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

If you're looking into some summer/surf music, I would look into Bob Marley and Shaggy
Especially Boombastic

Ah, well, I don't want to add pure reggae.

I ought to look into Damien Marley for modern, and throw Bob into the oldies section.

Surf playlist without Dick Dale or The Ventures?
Blasphemy.

Some suggestions as the "oldies" part is lacking some classics.

The Trashmen - King of the Surf
The Barracudas - Summer Fun
The Triumphs - Surfside date

Kinda unrelated but still awesome
Lee Moses - Bad Girl

The best topic on music chat atm. ++

War_Hero, plz be specific. Also, Ventures is at the end there. It's because those are instrumental.
DaBandito, I'll check 'em out, thanks.

Although, I'm not trying to build the oldies section much because I'm sure theres tons of that. I'm mostly looking for modern influenced songs rather than classic sound.

I'd like to add some suggestions.

Atmosphere - Sunshine


The Expendables - Jenny


Fuel - Sunburn


Long Beach Dub Allstars - Rosarito


I hope you find something you like.