Bruno Ganz, whose best-known roles were portraying the extremes of an angel and Adolph Hitler, died in Zurich at age 77 on Friday. His cause of death was colon cancer, according to representatives.

His memorable portrayal of German dictator Adolph Hitler in 2004’s Downfall was considered Ganz’s biggest role. But his appearance as an angel in the 1987 Wim Wenders film Wings of Desire also drew accolades. He later reprised that role in the 1993 follow, Faraway, So Close!

Among his other critically hailed roles included appearances in Stephen Daldry’s Oscar-nominated The Reader (2008), Werner Herzog’s Nosferatu, the Jonathan Demme remake of The Manchurian Candidate and Franklin J. Schaffner’s The Boys from Brazil.  

But it was the role of Hitler that truly made Ganz. Some criticized him for humanizing the brutal dictator, but Ganz’s portrayal later became popular in the social media age, as clever meme creators gave people the opportunity to change the dialog of Ganz’s raving.

Beyond films, Ganz performed on the stage in Harold Pinter’s “The Homecoming” and Goethe’s “Faust.”

Ganz’s most recent film appearance was in Lars von Trier’s The House That Jack Built, a Cannes premiere last year.