I had an odd experience during a road trip in my teens which helped me decide on my final listen. I was in the back row of seats in my mom's van, her ride of choice before her mid-life crisis convinced her to switch it out for a cherry red Dodge Charger. Anyway, the windows were all cracked which let a nice breeze flow through the car. A particularly soft, refreshing one lifted my shirt just enough to pass around my skin as Gordon Lightfoot's Wreck of the Edmund Fitzgerald droned from the speakers. It was only a moment but I'd never felt that peaceful and carefree before or since.
Or, being the fickle fuck that I am, I'd also pick Brain Damage/Eclipse - from an album I listened to during stuffy, lethargic Summer Vacation days. When laying around doing nothing didn't come with a huge side order of existential shame.