Dire Straits - Money for Nothing. It was on a cassette in my parents car. Not what I normally listen to, but it’s an alright song, and after having had to endure whatever my parents decided to listen to, that was what I decided to turn up on my first drive alone.
I think the first thing I brought into the car with the intent to listen to it while driving was Dream Theater - Awake, freshly recorded from CD onto tape