Playlist of the Week: 1999

I learned a fun fact last week. And by “fun fact” I mean I saw about a kajillion stories written about it.

January 12 was the 20th anniversary of the release of Britney Spears’ “Baby One More Time.” We’re all old AF.

Britney is far and away the biggest pop star of the last two decades, and you can’t argue with me otherwise. Alongside Michael Jackson, Janet Jackson and Mariah Carey, she’s probably a top 5 biggest pop star of all time, and 1999 was when we were introduced to her.

The year 1999 was a fun one. All of us millennials will likely remember Britney vs. Christina and BSB vs. N’Sync, but it was also a truly fantastic year for pop outside of the Big 4.

It was also a weird year. Like, Adam Sandler’s “The Chanukah Song” was No. 80 on the Billboard Hot 100 charts ON JANUARY 2. Why?

There were actresses trying to be pop stars, music videos playing during every Disney Channel commercial break, we were introduced to Slim Shady, and all livin’ la vida loca.

That’s why I want to spotlight the turning point in pop with some other lost gems and huge hits that you may have forgotten over the last two decades in this week’s Playlist of the Week.

(PS – the playlist is available on Spotify below. You’re welcome.)

Playlist of the Week: 1999

  • Have You Ever? – Brandy

When you think of Brandy is your first thought of her as a singer or actress? “Moesha” was super popular, and the version of “Cinderella” with her and Whitney Houston is so, so, so good. But Brandy also had huge hits, especially 1998’s “The Boy is Mine.” So it’s a tossup.

When I think of Brandy my first thought is usually remembering she went to prom with Kobe Bryant.

  • Angel Of Mine – Monica
  • Say My Name – Destiny’s Child
  • Are You That Somebody – Aaliyah

  • Take Me There – Blackstreet & Mya

This is from the Rugrats movie!

  • When You Believe – Whitney Houston & Mariah Carey

This is from The Prince of Egypt movie!

Also, remember how everyone thought it was crazy that Mariah and Whitney would do a song together because everyone assumed they hated each other? The 90s were fun because women in the same field could never not be in competition…

  • Angel – Sarah McLachlan

Just kidding, this isn’t on the playlist. You’re thinking of sick dogs now and crying though, aren’t you?

  • Angel of Mine – Monica

Much better song about angels.

  • Heartbreaker – Mariah Carey & Jay-Z
  • Where My Girls At – 702
  • Bring It All To Me – Blaque

  • Miami – Will Smith

Here’s a fun story. My senior year of high school we were sitting in government class and for some reason one guy was going around the room asking everyone who their favorite rapper was. Me being a chorus kid who only listened to 80’s pop, the High School Musical soundtrack and Ben Folds Five, I panicked and had no answer, so I was just like “uh, um, I guess, uh, Will Smith?” And everyone laughed, and I to this day I don’t know if they were laughing at me because I couldn’t name a single other rapper, or they thought I was making a joke. I like to pretend it was the latter.

Also, 20 years later “Miami” is still a banger.

  • Wide Open Spaces – Dixie Chicks

The year 1999 was a BIG year for country/pop crossovers. Also, the Dixie Chicks “Fly” album is still one of the best country albums ever, ever, ever made.

  • That Don’t Impress Me Much – Shania Twain
  • Amazed – Lonestar

  • One Week – Barenaked Ladies

This song came on the radio the other day and before it started the DJ said “the lead singer of the Barenaked Ladies said he was surprised by the commercial success of ‘One Week’ because it was all improvised.” And I was SHOCKED! You’re telling me “Chickity China the Chinese chicken, you have a drumstick and your brain stops tickin’” wasn’t something conceived in a week long writing session with several professional songwriters all giving input? UNBELIEVABLE!

  • You Get What You Give – New Radicals
  • Fly Away – Lenny Kravitz
  • Can’t Get Enough of You Baby – Smash Mouth



  • Candy – Mandy Moore

Remember how every young actress in the late 90s/early 2000s also did music? Next time you’re crying while watching “This Is Us,” just remember this song and it’ll clear them tears right up.

  • How Do I Deal – Jennifer Love Hewitt
  • Waiting For Tonight – Jennifer Lopez

  • I Think I’m In Love – Jessica Simpson

When I was younger I legitimately thought Jessica Simpson had the best voice of anyone on earth. Then, my freshman year of high school I took a creative writing class and the teacher for some reason one day went on this like 20 minute rant about how there was no good music anymore and all female singers are auto-tuned and he said specifically Jessica Simpson actually can’t sing AT ALL, she’s terrible and a disgrace to the music industry.

