Five is tough.
Aguirre, the Wrath of God (Werner Herzog, 1972)
Bad Boy Bubby (Rolf de Heer, 1993)
Badlands (Terrence Malick, 1973)
The Beaver Trilogy (Trent Harris, 2001)
The Brown Bunny (Vincent Gallo, 2003)
Dont Look Back (D. A. Pennebaker, 1967)
Los Olvidados (Luis Buñuel, 1950)
Naked (Mike Leigh, 1993)
Paris, Texas (Wim Wenders, 1984)
What is it? (Crispin Glover, 2005)