Best Songs of 1999

Just like I created 100-song Best of Lists representing 30, 20, and 10 years ago, I have spent the past year creating lists for every other year I've been alive. So rather than wait ten years to publish them all, I'm also going to share lists from 5, 15 and 25 years ago. I'd do 35, too, but that pesky Best of 1979 isn't quite finished yet.

In the past two years since I started this process of culling tracks from every year of my existence, I have come across a slew of great albums and artists that I had only heard of (but not heard), or, in a few cases, had never known about at all. It's been a wonderful experience, yet again, to piece together this list.

As before, this list is an honest attempt to assess a year in music, merging the reality of a list made 15 years later with the idea that, had I conceived of such a list at the time, I would have included pop hits, obscure tunes, aging favorites and new artists alike. This, more than most years, is a perfect example of that blend between the obscure and the massively popular.

For these year-end lists, I like to undertake the seemingly impossibly task of creating an hours-long mix. The order you see below represents that effort, which you can listen to via Spotify or my preferred streaming service, Rdio. Sadly all 100 tracks aren't available in either case, but you get the general idea. Track notes to come eventually or—particularly if last year's un-annotated lists are a sign of future action—maybe never.

Show Grid

Utopia Parkway

Fountains of Wayne

Utopia Parkway

Atlantic

Notes
Instant Pleasure

Rufus Wainwright

Big Daddy

American

Notes
Center of Attention

Guster

Lost and Gone Forever

Sire

Notes
Race for the Prize

The Flaming Lips

The Soft Bulletin

Warner Bros.

Notes
Spit on a Stranger

Pavement

Terror Twilight

Matador

Notes
Else

Built to Spill

Keep It Like a Secret

Warner Bros.

Notes
23-five

Michael

You Must Be This Tall

Ghostmeat

Notes
Wrapped in My Memory

Shawn Smith

Shield of Thorns

Establishmentstore

Notes
Picture in a Frame

Tom Waits

Mule Variations

Epitaph

Notes
Save Me

Aimee Mann

Magnolia

Reprise

Notes
Lolita

Martha Wainwright

Martha Wainwright EP

Querbes Service

Notes
Hot Rock

Sleater-Kinney

The Hot Rock

Kill Rock Stars

Notes
Fast As You Can

Fiona Apple

When the Pawn…

Work

Notes
…Baby One More Time

Britney Spears

…Baby One More Time

Jive

Notes
Candy

Mandy Moore

So Real

550 Music

Notes
What a Girl Wants

Christina Aguilera

Christina Aguilera

RCA

Notes
Bailamos

Enrique Iglesias

Enrique

Interscope

Notes
Waiting for Tonight

Jennifer Lopez

On the 6

Sony

Notes
Red Alert

Basement Jaxx

Remedy

Astralwerks

Notes
Feeling for You

Cassius

1999

Virgin

Notes
Get a Move On

Mr. Scruff

Keep It Unreal

Ninja Tune

Notes
N 2 Gether Now

Limp Bizkit featuring Method Man

Significant Other

Interscope

Notes
The Next Episode

Dr. Dre

2001

Aftermath

Notes
My Name Is

Eminem

The Slim Shady LP

Interscope

Notes
Thank You

Dido

No Angel

Arista

Notes
I Try

Macy Gray

On How Life Is

Epic

Notes
Do You Like the Way

Santana featuring Lauryn Hill & Cee-Lo

Supernatural

Arista

Notes
Just Can’t Make It

Maktub

Subtle Ways

Jasiri Media Group

Notes
The Next Movement

The Roots

Things Fall Apart

MCA

Notes
Ms. Fat Booty

Mos Def

Black on Both Sides

Rawkus

Notes
Hold On

Romanthony

Hold On 12"

Roule

Notes
I See You Baby (Fatboy Slim Remix)

Groove Armada

Vertigo

Zomba

Notes
Deceptacon

Le Tigre

Le Tigre

Mr. Lady

Notes
Let Forever Be

The Chemical Brothers featuring Noel Gallagher

Surrender

Astralwerks

Notes
Stoned

Smash Mouth

Astro Lounge

Interscope

Notes
Miserable

Lit

A Place in the Sun

RCA

Notes
For the Movies

Buckcherry

Buckcherry

Dreamworks

Notes
Ana’s Song (Open Fire)

Silverchair

Neon Ballroom

Epic

Notes
Adam’s Song

Blink-182

Enema of the State

MCA

Notes
I Want It That Way

Backstreet Boys

Millennium

Jive

Notes
Girl on TV

LFO

LFO

Arista

Notes
Millennium

Robbie Williams

The Ego Has Landed

Capitol

Notes
Will2K

Will Smith

Willennium

Columbia

Notes
Ooh La La

The Wiseguys

The Antidote

Wall of Sound

Notes
Beautiful Stranger

Madonna

Austin Powers: The Spy Who Shagged Me

Maverick

Notes
Cha Cha Cha (Go Remix)

Jimmy Luxury & The Tommy Rome Orchestra

Go

Sony Work

Notes
Steal My Sunshine

Len

You Can’t Stop the Bum Rush

Sony Work

Notes
Better Days

Citizen King

Mobile Estates

Warner Bros.

