Why 1998 Was the Best Year in Music for Millennials: Jay-Z, Britney Spears, More

Boasting an eclectic array of hits, from boy bands to rap, why 1998 was the best year in music for millennials.

It was the best of times. It was an age of prosperity, with six years in a row of fiscal improvement under the leadership of President Bill Clinton—including the first U.S. budget surplus in 30 years. Gas cost just $1.15 a gallon. It was an epoch of innovation, with the founding of Google, the rise of e-commerce, and the FDA’s approval of Viagra to treat erectile dysfunction. The N.S.A wasn’t tracking every phone call you made and hackneyed inspirational quote you posted to Facebook (which did not yet exist). In short, the period was so unlike the present one.

I’m talking about 1998.

That halcyon year was also a great one for music—and the last before the file-sharing site Napster was introduced, upending the record industry. In fact, George Michael’s bathroom snafu notwithstanding, 1998 was, without question, the best year in music for millennials.

Here’s why.


Back in 1998, Jay-Z was a 27-year-old up-and-coming rapper with two albums under his belt—Reasonable Doubt and In My Lifetime, Vol. 1. The latter managed to achieve platinum status, despite mixed reviews from critics that took aim at its glossy production, courtesy of Puff Daddy’s Bad Boy label. But it was his album released in ‘98, Vol. 2… Hard Knock Life, which propelled Jay-Z to superstar status. He got rid of the Bad Boy producers, replacing them with up-and-coming beatmakers such as Swizz Beatz, Timbaland, and Jermaine Dupri, to create a crossover album that mixed gritty tracks from Swizz with radio-friendly jams, including the “Annie” theme-sampling “Hard Knock Life (Ghetto Anthem),” and “Can I Get A…” The album was Jay-Z’s first to debut at No. 1 on the Billboard charts—and the first of nine chart-topping LPs—selling over five million copies, and later won the Grammy for Best Rap Album. With Biggie gone, someone had to take his place as the king of East Coast rap, and in 1998, Jay-Z did. That same year, the self-titled debut album by Destiny’s Child was released. The debut effort by the R&B girl group, led by Beyoncé Knowles, was a hit, selling over three million copies worldwide, thanks in large part to the success of single “No, No, No.” Jay-Z and Beyoncé met the following year, and the rest is history.


In addition to Destiny’s Child, we were introduced to a ton of (now big) artists that released their first material in 1998. In the interest of brevity, here’s a list: Boards of Canada, Air, Dixie Chicks, Queens of the Stone Age, Gomez, Mya, Big Pun, DMX, Rufus Wainwright, Black Eyed Peas, Godspeed You! Black Emperor, System of a Down, Cam’ron, Death Cab For Cutie, Lauryn Hill (solo debut), Black Star, Jurassic 5, and Canibus. Also, the first EPs were released by a couple of now-household names: Coldplay and Muse.


On Sept. 14, 1998, back when MTV still played music videos, Total Request Live—or TRL—aired for the first time. Hosted by Carson Daly, the after-school music video countdown show would soon become MTV’s flagship program, and for the next decade, played a huge role in influencing the musical tastes of countless tweens, and helped launch the careers of countless boy bands and pop princesses (see below).


Thanks in part to Total Request Live, pop music really soared in 1998. We were introduced to the boy band ‘N Sync, led by Justin Timberlake, who released that self-titled debut album that year, including the hit songs “Tearin’ Up My Heart” and “I Want You Back.” Their boy band rival, Backstreet Boys, released their hit single “Everybody (Backstreet’s Back),” while a little-known pop singer by the name of Britney Spears released her first single, “…Baby One More Time.” Also, Aaliyah released the single to the Timbaland-produced “Are You That Somebody?”, which is arguably her best song. The veterans got in on the act, too. Madonna’s dance-y comeback album of sorts, Ray of Light, was released, which went on to sell over 16 million copies worldwide and win a number of Grammys, and Cher’s comeback effort, Believe, also hit record store shelves, and would eventually move over 20 million units.

