I watched this movie in early '90s. The main character gets into different films (but I'm not sure). There was definitely a scene where he drives a car with the Nazis and decides to play dice to decide who will jump. The Nazi rolls a '6' and the guy rolls a '7' (on a 6-digit die)!!! The Nazi jumps out.
That would be German 1985 comedy movie "Die Einsteiger" (loosely translated as The Get-In-ers? No idea of an official English name)
Storyline from IMDB site:
Movie fan Mike has invented a machine with which he is able to take part in every movie which is currently running on his video tape recorder. But he and his friend Tommy are watched while trying out this new device and soon two electronic companies are on their trail to discover the secret of this invention.
The scene with main characters playing dice with Nazis in a truck is supposed to look as if taken from an Indiana Jones movie, playing from a videocassette, to which the main characters were transported in using the device.