Songs you could easily listen to more than once, or twice, or thrice...

MrsExpendable does this and it bugs the piss out of me, but I have a few I guess.

Boat Drinks -- Jimmy Buffett (when I'm driving in the snow)
2112 -- Rush
Simple Kind of Man -- Lynyrd Skynyrd

 

Also, Breakout by Foo Fighters.

 

Love hearing "hero" by the Foo Fighters, too.

 

Ten by D.J. Sun
Policy of Truth by Depeche Mode
Joining You by Alanis Morrisette
Follow the Leader, Paid in Full by Eric B. and Rakim
A Little More Love by Olivia Newton-John
White Town by White Town
Lucky Man by The Verve
Uplift by Rakim
Black by Pearl Jam
West End Girls by Pet Shop Boys
Still No. 1 by Boogie Down Productions
Go See the Doctor by Kool Moe Dee
Life in a Northern Town by Dream Academy
Holiday in Cambodia by the Dead Kennedys
What's the Story (Morning Glory) Oasis; but really, any number of songs by Oasis
Amber and I'll Be Here Awhile by 311
Jeopardy by Greg Kihn Band
Hot for Teacher by Van Halen
Always on My Mind by Elvis Presley
Paul Revere by the Beastie Boys
the entire song list (except the third song) on Electric Honey by Luscious Jackson
Love Will Keep Us Together by Captain and Tenille
Something About Us, Da Funk by Daft Punk

I'll think of more as the day unfolds.

 

the rain song - led zeppelin. one of the best songs ever created, in this man's opinion.

 

goin' to california - zep

 

Amarillo by Morning, George Strait
Several songs by Johnny Cash and Alabama
Money For Nothin'
Appetite for Destruction

 

Gotta say, it cracks me up to see "Jackie Wilson Said" and "I Can't Stand Up For Falling down" listed next to a Whitesnake song. ;D

My partial list:

7:30 by the Pernice Brothers
Flaming Wreck by the Pernice Brothers
Riot Act by Elvis Costello
Sweet Dreams by Split Enz
Recurring Dream by Crowded House
Landed by Ben Folds
My Brilliant Feat by Colin Hay
Waltz #2 (XO) by Elliott Smith
Ballad of El Goodo by Big Star
Backstabbers by The O'Jays
The Only One I Know by The Charlatans
Hayfever by Trashcan Sinatras
Adelaide by Paul Kelly
Honey Don't Think by Grant Lee Buffalo
Throw Your Arms Around Me by Hunters & Collectors
Belly of the Whale by Burning Sensations
Forever by Little Steven & the Disciples of Soul

 

"I Can See Clearly Now", Johnny Nash
"Bust a Move", Young MC
"A Quick One", The Who
"The Weight", The Band
"Big Me", Foo Fighters
Side 2 - Abbey Road (or for you young uns in the audience, starting with Here Comes the Sun)

 

There are just some songs that when I hear them are ones I'll always listen to over and over and never get tired of (Police, Rush, Joe Satriani, Eric Johnson, most stuff by Pearl Jam, etc.) but here's a few that aren't from the aforementioned artists, but are songs from artists I've never bought their albums/tapes/CDs/anything:

Bruce Springsteen -- Brilliant Disguise
Rod Stewart -- You're in My Heart
T'Pau -- Heart and Soul (guilty pleasure)
Madonna -- Live to Tell