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
via past experience library: 7/9/2004

Notes
Instant Pleasure

Rufus Wainwright

Big Daddy

American
via past experience library: 12/3/2003 (TK)

Notes
Center of Attention

Guster

Lost and Gone Forever

Sire
via past experience library: 10/31/2003 (TK)

Notes
Race for the Prize

The Flaming Lips

The Soft Bulletin

Warner Bros.
via past experience library: 12/8/2007

Notes
Spit on a Stranger

Pavement

Terror Twilight

Matador
via past experience, the Nickel Creek cover (2002) library: 10/2/2006

Notes
Else

Built to Spill

Keep It Like a Secret

Warner Bros.
via my sister library: 8/4/2008

Notes
23-five

Michael

You Must Be This Tall

Ghostmeat
via retroactive experience library: 7/23/2005

Notes
Wrapped in My Memory

Shawn Smith

Shield of Thorns

Establishmentstore
via retroactive experience library: 10/20/2009

Notes
Picture in a Frame

Tom Waits

Mule Variations

Epitaph
via past experience library: 9/10/2005

Notes
Save Me

Aimee Mann

Magnolia

Reprise
via Magnolia (1999) library: 11/4/2010

Notes
Lolita

Martha Wainwright

Martha Wainwright EP

Querbes Service
via live in concert (2001) library: 11/1/2003 (TK)

Notes
Hot Rock

Sleater-Kinney

The Hot Rock

Kill Rock Stars
via retroactive experience library: 5/12/2012

Notes
Fast As You Can

Fiona Apple

When the Pawn…

Work
via past experience library: 10/29/2003 (TK)

Notes
…Baby One More Time

Britney Spears

…Baby One More Time

Jive
via TRL on MTV library: 12/6/2009

Notes
Candy

Mandy Moore

So Real

550 Music
via TRL on MTV library: 10/22/2009

Notes
What a Girl Wants

Christina Aguilera

Christina Aguilera

RCA
via TRL on MTV library: 11/1/2003 (TK)

Notes
Bailamos

Enrique Iglesias

Enrique

Interscope
via TRL on MTV library: 12/6/2009

Notes
Waiting for Tonight

Jennifer Lopez

On the 6

Sony
via TRL on MTV library: 10/22/2009

Notes
Red Alert

Basement Jaxx

Remedy

Astralwerks
via TK library: 5/19/2011

Notes
Feeling for You

Cassius

1999

Virgin
via TK library: 5/19/2012

Notes
Get a Move On

Mr. Scruff

Keep It Unreal

Ninja Tune
via TK (that TV spot though) library: 2/25/2007

Notes
N 2 Gether Now

Limp Bizkit featuring Method Man

Significant Other

Interscope
via TRL on MTV library: 10/29/2012

Notes
The Next Episode

Dr. Dre

2001

Aftermath
via past experience library: 5/11/2012

Notes
My Name Is

Eminem

The Slim Shady LP

Interscope
via TRL on MTV library: 10/31/2009

Notes
Thank You

Dido

No Angel

Arista
via the Eminem sample library: 5/17/2012

Notes
I Try

Macy Gray

On How Life Is

Epic
via TRL on MTV library: 5/24/2012

Notes
Do You Like the Way

Santana featuring Lauryn Hill & Cee-Lo

Supernatural

Arista
via past experience, but also “Smooth” library: 11/12/2003 (TK)

Notes
Just Can’t Make It

Maktub

Subtle Ways

Jasiri Media Group
via 103.7 The Mountain library: 11/12/2003 (TK)

Notes
The Next Movement

The Roots

Things Fall Apart

MCA
via past experience library: 11/3/2003 (TK)

Notes
Ms. Fat Booty

Mos Def

Black on Both Sides

Rawkus
via TK library: 6/11/2011

Notes
Hold On

Romanthony

Hold On 12"

Roule
via retroactive experience (Daft Punk) library: 5/19/2013

Notes
I See You Baby (Fatboy Slim Remix)

