I ran with a few different crowds in high school, and as such have a bunch of different songs that don't really seem to fit together, but they really resonate with me:
Transplants - "Diamonds and Guns"
Sublime - "40oz. to Freedom" and "Santeria"
T.I. - "Bring Em Out" ... My friend had this big cordless iHome that we'd carry off the bus when we arrived at our golf matches and my iPod would be hooked up playing this song
Green Day - "Jesus of Suburbia" and "Basket Case"
Violent Femmes - "Good Feeling"
Nas - "Ether"
Michael Jackson - "Billie Jean"
The Who - Baba O'Reily
Rush - "Prime Mover"
The Gaslight Anthem - "Meet Me By the River's Edge"
Foo Fighters - "Everlong"
Unk - "2 Step (Remix)"
And then pick any top 40 R&B/Hip-hop song from my four years in high school and I can probably recite every word of each one from the sheer amount of times they were played at parties.
Oh, and can't forget:
Cascada - Everytime We Touch