Inspired by Michael Renov’s discussion of the “collision of history and fiction” in Haskell Wexler’s Medium Cool and Ross McElwee’s meditation on a Hollywood melodrama based on his great-grandfather, I have found myself increasingly fascinated by films that grapple with the boundary between fiction and non-fiction or that test raise questions about how we come to know and experience the world. To that end, I have assembled a series of films that tackle those very difficult questions from a variety of angles. On the one hand, these films include documentaries that make use of fictional elements (Radiant City), raise questions about what it means to be a witness (Winter Soldier, The Devil Came on Horseback), or seek to engage with our experience of public space (Helvetica, Sans Soleil). On the other hand, fictional films such as Medium Cool incorporate documentary elements into the fictional narrative. Finally, a film such as Richard Linklater’s Waking Life, with its use of rotoscope animation to depict a character’s “waking dream,” shatters these categories altogether. But all of these films raise important questions about what counts as documentary and about what role documentary can serve in making sense of the historical world.