Groove Armada

Vertigo

Zomba
via TK library: 9/19/2009

Notes
Deceptacon

Le Tigre

Le Tigre

Mr. Lady
via TK library: 10/9/2017

Notes
Let Forever Be

The Chemical Brothers featuring Noel Gallagher

Surrender

Astralwerks
via MTV library: 7/29/2005

Notes
Stoned

Smash Mouth

Astro Lounge

Interscope
via 107.7 The End library: 12/19/2010

Notes
Miserable

Lit

A Place in the Sun

RCA
via 107.7 The End, MTV library: 7/14/2009

Notes
For the Movies

Buckcherry

Buckcherry

Dreamworks
via MTV library: 12/4/2010

Notes
Ana’s Song (Open Fire)

Silverchair

Neon Ballroom

Epic
via past experience library: 11/19/2009

Notes
Adam’s Song

Blink-182

Enema of the State

MCA
via TRL on MTV library: 10/20/2008

Notes
I Want It That Way

Backstreet Boys

Millennium

Jive
via past experience, TRL on MTV library: 9/4/2009

Notes
Girl on TV

LFO

LFO

Arista
via TRL on MTV library: 10/22/2009

Notes
Millennium

Robbie Williams

The Ego Has Landed

Capitol
via TRL on MTV library: 10/31/2009

Notes
Will2K

Will Smith

Willennium

Columbia
via past experience library: 10/22/2009

Notes
Ooh La La

The Wiseguys

The Antidote

Wall of Sound
via Big Daddy (1999) library: 12/3/2003 (TK)

1998 UK release / 1999 US release
Beautiful Stranger

Madonna

Austin Powers: The Spy Who Shagged Me

Maverick
via past experience library: 12/3/2003 (TK)

Notes
Cha Cha Cha (Go Remix)

Jimmy Luxury & The Tommy Rome Orchestra

Go

Sony Work
via Go (1999) library: 12/9/2010

Notes
Steal My Sunshine

Len

You Can’t Stop the Bum Rush

Sony Work
via MTV library: 9/10/2005

Notes
Better Days

Citizen King

Mobile Estates

Warner Bros.
via TK library: 11/12/2003 (TK)

Notes
Stellar

Incubus

Make Yourself

Sony
via TRL on MTV library: 11/1/2003 (TK)

Notes
Sour Girl

Stone Temple Pilots

No. 4

Atlantic
via past experience library: 10/5/2010

Notes
Can’t Change Me

Chris Cornell

Euphoria Morning

A&M
via past experience library: 3/6/2010 (TK)

Notes
Learn to Fly

Foo Fighters

There Is Nothing Left to Lose

RCA
via past experience library: 11/11/2003

Notes
Map of New Jersey

Late Night Television

11 Love Songs for Your Shallow Broken Heart

self-released
via Amazon MP3 (2005) library: 7/23/2005

Notes
Another True Fiction

Jeremy Toback

Another True Fiction

RCA
via 103.7 The Mountain library: 11/12/2003 (TK)

Notes
Trailways

Josh Joplin Band

Useful Music

SMG
via Aware 7: The Compilation (1999) library: 11/11/2003 (TK)

Notes
High Life

Counting Crows

This Desert Life

Interscope
via past experience library: 10/30/2003 (TK)

Notes
Help Myself

Dave Matthews Band

Scream 2

Capitol
via past experience library: 5/15/2004

Notes
Blue Moon Rising

Gomez

Liquid Skin

Virgin
via retroactive experience library: 3/15/2006

Notes
Viva! Sea-Tac

Robyn Hitchcock

Jewels for Sophia

Warner Bros.
via TK library: 8/9/2010

Notes
Army

Ben Folds Five

The Unauthorized Biography of Reinhold Messner

550 Music
via past experience library: 10/30/2003 (TK)

Notes
Laugh I Could Learn to Love

Gus Black

Aware 7 The Compilation

Aware/Columbia
via Aware 7 The Compilation (1999) library: 11/22/2003 (TK)

Notes
Lately

Shawn Mullins

The First Ten Years

Sony
via past experience library: 11/11/2003 (TK)

Notes
Neon

John Mayer

Inside Wants Out

self-released
via retroactive experience library: 11/9/2003 (TK)

Rereleased by Sony in 2002
Counting on You

Train

One and a Half

Aware/Columbia
via past experience library: 11/13/2003 (TK)

Notes
Heartbreakin Man

My Morning Jacket

The Tennessee Fire

Darla
via retroactive experience library: 7/23/2005

Notes
Ready to Run

Dixie Chicks

Fly

Monument
via the ether library: 5/12/2012

Notes
Steal My Kisses

Ben Harper & The Innocent Criminals

Burn to Shine

Virgin
via past experience library: 10/31/2003 (TK)

