I'm writing a screenplay based on some not so pleasant experiences I had during high school, primarily my senior year so I'm looking at finding different songs from those years to take me back and get the juices flowing. Songs that I listened to back then include:

All the Small Things - Blink 182
Bye Bye Bye - Nsync
Oooops, I Did It Again - Britney Spears (the whole album on that one)
It Wasn't Me - Shaggy
Say My Name - Destiny's Child
The Shape of My Heart - BSB
Thank God I Found You - Mariah Carey
The Real Slim Shady - Eminem
Smooth - Santana and Rob Thomas
Cold Day in July - The Dixie Chicks

Just making this list has brought back tons of memories! :)

Shimmer by Fuel and Pretty Fly (for a White Guy) by The Offspring come to mind.

You must include the 'Thong Song' at some point.

Didn't Limp Bizkit come out full force around that time?

Songs/bands that make me think of high school (graduated 1999) :
Eve 6 (they played at the venue my senior prom was held at the night before our prom)
Lit
Eagle Eye Cherry "Save Tonight"
Ricky Martin-Livin' La Vida Loca
Ben Folds Five- Brick
Verve- Bittersweet Symphony

Found this helpful:
http://en.wikipedia.org/wiki/1999_in_music

(And I realized I loved so much of the music that came out that year! The first Guster album I heard was from that year!)

In May 2000, a pop song came out called Graduation (Friends Forever) by Vitamin C. It's been played at graduations ever since. It might be good for a final scene.

Also, you may want to look into Spice Girls and A*Teens.

Wasn't that about the time that Ronan Keating's "When you say nothing at all" was playing on the radio? Oh and that "Kiss me" song, too. It was from Six Pence None the Richer or something like that, can't remember if the name was exactly like that. I think J.Lo was a big thing somewhere around that time, "Waiting for Tonight" had a music video in which they celebrated the new millenium. That brings the whole millenium theme: Robbie Williams' "Millenium" and Backstreet Boys had an album called "Millenium", included songs like "Show me the meaning", "I want it that way", "Larger than life" etc.

Btw. wasn't Eifel 65's song Blue released around that time? You should also check the soundtracks of the movies made then, for example "10 things I hate about you", "She's all that" and "Notting Hill".

Ah, my freshman year of high school. I distinctly remember that Korn and Limp Bizket were huge then, Kid Rock was just coming out. I made the somewhat mistaken prediction that Britney Spears would never last. Hmm...who else do I remember? (Yes, I'm using Wikipedia for this little trip down memory lane.)

JLo, Destiny's Child and Christina Aguilara all started. Then Pink became the b*tchy pop girl who made fun of them all.
Everyone was in love with Dave Matthews.
Remember Silverchair? "Ana's Fire" was big, but "Anthem for the Year 2000" might work better for your script.
My friends and I loved Ben Folds (it was still Ben Folds Five then).
How about Ricky Martin? Enrique Iglesias? Oh, the Latin Invasion.
Red Hot Chili Peppers - Californication.
Macy Gray! That song was everywhere!
Do you remember the music video for Robbie William's "Rock DJ?" It blew my teenage mind.
Mambo No. 5. Enough said.
Roughriders at high school dances. We knew all the words.
"The Bad Touch." Again, we knew all the (highly inappropriate for our age) words.
Rage Against the Machine did "Guerilla Radio." A million little anarchists were born.
Foo Fighters had mainstream hits!
TLC "No Scrubs"
Smash Mouth!
The Goo Goo Dolls got big.
Remember Baz Luhrman "Everybody's Free to Wear Sunscreen" and then Chris Rock did "No Sex in the Champagne Room"
Fatboy Slim - "Praise You"
Everlast - "What It's Like" I can't believe I forgot about that song.
No Doubt finally released "Return of Saturn"
The White Stripes and The Hives came out, but it took everyone a year or two to "discover" them.
Papa Roach - "Last Resort"

And that pretty well covers things to mid-2000.
Wow, I had way too much fun going through all that.

Heh, I remember the music from those years. :D I remember a lot of these...here's some of mine:

Jesse Hold On - B*witched
Graduation (Friends Forever) - Vitamin C

And of course the ones already mentioned. :)

Ooh...don't forget Aaron Carter (especially Aaron's Party)! He had some real fun dance music.

most definitely! i forgot about that!

TLC had a couple songs, like "No Scrubs". And there's "Mambo Number 5" and "Steal my Sunshine" by Len~

I like the album Britney Spears - Baby One More Time . He was released in 1999, when Britney was still quite a child. At that time, her thoughts were pure, and the voice - gentle.