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.

Question: what else did he do?
Self-contained rewrite: what else did Gus Van Sant do besides Idaho and Drugstore Cowboy?