The Seal of Nehahra (2000)
The Seal of Nehahra is an American film made in 2000, created by Mindcrime Productions as part of the Nehahra Project. Made using a modified version of id Software's 1996 first-person shooter computer game Quake and released over the Internet as a non-interactive game demo package, the film was the longest released Quake movie — as Quake-based machinima was known at the time. At a total length of three hours and fifty five minutes, it is the longest single-piece machinima production . The film received high reviews from the major Quake movie review sites of the time, Psyk's Popcorn Jungle and The Cineplex.
More at Wikipedia.