Conversation so far:
what was a movie Gus Van Sant made in this style?
Drugstore Cowboy's exploration of the lives of those living on society's outer fringes, as well as its Portland setting, were mirrored in Van Sant's next effort.
when was it released?
acclaimed My Own Private Idaho (1991).
did he make any other films?
license to make Idaho (a film he had originally pitched but was knocked back several times as the script was deemed 'too risky' by studios).
was Idaho a sucess?
The film won him an Independent Spirit Award for his screenplay (he had won the same award for his Drugstore Cowboy screenplay), as well as greater prestige.
what else did he do?
Van Sant's next film, a 1993 adaptation of Tom Robbins' Even Cowgirls Get the Blues.
did he win any awards?
The film won him an Independent Spirit Award for his screenplay.
was that his only award?
The film also gained River Phoenix best actor honors at the Venice Film Festival among others.

Question: what was his most famous movie?
Self-contained rewrite: what was Gus Van Sant's most famous movie?