Clockwise from top left: Cher, Madonna, Britney Spears & Backstreet Boys
Clockwise from top left: Cher, Madonna, Britney Spears & Backstreet Boys
Getty Images; Design by Jessica Xie

Here Are 20 Pop Songs That Turn 20 This Year

by Katie Atkinson, Joe Lynch
January 16, 2018, 3:45pm EST

A lot of pop music trends can be traced back to 1998, whether it's boy-band mania proving to be more than just a fluke, the introduction of a pop powerhouse with one breathy "oh baby, baby," or the very early days of an eventual Latin music explosion.

Below, we revisit 20 songs that turn 20 this year. While many are timeless (we're looking at you, "Ray of Light"), plenty were very specifically of this time (we can't imagine "Are You Jimmy Ray?" fitting comfortably on the radio today). So let's take a trip back to 1998, the very same year that MTV's Total Request Live debuted -- and you'll definitely notice some early TRL favorites in the mix.

Britney Spears, "…Baby One More Time"
There are few, if any, debut singles as legendary as this in pop music. And unlike a number of songs from 1998, this one doesn't rely on nostalgia to move the crowd or inspire a sing-along. That winking, dirty piano riff and Britney's defiant, aching delivery ensure that "…Baby One More Time" is an ageless pop classic along the lines of ABBA's "Dancing Queen" -- when it comes on, you're gonna dance. No questions asked.

Cher, "Believe"
Before T-Pain took Auto-Tune to grade school, Cher invited the world to its baptism with "Believe," a mashup of dance-pop and European club music that didn't sound like anything else on the radio in 1998, which is probably why everyone -- from adults who thought of her as a throwback to children who had no idea what a Sonny Bono was -- couldn't get enough of it. It hit No. 1 on the Billboard Hot 100, making Cher the oldest woman to ever top that chart at age 52 -- a record that sadly still holds.

*NSYNC, "Tearin' Up My Heart"
German pop fans knew this song by heart in 1997, but its U.S. introduction came a year later, when it peaked at No. 6 on Billboard's Pop Songs chart, topped the TRL countdown, and coronated *NSYNC as the true rival of the already-established Backstreet Boys, not just another wannabe (of which there were plenty). Speaking of BSB…

Backstreet Boys, "Everybody (Backstreet's Back)"
Backstreet's back -- wait, back from what, you might ask? This oddly titled song was included on the reissue of Backstreet's debut U.S. album, but it was announcing their return to European fans, who had been onboard with the Florida fivesome since 1996. But American fans didn't care: The song went top five on the Hot 100 and girls everywhere positively lost their minds when Nick Carter asked, "Am I sexual?" Yes, apparently you are, Nick.

Madonna, "Ray of Light"
As with "Like a Prayer" a decade prior, "Ray of Light" is as close as dance music gets to religious ecstasy. From the boundless, elastic energy of William Orbit's unstoppable synths to Madonna's orgiastic-yet-Zen vocal climax at the end, "Ray of Light" sounds as fresh now as it did when it helped bring the sounds of the techno underground to the top 40. For bonus transcendence, check out a few of the 10-minute-plus remixes, custom-made for early a.m. jogging.

Brandy & Monica, "The Boy Is Mine"
As the lead single from both Brandy and Monica's second albums and a quasi-sequel to Michael Jackson and Paul McCartney's "The Girl Is Mine," the stakes were high for "The Boy Is Mine." Miraculously, this duet from two nascent talents easily one-upped the original from the two pop titans. From clubs to playgrounds to weddings, "The Boy Is Mine" was an instant classic and inescapable pop culture phenomenon. Credit the divas, who showed simmering restraint always resonates more with listeners than an all-out vocal belt-fest. And the song itself is a brilliant study in contrast, with heavenly harp plucking, a swampy bass line and Rodney Jerkins' James Bond-esque string arrangement demonstrating that disparate sounds are sometimes the best bedfellows.

Fatboy Slim, "The Rockafeller Skank"
On paper, a song that combines countrified guitar twang (via Duane Eddy), old-school hip-hop (via that Lord Finesse vocal sample) and '60s minimalism (think Steve Reich's "It's Gonna Rain") should not equal a pop hit. And yet, the big beat DJ/producer managed to get "The Rockafeller Skank" on the Hot 100. Sure, it peaked at No. 76, but that was enough for pop culture to take notice. From movie trailer commercials to video games to She's All That, the song has never quite gone away.

Ricky Martin, "The Cup of Life"
Of course, 1999's "La Vida Loca" was Ricky Martin's true breakthrough hit, but 1998's frantically paced "The Cup of Life" helped kick-start the late '90s Latin music craze as the official song of the 1998 FIFA World Cup. After that introduction on the world stage, Martin brought the bilingual hit to the 1999 Grammys stage for a hip-shaking performance, and the rest is historia.

Edwin McCain, "I'll Be"
Today, this song is best known as a favorite cover choice on singing competition shows. But back in 1998, the song perfectly soundtracked Joey Potter (Katie Holmes) furiously rowing her way to her one true love in the season 1 Dawson's Creek finale -- only to find Dawson (James Van Der Beek) in bed with Jen (Michelle Williams). Edwin's pleading lyrics ("Tell me that we belong together!") let us feel the pain behind Joey's crooked smile. A simpler time in Capeside.

