Peter Outerbridge (and Wendy Crewson) in ESCAPE VELOCITY (a movie I actually watched a while ago, btw. Voluntarily. Honest.)
And really, I thought it couldn't get much better than this. But then I found
David Marciano (and Stephanie Romanov) in DARK SPIRAL It's a close second. Very close.
Unlike Escape Velocity it has that student film charm, kinda Purple Toast-ish. Without the music. It makes up for it with the Most Terrible Sound Ever. I recommend to watch with headphones if you want to really appreciate this one.
Btw, the trailers are 3.5 and 5.5 minutes, respectively. They just seem longer.