OK - major milestones then.

( The Disappointed Caravanner of the year, Wed 7 Sep 2011, 19:45, 2 replies, latest was 15 years ago)

I was trying to avoid thinking of songs with memories, as that'd change my answers a bit

( Agnostic Antichrist Baltimora, Wed 7 Sep 2011, 19:58, Reply)

I'm asking this
Because we have to take our five most significant tracks to my mate's 50th.

Maybe pivotal moments count. I've only got three so far.
( The Disappointed Caravanner of the year, Wed 7 Sep 2011, 20:01, Reply)

Ahh, I see
Fucking hell, that'd be an interesting variation from my mates and I.
( Agnostic Antichrist Baltimora, Wed 7 Sep 2011, 20:02, Reply)

1.When you're young - The Jam - A snapshot of my teens.
2.Please please please - The Smiths - A snapshot of my life.
3.No ordinary morning - Chicane - A reminder never to let a guy use me again.
4.Holiday in Cambodia - Dead Kennedys - A reminder that life can be fun.
5.The Low album - David Bowie - The album I played to death when I first suffered with depression at the age of 18.
( girlinthehole, Wed 7 Sep 2011, 19:58, Reply)

Top man BGB
That's my 4th - Holiday in Cambodia - because music can churn your guts up too, and because East Bay Ray's guitar work on that is so scary.
( The Disappointed Caravanner of the year, Wed 7 Sep 2011, 20:05, Reply)

The Dead Kennedys make me wish I hadn't been such a wuss as a teenager and been a proper punk.

( girlinthehole, Wed 7 Sep 2011, 20:07, Reply)

I was a couple of years too young
My cousin Steve saw the Pistols at Lancaster on their last gig before McLaren saw fit to split them up and insert Sid "Simon Ritchie" Viscious.
( The Disappointed Caravanner of the year, Wed 7 Sep 2011, 20:12, Reply)