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In addition to all the debuts, and Jay-Z’s crossover album, there were a slew of fantastic albums from established artists released in that fateful year. Fatboy Slim’s You’ve Come A Long Way, Baby, which included the songs “The Rockafeller Skank” and “Praise You,” is now regarded as a dance classic. The Beastie Boys added Mix Master Mike to their lineup and released their Grammy-winning fifth album Hello Nasty, which included the hit single “Intergalactic.” Former Fugees member Lauryn Hill released her solo debut, The Miseducation of Lauryn Hill, which remains one of the greatest R&B albums ever. There were stellar albums released in a variety of genres, including rap (Gang Starr’s Moment of Truth, Outkast’s Aquemini, Goodie Mob’s Still Standing), indie (Pulp’s This is Hardcore, Beck’s Mutations, Sonic Youth’s A Thousand Leaves, Belle & Sebastian’s The Boy with the Arab Strap), and rock (Garbage’s Version 2.0, Hole’s Celebrity Skin, and Billy Bragg and Wilco’s Mermaid Avenue, wherein they performed unreleased Woody Guthrie songs). Also, we were introduced to Snoop Dogg—previously Snoop Doggy Dogg—who released his first album after leaving Death Row Records: Da Game Is to Be Sold, Not to Be Told.


The sophomore album by Neutral Milk Hotel, a lo-fi indie rock band led by singer-songwriter Jeff Mangum, was released in 1998 and remains one of the best albums ever. In the Aeroplane Over the Sea was inspired by Anne Frank’s The Diary of A Young Girl, and paints an arresting portrait of an alternate universe where Frank is alive, and acting out Where the Wild Things Are-type fantasies. “And here’s where your mother sleeps / And here is the room where your brothers were born / Indentions in the sheets / Where their bodies once moved but don’t move anymore,” Mangum hauntingly sings. It’s a fascinating concept album that, like a fine wine, only gets better with age.

‘90s Hits

Many of the songs that we consider quintessential ‘90s were released in ’98. Here’s a few:

Aerosmith – “I Don’t Want To Miss A Thing”

--The first No. 1 hit ever for Aerosmith, from the soundtrack to the blockbuster film Armageddon. It’s now a slow-dance staple at weddings.

Fastball – “The Way”

--An infectious alt-rock tune about an older couple who pack up all their belongings and embark on an epic road trip, finding happiness along the way.

Semisonic – “Closing Time”

--This song, about the anticipation of fatherhood, appeared on shows like Friends, The Simpsons, The Office, and the final episode of Melrose Place.

Everlast – “What It’s Like”

--A guitar-strummin’ anthem about the less fortunate by the former House of Pain member that focuses on a beggar, a pregnant woman seeking an abortion, and a drug dealer.

Brandy & Monica – “The Boy is Mine”

--The year’s best-selling song features a great vocal interplay between Brandy and Monica, and spent 13 weeks atop the Billboard Hot 100 chart.

Harvey Danger – “Flagpole Sitta”

--GREAT chorus.

Pras feat. Mya and Ol’ Dirty Bastard – “Ghetto Superstar (That Is What You Are)”

--This catchy-as-all-hell R&B tune was school dance staple for millennials, from the soundtrack to the film Bulworth.

Wyclef Jean – “Gone till November”

--Still his best song.

Natalie Imbruglia – “Torn”

--A fantastic pop tune from way back when lots of music videos were shot in apartments.

Big Pun feat. Joe – “Still Not A Player”

--“In the hot tub, poppin’ bubbly…”

Eagle Eye Cherry – “Save Tonight”

--The lead single from the Swedish musician—and son of jazz legend Don Cherry—boasted a truly ridiculous monochrome music video, but is catchy nonetheless.

Barenaked Ladies – “One Week”

--No comment…


In 1997, the website had begun releasing digital MP3 versions of songs by artists, often with their consent. Mezzanine, the third studio album by UK trip-hop collective Massive Attack, is notable for being one of the first albums to be released digitally—and legally—via the band’s website a few months before the CD came out, marking the biggest use to date of MP3’s by a major record label (Virgin Records).