Bonnie and Clyde, 1967. starring Warren Beatty and Faye Dunaway, with Michael J. Pollard, Gene Hackman, and Estelle Parsons.
The film isnt historically overly accurate but you get the gist... It was controversial at the time of release because of its apparent glorification of murderers, and for its level of graphic violence, which was unprecedented at the time.
It did open up cinema tho. It was nominated for 9 academy awards and won 2.