Notes
Stellar

Incubus

Make Yourself

Sony

Notes
Sour Girl

Stone Temple Pilots

No. 4

Atlantic

Notes
Can’t Change Me

Chris Cornell

Euphoria Morning

A&M

Notes
Learn to Fly

Foo Fighters

There Is Nothing Left to Lose

RCA

Notes
Map of New Jersey

Late Night Television

11 Love Songs for Your Shallow Broken Heart

self-released

Notes
Another True Fiction

Jeremy Toback

Another True Fiction

RCA

Notes
Trailways

Josh Joplin Band

Useful Music

SMG

Notes
High Life

Counting Crows

This Desert Life

Interscope

Notes
Help Myself

Dave Matthews Band

Scream 2

Capitol

Notes
Blue Moon Rising

Gomez

Liquid Skin

Virgin

Notes
Viva! Sea-Tac

Robyn Hitchcock

Jewels for Sophia

Warner Bros.

Notes
Army

Ben Folds Five

The Unauthorized Biography of Reinhold Messner

550 Music

Notes
Laugh I Could Learn to Love

Gus Black

Aware 7 The Compilation

Aware/Columbia

Notes
Lately

Shawn Mullins

The First Ten Years

Sony

Notes
Neon

John Mayer

Inside Wants Out

self-released

Rereleased by Sony in 2002
Counting on You

Train

One and a Half

Aware/Columbia

Notes
Heartbreakin Man

My Morning Jacket

The Tennessee Fire

Darla

Notes
Ready to Run

Dixie Chicks

Fly

Monument

Notes
Steal My Kisses

Ben Harper & The Innocent Criminals

Burn to Shine

Virgin

Notes
Every Morning

Sugar Ray

14:59

Lava

Notes
Never Let You Go

Third Eye Blind

Blue

Elektra

Notes
Nineteen

Old 97s

Fight Songs

Elektra

Notes
This Time

Los Lobos

This Time

Hollywood

Notes
The Road to Rock & Roll

Joe Strummer & the Mescaleros

Rock Art and the X-Ray Style

Epitaph

Notes
I Think I Need a New Heart

The Magnetic Fields

69 Love Songs

Merge

Notes
Keep a Lid on Things

Crash Test Dummies

Give Yourself a Hand

Vik

Notes
Nighttime

Ben Lee

Breathing Tornados

Grand Royal

Notes
Ladyfingers

Luscious Jackson

Electric Honey

Grand Royal

Notes
Alive

Beastie Boys

The Sounds of Science

Capitol

Notes
Vivrant Thing

Q-Tip

Amplified

Arista

Notes
Got Your Money

Ol’ Dirty Bastard

Nigga Please

Elektra

Notes
Say My Name

Destiny’s Child

The Writing’s on the Wall

Sony

Notes
No Scrubs

TLC

Fan Mail

LaFace

Notes
Love Is Blind

Eve

Ruff Ryders’ First Lady

Ruff Ryders

Notes
Thong Song

Sisqó

Unleash the Dragon

Def Soul

Notes
Debra

Beck

Midnite Vultures

DGC

Notes
Windowlicker

Aphex Twin

Windowlicker

Warp

Notes
Dry the Rain

The Beta Band

The Three EPs

Astralwerks

Originally released in 1997 on the UK-only Champion Versions EP
Coffee + TV

Blur

13

Food/Virgin

Notes
The Great Beyond

R.E.M.

The Great Beyond

Warner Bros.

Notes
Brothers and Sisters

Coldplay

Brothers & Sisters

Fierce Panda

Notes
Take a Picture

Filter

Title of Record

Reprise

Notes
Otherside

Red Hot Chili Peppers

Californication

Warner Bros.

Notes
Flowing

311

Soundsystem

Volcano

Notes
The City

The Dismemberment Plan

Emergency & I

DeSoto

Notes
Porcelain

Moby

Play

V2

Notes
Pass in Time

Beth Orton

Central Reservation

Arista

Notes
I See a Darkness

Bonnie ‘Prince’ Billy

I See a Darkness

Drag City

Notes
Ohio

Damien Jurado

Rehearsals for Departure

Sub Pop

Notes
When You Wake Up Feeling Old

Wilco

Summerteeth

Reprise

Notes
Underwater Life

Freedy Johnston

Blue Days Black Nights

Elektra

Notes
Last Kiss

Pearl Jam

Last Kiss

Epic

Notes