Following our Billboard staff-picked list of the 99 greatest songs of 1999, we’re writing this week about some of the stories and trends that defined the year for us. Here, we look back at lyrical moments that reflected the classic era in a way that only made sense at the time.
Each decade in music serves as a historical snapshot of what made that era so special: the presidents that got elected, the impressive strides in science & technology and the ever-changing trends in fashion. And in the ’90s — and with the end of the century looming, 1999 specifically — many artists used their songs to capture timely pop culture moments.
Some opted to reference celebrity figures (we’re looking at you, Eminem) and others used impending Y2K Scare as inspiration for transitioning into the high-tech New Millennium. While it appeared cool to ramble on about DVDs and emails at the time, a lot of these references didn’t age well — but we still love them anyway!
Below, we’ve rounded up the 13 best lyrics from that beloved year, which range from clever to corny.
1. Britney Spears, “E- mail My Heart” (…Baby One More Time)
“E-mail my heart and say our love will never die / And that I know you’re out there and I know that you still care / E-mail me back and say our love will stay alive / Forever, E-mail my heart”
If you can believe it, emailing was a new concept in 1999. Long before it was possible to slide in your crush’s DMs, actually turning on your desktop to type out an e-mail was one of the few ways to contact people. Britney Spears turned it into a sappy ballad for her …Baby One More Time debut, begging her boyfriend to answer her pleas. The theme surely didn’t age well, but at least it blessed us with this iconic gif.
2. TLC, “FanMail” (FanMail)
“Said I got an email today/ Kinda thought that you forgot about me/ So I wanna hit you back to say/ Just like you, I get lonely”
The newly-defined online culture carried throughout 1999, with TLC using technology as inspiration for its third album FanMail. The combination of female android Vic-E along with these chilling lyrics created a feeling of disconnection that somehow emotionally registered beyond the computer screen.
3. Blackstreet, “Girlfriend/Boyfriend” (Finally)
“Blowin’ up my pager cuz he ready to bone/ Played me once, won’t leave me alone”
If the incessant FaceTime calls we get from pursuiters weren’t annoying enough, just imagine what the generation before us had to deal with. The idea of a pager ringing non-stop because someone is trying to schedule a booty call seems like a headache.
4. Mobb Deep featuring Lil Kim, “Quiet Storm” Remix (Murda Muzik)
“Keep my Dunns close to me, enemies even closer/ Sendin’ kites with the Motorolas, yo”
Can you imagine a life without your beloved iPhone? Well in 1999, folks had to rely on flip phones for communication. But rather than making standard calls, Mobb Deep hinted at using the bulky Motorolas to send messages in prison.
5. Blaque, “Bring It All To Me” (Blaque)
“Are you feeling my Timb’s, my baggy jeans?/ My thug appeal?”
Blaque’s cutesy collaboration with JC Chasez birthed one of the best lyrical moments that diehard *NSYNC still can’t get over 20 years later. Back then, the boy band singer’s vocals was filled with so much swagger that almost made you believe he could rock Timb’s with ease. But let’s be real here. As much as many of us would like to believe it, JC didn’t hold one ounce of thug appeal.
6. Destiny’s Child, “Bug A Boo” (The Writing’s on the Wall)
“You make me wanna throw my pager out the window/ Tell MCI to cut the phone calls/ Break my lease so I can move/ Cause you a bug a boo, a bug a boo/ I wanna put your number on the call block/ Have AOL make my emails stop/ Cause you a bug a boo”
No one likes a pestering bug-a-boo, and the ladies of Destiny’s Child made it known on this classic kiss-off anthem. Before the concept of “curving” became popular, they relied on now-outdated technology like pagers, emails and landline phones to threaten men to leave them the heck alone.
7. Eminem, “If I Had” (The Slim Shady LP)
“Tired of wearin’ the same damn Nike Air hat/ Tired of steppin’ in clubs, wearin’ the same pair of Lugz”
Do people even wear Lugz anymore? They may be out of style now, but back in 1999 the urban fashion brand was worn by the likes of Dr. Dre and Notorious B.I.G. Just don’t get caught rocking a pair now…
8. TLC, “No Scrubs” (FanMail)
“A scrub is a guy that thinks he’s fly/ He’s also known as a busta/ Always talkin’ about what he wants/ And just sits on his broke ass”
The male sex has been riddled with bad seeds since the beginning of time. And before they were known as “fuckboys,” the year 1999 had a different label for them. The idea of a “scrub” was created by songwriter Kandi Burruss, who used the term for wack dudes. Compared to 2019, ‘90s slang seemed to be more forgiving when it came to branding no-good men with nicknames.
9. Sporty Thievz, “No Pigeons” (Street Cinema)
“You birds wanna take over?/ Get some cash and a Jenny Jones makeover/ broke bitches, I hate pigeons”
Aside from being a funny response to TLC’s anthem, Sporty Thievz managed to date their parody song with two references that barely hid the song’s age. The Jenny Jones Show was a huge ‘90s tabloid talk show that featured paternity tests and unruly teenagers, while the “pigeons” slang never made it past Y2K.
10. LFO, “Summer Girls” (LFO)
“I like girls that wear Abercrombie and Fitch/ I’d take her if I had one wish/ But she’s been gone since that summer, since that summer”
LFO’s catchy debut single “Summer Girls” is chockful of pop culture references from various decades, from New Kids on the Block to Paul Revere and Home Alone. But the boy band’s call-out to fashion brand Abercrombie & Fitch reflected the suburban style of ‘99.
11. Will Smith, “Will 2K” (Willennium)
“Now it’s 9-9, ten years behind me/ What’s gonna happen?/ Don’t nobody know/ We’ll see when the clock gets to 12-0-0/ Chaos, the cops gonna block the street”
Remember when everyone thought the world was going to come crashing down in the new millennium? In true Will Smith fashion, the rapper/actor transformed that fear of androids taking over the world by creating a silly party anthem that you could jam to before the ball dropped. Luckily we survived long past the year 2000, but this song could’ve stayed behind.
12. Blessid Union of Souls, “Hey Leonardo (She Likes Me for Me)” (Walking Off the Buzz)
“I like her for her/ Not because she’s phat like Cindy Crawford”
“Hey Leonardo (She Likes Me for Me)” is one of Blessid Union of Souls’ most popular songs — which is most likely due to its impressive number of late ‘90s references. The alternative rock bands show love to DVDs, Tyson Beckford (one of the decade’s famous male models), Jim Carrey (and The Cable Guy), Fargo. But the most ‘90s-leaning moment is the smooth use of “phat.”
13. B.G. feat. Baby, Turk, Mannie Fresh, Juvenile & Lil Wayne, “Bling Bling” (Chopper City in the Ghetto)
“Bling bling, every time I come around your city/ Bling bling, pinky ring worth about fifty”
Before Nelly wanted to show off his grillz and Migos were flashing their Patek watches, the Hot Boys were all about their bling bling. It’s unclear if Lil Wayne was actually the one to invent the slang term, but he definitely popularized it on this track — and his counterparts agreed. Like Lil Turk of the Hot Boys exclaimed: “1999, and it’s our turn to shine!