oooh....my 80's list has a few hundred songs.
Something more simple. The mix I play when I have friends over on a summer night and it's late and we're hanging out on the beach with a bonfire going:
Harvest Mood - Neil Young
Bobcaygeon - The Tragically Hip
Get Out The Map - Indigo Girls
Heart of Gold - Neil Young
Castles Burning - Crosby, Stills, Nash and Young
Sleep While I Drive - Melissa Ethridge and KD Lang
Big Yellow Taxi - Joni Mitchell
Just A Kiss - KD Lang
Sunday Morning Coming Down - Kris Kristofferson
I Am A Rock - Simon and Garfunkel
The Rain Song - Led Zeppelin
Hey There Delilah - Plain White T's
Fool in the Rain - Led Zeppelin
Old Man - Neil Young
Black Bird - Sarah MacLachlan
Son of a Preacher Man - Joan Osborne
Mrs. Robinson - Simon and Garfunkel
Solsbury Hill - Peter Gabriel
Soul Child - Shawn Mullins
Out on the Weekend - Neil Young
Magic - Bruce Springsteen
Beautiful Wreck - Shawn Mullins
I have just about every genre except death metal. I have over 200 playists. Uhm. yeah.....I'm addicted.