The Brian Setzer Orchestra, "Jump Jive an' Wail"
This is a 1998 song that feels very long ago indeed. Who would think that after spending the '80s mining rockabilly with the Stray Cats, Brian Setzer would reach even further back in time and successfully revive an even more forgotten subgenre? And yet, the Brian Setzer Orchestra managed to pump life back into swing and jump blues in the '90s, and captured a huge cross-generational fan base in the process. How did it happen? Look no further than the Brian Setzer Orchestra's restless cover of Louis Prima's 1956 classic "Jump Jive an' Wail." The dexterous bass, the bouncing horns and the rapid-fire vocals are enough to wake the dead -- or, in this case, a dead genre -- and make 'em boogie.

B*Witched, "C'est La Vie"
Following in the footsteps of the Spice Girls and paving the way for the bubbly Disney Channel pop-rock of the early '00s, B*Witched deserve a slightly better reputation than what they're left with in 2018. "C'est La Vie" is one of the best girl group songs of all time, and it includes an Irish jig breakdown. Blimey, how many of your favorite pop songs include an Irish jig breakdown? Exactly.

Mariah Carey & Whitney Houston, "When You Believe"
How do you get Mariah Carey to sing for a middling children's movie? G-O-D. Well before contributing to 2017's animated nativity tale The Star, Mimi teamed up with Whitney Houston for another religious kids movie that got mixed reviews, The Prince of Egypt. That flick might not be in the '90s Kids Canon, but at least it afforded us the opportunity to hear two once-in-a-generation voices blend their pipes together for nearly five minutes. And perhaps in a nod to the whole biblical humility thing, neither diva tried to one-up the other: Instead, they focused on selling the simple beauty of the song's melody. And considering it won a best original song Oscar, it seems to have worked.

Celine Dion & R. Kelly, "I'm Your Angel"
Ah, 1998. A point in time when Celine Dion singing with R. Kelly seemed like one of the most innocuous pairings imaginable. Not to mention profitable: Teaming the "I Believe I Can Fly" crooner with the voice of "My Heart Will Go On" assuredly netted some record exec a hefty bonus. Naturally, the duet sailed to No. 1 on the Hot 100. Songcraft-wise, there's not much here worth revisiting, but you gotta give it up for the effortlessly velvety vocals.

Jennifer Paige, "Crush"
Most pop lyrics can be traced back to a puppy-love crush, and this undeniable No. 3 Hot 100 hit puts the simple concept right there in the title. But while plenty of songwriters take a crush far too seriously, this one is perfectly casual. "All I can commit to is 'maybe,'" Jennifer Paige breathily sings. And apparently all pop fans could commit to was a single song from this one-hit wonder.

98 Degrees, "Because of You"
After Backstreet Boys and then *NSYNC established that boy bands were officially back, 98 Degrees were the next ones through the door. The Lachey-bro-led foursome had the harmonies, the looks and the sugary sweet lyrics that made them instant TRL favorites. Please watch the "Because of You" video and remember that these dudes filmed a scene on top of the Golden Gate Bridge -- and it's all because of you.

Jimmy Ray, "Are You Jimmy Ray?"
"Are You Jimmy Ray?" is, without a doubt, one of the weirder one-hit wonders of the '90s -- which is saying something, considering the decade's often-schizophrenic pop music. This British rockabilly guy came out of nowhere with a song about people mixing up his (very simple) name, and people loved it. Never forget that this oddity was a No. 13 hit on the Hot 100 -- and that his name is not Sting Ray, you idiot.

Stardust, "Music Sounds Better With You"
Daft Punk's "Around the World" arrived a year earlier, setting the stage for this other Thomas Bangalter dance project, but this time, he opted for silver body paint instead of a robot head. This is a modern French disco classic, and its Chaka Khan sample and repetitive lyrics make it instantly recognizable.

Shania Twain, "You're Still the One"
Of the 16 songs on Shania Twain's blockbuster Come on Over album, a stunning 12 were released as singles. Let that sink in. Only one, however, remains her biggest hit to date: "You're Still the One," which peaked at No. 2 on the Hot 100 and can still be heard at weddings worldwide. Look how far it's come.

Sarah McLachlan, "Angel"
First of all, picture a time when this song didn't instantly make you think of neglected and abused animals, thanks to Sarah McLachlan's partnership with the ASPCA. Of course, the song's origin isn't any rosier: The Lilith Fair founder wrote it about the heroin overdose death of Smashing Pumpkins touring musician Jonathan Melvoin. This song and its success embody a much more emotional time in music, when a song that would fit in at a funeral was also getting massive radio airplay.

Sheryl Crow, "My Favorite Mistake"
The '90s counterpart to Carly Simon's "You're So Vain," Sheryl Crow's "My Favorite Mistake" attracted a lot of attention given that she all but admitted it was a diss track aimed at a famous former flame. Speculation was endless and helped the bluesy pop-rock tune remain a consistent presence on pop, modern rock and adult contemporary stations. It hasn't gone down in history as one of her best-remembered songs, but it exemplified her ability to thrive on different radio formats with the same tune.