On September 15, America lost one of its coolest men, Harry Dean Stanton.

There’s so much we loved about Stanton, the Kentucky-born World War II veteran who discovered his love of acting in a college drama class. A notorious lone wolf on-screen and off, Stanton seemed to be everywhere all the time, appearing in more than 200 films and TV shows in his 60-year career. Yet somehow, we never got tired of him.

“Play yourself” was the advice Jack Nicholson gave Stanton when he wrote a part for him in the 1966 outlaw film Ride the Whirlwind, and that’s exactly what he did — for the rest of his career. Stanton’s naturalistic technique made him the perfect fit for all his roles, and that’s saying a lot. Here’s a look back at some of our favorites.