Notes
Every Morning

Sugar Ray

14:59

Lava
via TRL on MTV library: 10/22/2009

Notes
Never Let You Go

Third Eye Blind

Blue

Elektra
via past experience library: 10/18/2010

Notes
Nineteen

Old 97s

Fight Songs

Elektra
via past experience library: 11/1/2003 (TK)

Notes
This Time

Los Lobos

This Time

Hollywood
via past experience library: 11/12/2003 (TK)

Notes
The Road to Rock & Roll

Joe Strummer & the Mescaleros

Rock Art and the X-Ray Style

Epitaph
via TK library: 7/23/2005

Notes
I Think I Need a New Heart

The Magnetic Fields

69 Love Songs

Merge
via TK library: 7/9/2009

Notes
Keep a Lid on Things

Crash Test Dummies

Give Yourself a Hand

Vik
via 103.7 The Mountain, past experience library: 7/22/2010

Notes
Nighttime

Ben Lee

Breathing Tornados

Grand Royal
via past experience library: 10/26/2003 (TK)

Notes
Ladyfingers

Luscious Jackson

Electric Honey

Grand Royal
via past experience library: 11/12/2003 (TK)

Notes
Alive

Beastie Boys

The Sounds of Science

Capitol
via past experience library: 5/24/2013

Notes
Vivrant Thing

Q-Tip

Amplified

Arista
via past experience (A Tribe Called Quest) library: 4/28/2011

Notes
Got Your Money

Ol’ Dirty Bastard

Nigga Please

Elektra
via MTV library: 6/11/2011

Notes
Say My Name

Destiny’s Child

The Writing’s on the Wall

Sony
via TRL on MTV library: 10/22/2009

Notes
No Scrubs

TLC

Fan Mail

LaFace
via past experience library: 10/31/2009

Notes
Love Is Blind

Eve

Ruff Ryders’ First Lady

Ruff Ryders
via TRL on MTV library: 12/20/2010

Notes
Thong Song

Sisqó

Unleash the Dragon

Def Soul
via TRL on MTV library: 10/31/2009

Notes
Debra

Beck

Midnite Vultures

DGC
via past experience library: 11/12/2003 (TK)

Notes
Windowlicker

Aphex Twin

Windowlicker

Warp
via TK on MTV library: 9/24/2008

Notes
Dry the Rain

The Beta Band

The Three EPs

Astralwerks
via High Fidelity (1999) library: 11/2/2003 (TK)

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

Blur

13

Food/Virgin
via past experience, MTV library: 11/11/2003 (TK)

Notes
The Great Beyond

R.E.M.

The Great Beyond

Warner Bros.
via past experience library: 11/13/2003 (TK)

Notes
Brothers and Sisters

Coldplay

Brothers & Sisters

Fierce Panda
via retroactive experience library: 9/23/2006

Notes
Take a Picture

Filter

Title of Record

Reprise
via MTV library: 1/25/2009

Notes
Otherside

Red Hot Chili Peppers

Californication

Warner Bros.
via past experience library: 10/26/2003 (TK)

Notes
Flowing

311

Soundsystem

Volcano
via past experience library: 12/7/2004

Notes
The City

The Dismemberment Plan

Emergency & I

DeSoto
via retroactive experience library: 11/9/2003 (TK)

Notes
Porcelain

Moby

Play

V2
via the ether library: 11/5/2003 (TK)

Notes
Pass in Time

Beth Orton

Central Reservation

Arista
via past experience library: 10/26/2003 (TK)

Notes
I See a Darkness

Bonnie ‘Prince’ Billy

I See a Darkness

Drag City
via retroactive experience library: 4/28/2012

Notes
Ohio

Damien Jurado

Rehearsals for Departure

Sub Pop
via the CocoRosie cover by way of Meaghan Massoth library: 1/5/2009

Notes
When You Wake Up Feeling Old

Wilco

Summerteeth

Reprise
via past experience library: 6/14/2004

Notes
Underwater Life

Freedy Johnston

Blue Days Black Nights

Elektra
via past experience library: 11/12/2003 (TK)

Notes
Last Kiss

Pearl Jam

Last Kiss

Epic
via past experience library: 11/11/2003 (TK)

Notes