Version 1.0.0.1 (Classic) can sometimes have issues on modern hardware. Here are a few "helpful" tips to ensure your story progression isn't interrupted:
In one late-game chapter, you need to raise a large sum of money ($27,500). Instead of grinding small jobs, use Mike Bruski’s Scrapyard to crush cars; it is the fastest way to get the cash needed to trigger the next story beat.
The provides a gritty cinematic experience following the rise of Vito Scaletta through the ranks of the Italian mob . To help you get the most out of the story and this specific version, The Core Story: Vito's Rise and Fall