Oh God, this thread brings back bad memories:
In the original NFS: Underground, one of the last races is a 7-lap endurance, with each lap taking approx 5 minutes with a fully upgraded and tuned car.
Every single lap your opponent(head-to-head) will take a short-cut right before the finishing line. If you don't take it, regardless of your lead before passing to turn-off, the bastard would always come out far enough ahead of you to beat you to the finishing line.
Then, after conditioning the player to always take the short-cut to avoid losing the lead, on the final lap, the game spawns a panel-van sideways across the short-cut, blocking it entirely. Player car smacks into the van, coming to a dead stop. Your opponent, however, doesn't take the short-cut for the first time in 7 laps and cruises to an easy victory.
I still instinctively swerve when I'm driving now and see a panel-van!