Medium Cool is a unique Chicago movie to say the least.

Directed by Chicagoan Haskell Wexler, Medium Cool is notable for blending fictional storytelling and documentary techniques that, astonishingly, climax right in the middle of the riots during Chicago's 1968 Democratic National Convention. 

As Roger Ebert once put it, “There are fictional characters in real situations...there are real characters in fictional situations.”

Principal shooting for Medium Cool began in Chicago on July 29, 1968. When the upheaval started in late August, the cast and crew jumped into the chaos. They tried to blend in with the crowd as much as possible so others would not notice they were filming a movie.

In the center of this screenshot, the woman in yellow is actress Verna Bloom. Her fictional character, Eileen, heads to the site of the DNC looking for assistance. Instead, she finds herself in Grant Park and off Michigan Avenue amidst (very real) riots. Note: the men in the background of this screenshot are not actors, but actual law enforcement.

There, the character/actress—along with Wexler’s camera and, therefore, you, the viewer—witnesses genuine acts of police brutality. In fact, Wexler says he was tear-gassed by National Guardsmen during the shoot. 

You can watch most of the protest scenes in the (rather poor quality) montage below.