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The 98 Best Songs of 1998: Pop’s Weirdest Year

In 1998, boundaries blew open and new genres were invented each week. We look back at the best, brightest and weirdest from a pivotal year in pop

The Top 98 Songs Of 1998: The Weirdest Pop Year Ever

Rob Sheffield counts down the greatest songs of 1998, pop's weirdest year – from Foo Fighters to Fatboy Slim.

The year 1998 had some great ideas our culture gave up on too soon: Internet cafes, travel agencies, Jennifer Love Hewitt’s singing career. Plus questionable ideas, like Canadians rapping about Chickity China the Chinese Chicken. But most of all, it was a year full of music. Every genre was booming – rap, modern rock, electronica, R&B divas, Britpop poseurs, indie slop, trip-hop, coffee-house techno, wherever the hell you’d file “The Rockafeller Skank.” The music world kept changing so fast, songs could explode out of nowhere to become huge hits, in a way that was unthinkable just a couple of years later. Fans bought CDs (with money!) at a record-breaking rate. One-hit wonders flourished. Legendary veterans changed their games. Beyoncé was just the second girl from the left in a new group called Destiny’s Child. The sky was the limit, right before Napster arrived and the boom went bust.

So let’s break it down: the 98 greatest songs of 1998, 20 years later. The hits, the flops, the total obscurities, the cult classics. The guitar monsters, the rap bangers, the rump shakers, the soul jams. A personal, opinionated, subjective, irresponsible and indefensible celebration of the weirdest pop year ever. Some of these songs came from all-time classic artists, others from brazen one-shots; some were so bizarre or obscure that airplay was out of the question. But they all sum up the anything-goes spirit of 1998, a moment when stylistic boundaries blew wide open. These songs helped invent the future we’re living in today.

It was a time of historic transformations. Nobody knew teen-pop and nu-metal and MP3s and Google were right around the corner. Sinatra and Seinfeld signed off the same night. MTV debuted Total Request Live. George Michael came out. Kurt, Biggie and Tupac were dead, yet their legacies helped inspire a creative boom for both rappers and rockers. The New Radicals showed up sounding just like Hall & Oates. Hall & Oates came back sounding just like Hall & Oates. (And damn straight, both made this list.) New genres got invented every week, which was how long most of them lasted. But these faves are just the tip of the iceberg – the full list could stretch into quadruple digits easily. As for what counts as a 1998 song, there’s a lot of grey area – if a song made its impact in 1998, it’s fair game even if it had an official 1997 release date. On the other hand, many greats technically came out in late 1998, but didn’t made their real impact until later. (Just to pick the most obvious example, Britney’s “Baby One More Time” appeared at the end of the year, but it spiritually belongs to 1999, when it changed the world.)

Stakes were high, for the simple reason that we all loved music so fiercely. Fans went to the record store, chose CDs off the racks, took them home, cranked them all night. We had no trouble finding songs to love, to argue about, to put on mixtapes and pass around. You can hear that excitement right in the music, which is why all 98 of these songs still sound so brilliant today. So let’s celebrate the best of 1998. As Garbage sang that summer: Push it. Make the beats go harder.

Best songs of 1998 watch read listen
32

Monica, “The First Night”

Although dueling teen divas Monica and Brandy spent the summer at Number One with their claws-out duet “The Boy Is Mine,” they scored much livelier hits on their own. In “The First Night,” Atlanta girl Monica dishes about her sexual prerogatives – “I wanna get down, but not the first night” – over a filthy disco bass thump sampled from Diana Ross’ “Love Hangover,” via her producer Jermaine Dupri. It wasn’t the easiest year to be a one-named celebrity called “Monica” – the headlines were full of a certain stained blue dress – but she rode “The First Night” to Number One for five weeks. Monica went on to star in the BET reality show Monica: Still Standing and married NBA star Shannon Brown.

Best songs of 1998 watch read listen
31

Silver Jews, “The Wild Kindness”

“I’m perfect in an empty room,” indeed.
Even longtime Silver Jews fans got our juleps spilled by the greatness of American
Water
– David Berman’s ultimate testament as a poet, crooner and prankster,
the kind of genius that could only flourish in bourbon-drenched slack-ass Southern
boho towns. Pavement’s Stephen Malkmus plays the madcap sidekick on guitar and
back-up vocals, the Ghostface to Berman’s Raekwon. It’s torture to pick just
one highlight from such a flawless album – the universally beloved saloon
ballad “Random Rules?” The ramshackle Al Green/Willie Mitchell jam
“Blue Arrangements”? The stupidly titled “Like like the the the
Death”? But “The Wild Kindness” makes a fittingly ceremonious
finale, as Berman gets somber in his Leonard Cohen mode (“It is autumn and
my camouflage is dying”) and Malkmus plays that bottomlessly sad guitar
solo.

Best songs of 1998 watch read listen
30

Massive Attack, “Angel”

The Bristol crew that invented trip-hop – Daddy 3,
Mushroom and 3-D – got even heavier on Mezzanine. While everybody else
was still racing to catch up with what Massive Attack were doing in 1994 on Protection,
these guys swerved into the unknown – anyone who could turn the Cocteau Twins’
Elizabeth Fraser into a soul singer (as in “Teardrop”) was definitely
on some new shit. “Angel” remains their most enormous track ever, a
six-minute descent into the abyss, with reggae stalwart Horace Andy pleading
for mercy over ominous bass, an “Apache” beat that rumbles like John
Bonham getting crushed under broken levees, cinematic strings and blasts of
Hendrix-gone-Kingston guitar.

Best songs of 1998 watch read listen
29

Prince and the New Power Generation, “Mad Sex”

Prince was in semi-retreat in the late 1990s, hiding behind the identity of his back-up band, the New Power Generation – yet still sounding unmistakably like himself. “Mad Sex” is a hidden jewel from the totally slept-on NPG album Newpower Soul; Prince vamps with jazz piano and trumpet while he chases a wet-lipped London party girl, as they dirty up another room. “Mad Sex” comes on like an updated “Lady Cab Driver” with the Purple One’s take on Nineties fashion: “Do it till your tattoo’s dizzy/And the stud in your mouth turns gold/Till the animal prints you flaunt so lovely/Is full of little bloody holes.”