Here's my playlist so far. Please add suggestions and try to limit them previously unlisted artists.

I tried to have some order, pop first, then oldies at the end.

Akon - Don't Matter
Shaggy - Angel
Sugar Ray - Girls Were Made to Love
Sugar Ray - Fly
Sublime - Santeria
Weezer - Island In The Sun
Sugar Ray - Under The Sun
Big B - Sinner
Big B - Let's Go Play
OMC - How Bizzare
LFO - Summer Girls
The Dirty Heads - Stand Tall
Sugar Ray - Into Yesterday
311 - Speak Easy
311 - Amber
Sublime - Doin' Time
Ai Otsuka - Kokonatsu Vacation
No Doubt - Underneath It All
Train - Hey, Soul Sister
Jason Mraz - I'm Yours
The Dirty Heads - Lay Me Down
The Expendables - Down, Down, Down
Dispatch - The General
State Radio - Right Me Up
Sugar Ray - Boardwalk
Sugar Ray - Even Though
Everclear - The Honeymoon Song
UB40 - Red Red Wine
Don Carlos - Spread Out
Don Carlos - Laser Beam
John Lennon - Bring on The Lucie (Freda Peeple)
The Beach Boys - Wouldn't It Be Nice
The Beach Boys - Kokomo
Rupert Holmes - Escape (The Pina Colada Song)
Stampeders - Sweet City Woman
Israel Kamakawiwo'ole - Somewhere Over The Rainbow & What A Wonderful World
Riveras - California Sun
Ventures - Brown Eyed Girl
Ventures - Music To Watch Girls By