Playlist: 20 songs from the year 2000 that still hold up

As we officially enter the age of nostalgia for Y2K, a selection of songs from that era that don’t sound their age

Since 2011, I’ve been putting together an playlist of my favourite songs from the past year and sharing it here on my blog. I’ll be posting my 2019 list soon, but before that happens I want to do something I haven’t before and travel back in time to a previous era.

It’s 2020 now which means the year 2000 has officially entered the age of nostalgia: as Emily Guskin pointed out on Twitter, if the Wonder Years were to come out now, it would cover the years 2000 to 2005.

This just so happens to mark the era of my musical awakening: from the ages of 15 to 20, I voraciously consumed all genres of music, old and new, as the advent of Napster, Limewire and my own CD burner gave me access to pretty much anything I could imagine, and Columbia House allowed me to get my favourites perfectly legally for a decent monthly fee.

The songs on this list aren’t necessarily the ones I listened to the most in my fifteenth year on earth– in fact, some I wouldn’t discover until later– but they are the ones that still sound good to my 34-year-old ears (January baby), and whose existence helped shape the way I would think about music for the next two decades. Enjoy.

Track One: Alliyah, “Try Again”

Doing this in chronological order, we have to start with the lead single from “Romeo Must Die”, Aaliyah’s “Try Again” released Feb. 22. A staple of my friend’s basement Napster playlist for the year and my intro to Timbaland.

Track Two: Kid Koala, “Fender Bender”

Also from February, it’s “Fender Bender” from Vancouver’s Kid Koala. I distinctly remember seeing this on MuchMusic and being blown away that this was all done using samples!? “You got another one of those crazy sound effect records you wanna show off?”

Track Three: Dead Prez, “Hip Hop”

“One thing ’bout music when it hit you feel no pain” And thus opened one of the greatest hip-hop songs of all time.

Track Four: The Hives, “Hate To Say I Told You So”

This was originally released in May 2000, though I’m sure I didn’t hear it until later. But when I did, it hit hard– one of the first songs I learned to play on guitar and one of my ways into rock as a tight mess.

Track Five: Modest Mouse, “Paper Thin Walls”

I definitely didn’t hear this for a couple more years, but I have to include it here in part because when I got my first cellphone (a candybar Nokia) it was one of my first custom cellphone ringtones.

Track Six: Janet Jackson, “Doesn’t Really Matter”

The “EDIT” breakdown at 1:57 on this dates things a little bit, but honestly, this track– from the “Nutty Professor II: The Klumps” OST of all things– still holds up as an R&B/pop song.

Track Seven: Nelly, “Country Grammar (Hot Shit)”

I thought for sure that Nelly’s debut single would sound dated, hopelessly latched to the production styles of 20 years ago. But it doesn’t. This could be released today and still hit the same way.

Track Eight: The White Stripes, “You’re Pretty Good Looking (For a Girl)”

I wouldn’t find the White Stripes until that crazy Lego music video for “Fell In Love With A Girl” came out a couple years later, but once it did I went back to listen to everything else they’d done. This is the highlight of their pre-MTV years.

Track Nine: Coldplay, “Yellow”

Forget the Super Bowl. Forget “Conscious Uncoupling”. Forget every bland arena anthem that’s come since. Put this on a mixtape and listen to it in the dark with your eyes closed. Love it like you did when it first came out. It’s worth it.

Track Ten: Dr. Dre feat. Snoop Dogg, “The Next Episode”

2000 was the year of the Marshall Matthers LP– “The Real Slim Shady,” “The Way I Am,” “Stan.” It defined the era. But to my ear, this mid-summer single from Eminem’s forbears sounds far more timeless. And dozens of teenagers TikToks agree.

Track Eleven: Robbie Williams, “Rock DJ”

Time for another hop across the pond. I also didn’t expect this to hold up. But it absolutely does.

Track Twelve: Madonna, “Music”

2000 was the pinnacle of the teen pop era. N*Sync dropped “Bye Bye Bye”, Britney had “Oops… I Did It Again” and Backstreet Boys were still going strong. But the absolute best pop song of the year came from an icon entering her 40s with Ali G at the wheel.

Track Thirteen: Destiny’s Child, “Independent Women, Pt. 1”

Like Janet Jackson’s track earlier in this list, “Independent Women” from Destiny’s Child is awkwardly tied to a movie soundtrack, even in the lyrics. But the production, the delivery, absolutely overcomes it and belongs alongside Beyoncé’s greatest hits.

Track Fourteen: Radiohead, “Everything In Its Right Place”

OK, summer’s over. Fall is arriving. And we are about to hear the most mind-blowing, weirdest turn for a rock band– maybe ever? It’s time for Radiohead’s Kid A and “Everything In Its Right Place”.

Track Fifteen: U2, “Beautiful Day”

2000 had a lot of artists who could’ve just rested on their laurels doing the work to actually make good music. Anyways, this went on to be a post-9/11 anthem, but it belongs in the year 2000, and all the optimism of that era that was about to be broken.

Track Sixteen: Outkast, “Ms. Jackson”

A love song, a diss track, a club jam, a campfire singalong. From hip hop’s answer to “Kid A” and arguably the greatest record of the next 20 years. It’s Outkast with “Ms. Jackson.”

Track Seventeen: Sade, “By Your Side”

Released in October in the UK, “By Your Side” by Sade didn’t get its proper North American debut until early 2001. But it’s gone on to be an absolutely timeless love song– one that it’s impossible to cover badly, but also impossible to top the original.

Track Eighteen: The New Pornographers, “Slow Descent Into Alcoholism”

It would be a few years before Canadian indie broke big with the rise of Arcade Fire, Feist, and Broken Social Scene. But the first volley from the Great White North was fired with the New Pornographer’s Mass Romantic. Shoutout to MuchMusic’s “The Wedge”.

Track Nineteen: The Avalanches, “Since I Left You”

If Kid Koala blew my mind with what could be done with record samples in February, by November it was about to be blown apart with the Avalanches and their album “Since I Left You.” The title track sounds like it was released yesterday.

Track Twenty: Daft Punk, “One More Time”

And finally, on November 30, 2000, a pair of French robots sang into 2001 and the new millennium. The past was over. The future was here. Don’t stop the dancing.