Good idea although it's difficult to restrict it to just five. Difficult to say also since I lost and rebuilt my music collection (both physical and digital) several times over the course of the years but I'm pretty sure these are at least in the top ten:
Mobb Deep - The Infamous/Hell on Earth
Capital D - Insomnia
X-Raided - Unforgiven
Z-Ro - Look what you did to me
Kery James - Si c'était à refaire
I've listened to The Infamous maybe a handful of times in the last couple years but it's still most likely #1, was more or less the soundtrack of my youth. The others are interchangeable and there's another handful of albums that I listened to roughly as much.