And yall, I was distraught! It still… I mean… how dare he? Has he never listened to her sing Robbie William’s “Angels” LIVE? You can’t autotune LIVE! (Okay, I think you can, but yall, believe me, DISTRAUGHT!)

Doesn’t matter, Jessica Simpson runs a billion dollar company now.

  • C’est La Vie – B*Witched

How many times did you watch the music video to this on Disney Channel?

  • Slam Dunk (Da Funk) – 5ive

Same question.

  • Kiss Me – Sixpence None the Richer
  • Don’t Say You Love Me – M2M
  • Smile – Vitamin C

  • Summer Girls – LFO

Abercrombie & Fitch would be out of business now if it wasn’t for this song. Tell me I’m wrong.

  • Bring It All Back – S Club 7

Which member of S Club were you?! I was Hannah.

  • No Scrubs – TLC

The song that popularized the word “scrub” in the English language.

  • Too Close – Next
  • All My Life – K-Ci & JoJo
  • Back At One – Brian McKnight


  • We Like to Party – Vengaboys

I did a dance to this song in my fifth grade talent show! I still remember it!

(Also, I realized this a few months ago. The band is called The Vengaboys but every one of their lead singers is a girl ¯\_(ツ)_/¯)

  • Lean On Me – Kirk Franklin

The really cool thing about this song is you could do a really sweet slow dance to it at a middle school dance, and then the next morning sing it in church!

  • I Want It That Way – Backstreet Boys

The year 1999 was truly the year of the boy band. Fun fact – this is widely considered the Backstreet Boys biggest hit, but it actually never got higher than No. 6 on the Billboard Hot 100 charts.

The video, however, was retired on TRL and voted the show’s No. 1 most iconic song of 1999. FOR GOOD REASON!

  • (God Must Have Spent) A Little More Time On You – N’SYNC
  • The Hardest Thing – 98 Degrees
  • Back Here – BBMak

  • Bailamos – Enrique Iglesias

It was also a big year for Latin American artist. RIP Enrique’s mole.

  • Shake Your Bon-Bon – Ricky Martin
  • I Need to Know – Marc Anthony

  • Crush – Dave Matthews Band

I’m putting this on the list because it’s my favorite Dave Matthews song, so there!

  • Why Don’t You Get a Job? – The Offspring
  • Last Kiss – Pearl Jam
  • What’s My Age Again – Blink-182
  • Steal My Sunshine – Len

  • Millennium – Robbie Williams

I weirdly loved this song as a kid. Also, I have no idea why, but I always thought Robbie Williams was the biggest douche, and to this day I still think that but I can’t remember why I thought that, I just think it’s true. I’m pretty sure it’s true, but I don’t feel like Googling to know for sure. Good songwriter though.


  • You’ll Be In My Heart – Phil Collins

The best song from a Disney movie ever, you can’t change my mind.

  • My Name Is – Eminem

Remember when all the PTA Super Moms heard Eminem for the first time and like FREAKED OUT? And then like a few years later he came out with stuff that made “My Name Is” seem like Kidz Bop? He was controversial.

  • What A Girl Wants – Christina Aguilera

I’m not putting “Genie in a Bottle” on this playlist because that song is disgusting. Have you ever really listened to the lyrics? She was only 18. How did that play on Disney Channel???

Plus, this song is just better. Also, I relistened to Christian Aguilera’s debut album a while back because I spend a lot of time in the car and get bored,  and let me just say it holds up. It’s still her best work.

  • Sometimes – Britney Spears

Yea, bet you thought I was gonna put “Baby One More Time” on this playlist too, didn’t ya? Well it’s cliché and frankly I think the “Sometimes” music video is just as iconic. The part where all the dancers are wearing white pants and doing weird arm moves on the pier? You still remember that part. You tried to learn those weird arm moves by rewinding your VHS tape recording of TRL a million times.

Also, you know how Cady Heron wore army pants and flip flops so other girls wore army pants and flip flops? Well in this video Britney wears a long-sleeved white shirt with jean shorts, so the whole summer of 1999 I also wore a long-sleeved white shirt with jean shorts. I-CON-IC.


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