I think of 3 off the top of my head: (1969) The Italian Job: 3 Mini Coopers (1971) Duel:Huge Oil Tanker & Plymouth Valiant (1993) Slaughter of the Innocents: An ark. (Yes, someone is in it) I don't have a video but a screenshot from the trailer which only shows a small clip A lot of the game reminds me of these films, and have even seen some homages to it. What other films/TV can you think of that have epic cliff drops.
Back to the Future 3 has one with a train, though since it was done with a model you don't actually get to see it hit the ground. A tank goes over a cliff in Indiana Jones and the Last Crusade, though, again, you don't get to see the carnage. Stupid as it is, the aggressively silly 80's British variety show 'the Young Ones' concluded its brief run with a stolen double-decker bus plowing through a billboard advertising a Cliff Richards concert, then tumbling into a quarry.
Battletruck (a.k.a. Warlords of the 21st Century) Death Race 2000 Groundhog Day The Lost World: Jurassic Park (the trailer dangles for some time but can't remember how much they show of it falling off) The Spy Who Loved Me The Wraith I'm sure I've seen many I can't specifically recall.