Something from Throwing Copper by Live, such as “Lightning Crashes”, “Iris”, or “I Alone”
Only five you say…
- Summer Babe - Pavement
2)Sugar Kane - Sonic Youth
3)Hey Ladies - Beastie Boys (released in 1989, but listened to throughout the 90s)
4)Dig for Fire - Pixies
5)At the Hundreth Meridian - Tragically Hip
Honorable mention
Connected - Stereo MCs
Summing up the nineties for me are:
Portishead - Sour Times
Massive Attack - Protection
Orbital - Chime
Leftfield - Song of Life
Underworld - Rez
A lot of my favorites have been mentioned, but I’ll add:
“Mr. Jones” - Counting Crows
“Nothing Compares 2 U” - Sinead O’Connor
"Fade Into You’ - Mazzy Star
“Groove Is In the Heart” - Deee-Lite
“Unbelievable” - EMF
And however much I’d like to erase them from history, no 90s compilation would be complete without Hootie & the Blowfish.
This is gonna be mid to late 90s:
- Hey, Macarena!
- Flagpole Sitta (Harvey Danger)
- The Way (Fastball)
- One Headlight (Wallflowers)
- How Bizarre (O.M.C.)
Good choice, that is such a nineties tune. 
Well, since alt-rock/grunge has been well covered:
Dre Day - Dr Dre
Who Am I (What’s My Name) - Snoop Dogg
Insane in the Brain - Cyprus Hill
Jump Around - House of Pain
Mo’ Money, Mo’ Problems - Notorious BIG / Puff Daddy
- Groove is in the Heart - Deee-lite
- Sour Times - Portishead (or anything from Dummy)
- Open Up - Leftfield (or anything from Leftism)
- Firestarter - Prodigy
- Loaded - Primal Scream
No space sadly for Transglobal Underground, Underworld, Dreadzone, Bjork …
THE top 5 has definitely already been mentioned (Nirvana, Hootie, Pearl Jam, Alanis and Blind Melon). But here’s a few that would also belong…
- Spice Girls - Wannabe (Shut up! It was popular! Not that I would know…)
- Hanson - MMMbop (Seriously! Hanson was huge! Again, not that I liked them or anything…)
- 4 Non Blondes - What’s Up
- Ben Folds Five - Brick
- Collective Soul - Shine
I could probably go 30 more, so we’ll just leave it at that now.
The following five songs would be definitive of the Pop music of the 90’s as demonstrated by their reflection of either long-lastingness or importance of the singer/group to the decade:
- Macarena - Del Los Rios Come on, I mean, they STILL play the damn thing…
- *One Sweet Day * - Mariah Carey and Boyz II Men The ultimate in the group croon
- *I Will Always Love You * - Whitney Houston Played endlessly, and contains the sound of the early 90’s
- Smooth - Santana (f/Rob Thomas) Played endlessly to end the decade, showing the shift beginning to put an end to 90’s sameness
- *Vision of Love * - Mariah Carey I hate to have her here twice, but she WAS the 90’s in AC/pop music
Now, if you want the songs that, in my mind, I will forever associate with the 90’s? Different list, personal to me.
Includes, among others, *Truly Madly Deeply * by Savage Garden, *Foolish Games * (the album version, not the godawful radio rendition) by Jewel, Hero by Mariah Carey, *3 am * by Matchbox 20 (the beginnings of a return to musical differentiation by pop music stars after the wilderness years of the 80s and early 90s) …
High - The Cure
Qkumba Zoo - The Child Inside
Sweet Lullaby - Deep Forest
Return to Innocence - Enigma
Sweet Dreams (Are Made of This)- Marylin Manson
(ETA: I can’t believe no one mentioned NIN yet!)
How could I forget, The Downward Spiral was my first CD. I also can’t believe I didn’t submit Sublime. Thanks to you all, I’m currently forming a 90s playlist.
Closer[to God] by Nine Inch Nails
What I Got by Sublime
Amber by 311
Buddy Holly by Weezer
Cotton Eye Joe by Rednex
Great suggestion. I might have to dig around and find that cd now!
Brendon Small
Sorry to double post - I missed the edit window by a mile and a half.
Another good 90’s song is Anthem for the Year 2000 by Silverchair - it was a 90’s song with a expiration date!
Also, Fuel - Bittersweet
Brendon Small
Great question! This was tough, so many came to mind! But as per the rules of the OP;
Smells Like Teen Spirit - Nirvana
Tubthumping - Chumbawumba
3AM - Matchbox 20
Lovefool - The Cardigans
Paula Cole-I Don’t Want to Wait