The decade between 1958 and 1968 was, by Nicholson’s own accounting, a decade of sustained effort in the face of limited breakthrough. He accumulated credits — small roles, B-movies, television appearances — and he also began writing screenplays, work that reflected his interest in how films were constructed rather than just how they were performed. By the late 1960s he had roughly twenty film credits and had written at least two produced screenplays, but he was not a star. He was a working professional in a crowded field, someone whose talent was recognized within a specific part of the industry without yet reaching the mass audience.
The break, when it came, arrived sideways.
Easy Rider, the 1969 Dennis Hopper-Peter Fonda motorcycle road movie that became one of the defining films of its era, was not originally planned to include Jack Nicholson. The part he eventually played — a Southern alcoholic lawyer named George Hanson, a character who joins the bikers’ journey for a portion of the film — was written for Rip Torn. When Torn departed the production under circumstances that have been described differently by different participants, Nicholson stepped in.
His performance in Easy Rider earned him his first Academy Award nomination for Best Supporting Actor. It was 1969, he was thirty-two years old, and he had been working in Hollywood for eleven years. The nomination changed the terms of how the industry saw him. He was no longer a working journeyman with good reviews in B-movies. He was an Oscar-nominated actor whose face carried something that other faces did not.