Road trips have changed a lot in my life! They only started building the first big motor-ways here in the last 15 years, so before that we used to have to drive through dozens of small towns connected by little windy roads (with HUGE traffic jams)
A lot of the time we would just listen to the radio and you could kinda tell where you were based on how the reception would fade (it always felt like an adventure when our local station would turn into fuzz), then you'd have to settle for the weird radio stations you'd pick up along the way, we had a preferred station for each part of the country! My parents got an iPod in 2002 and it could last a whole 6 hours per charge with an iTrip radio transmitter attached. That made diving-music much more eclectic.
In keeping with the 80s theme though, we always had a tape of Sparkle in the Rain by Simple Minds in the car as a backup and it got played a lot - it stuck around in my dads car after their breakup but I remember it turning to blue smoke in the stereo when we got in a crash once (don't worry no one was hurt but the car) ~ I still really associate it with life around 2000.
Waterfront by Simple Minds
My last memories of the small roads fade out around 2006 but they are really connected with the songs that my mum was playing back then:
Hotel Song by Regina Spektor
After the big roadways were built everything got more futuristic

The new roads sort of cut through the countryside on a ramp so it feels like you're flying - I don't drive, but the last few trips I've been on my with mum, she's started a tradition of listening to 90s trance music and pretending to be in a space ship