I don't know how obscure these films are in the grand scheme because I don't know how well they did when they were released, but I love Little Big League, Baby's Day Out, First Kid, and Dunston Checks In which were all released in the mid 1990's.
Would only be obscure to some people:
"After Hours"
And only funny to people who can relate to big city nights where you feel you might never get home. *L*