became a cast member on Saturday Night Live — Robert Downey Jr. made appearances in his father’s films. In fact, Downey Jr.’s very first screen role came at the age of 5 in Downey Sr.’s Pound.

While most young people are more familiar with Robert Downey Jr., Robert Downey Sr. was an extremely accomplished filmmaker in his own right. If you’ve never seen Putney Swope, you need to rectify that. It’s currently streaming on several different sites, including Tubi.

UPDATE: Here’s Robert Downey Jr.’s tribute to his father: “He was a true maverick filmmaker.”

The Most Influential Movies of the 21st Century

More From ScreenCrush