Every #1 Song of 1998
Pop Princesses, Power Ballads & Peak TRL Energy
In 1998, Gen X was in its late 20s or early 30s, balancing adulthood with an ironic disdain for it. We were still buying CDs at Sam Goody, downloading Winamp skins, and watching Carson Daly crown the latest video gods on TRL.
This year’s #1s were an emotional mixtape—from heartache-heavy duets to high-gloss pop explosions that previewed the bubblegum boom of 1999. Let’s relive the songs that defined 1998 and smacked us right in the mixtape.
📅 January 3 – January 17
“Something About the Way You Look Tonight / Candle in the Wind 1997” – Elton John
Genre: Pop Ballad / Tribute
This one carried over from 1997 and still had the world in its emotional grip. It was global grief wrapped in timeless melody.
🕯️ Gen X Feeling: Still crying. Still playing it on loop.
📅 January 17 – February 13
“Together Again” – Janet Jackson
Genre: Dance Pop / Celebration of Life
Janet came through with a bright, upbeat tribute to friends lost to AIDS. It was both heartbreaking and uplifting—a dance floor elegy we didn’t know we needed.
💃 Gen X Mood: Healing, grooving, remembering.
📅 February 14 – April 3
“My Heart Will Go On” – Celine Dion
Genre: Titanic-Sized Ballad / Eternal
Celine made us all feel like we were floating on a door in the Atlantic. If you didn’t cry during the key change, check your pulse.
🚢 Gen X Moment: Tissues. Goosebumps. Leonardo DiCaprio fan shrines.
📅 April 4 – May 22
“All My Life” – K-Ci & JoJo
Genre: R&B / Wedding Anthem
A slow jam that launched a thousand awkward prom slow dances. This was the love song every couple had to claim as “our song.”
💌 Gen X Core Memory: Practicing the lyrics just in case your crush noticed you.
📅 May 23 – July 17
“Too Close” – Next
Genre: R&B / Club Confession
The catchiest song about dancing a little too close. You sang it out loud before realizing what it was actually about—and then sang it louder.
👀 Gen X Reaction: “Wait… this song is about what?” Then: singing it anyway.
📅 July 18 – August 28
“The Boy Is Mine” – Brandy & Monica
Genre: R&B / Iconic Female Duet
The duet showdown of the decade. Brandy and Monica gave us sass, side-eyes, and a song that lived rent-free in our heads all summer.
💅 Gen X Drama: Picking a side was a thing. (Monica, obviously.)
📅 August 29 – October 2
“I Don’t Want to Miss a Thing” – Aerosmith
Genre: Rock Ballad / Space-Sized Feelings
From the Armageddon soundtrack came this power ballad that sounded like Steven Tyler was trying to stop the asteroid himself. It was loud, emotional, and… everywhere.
🌌 Gen X Popcorn Moment: Saving the world never sounded so dramatic.
📅 October 3 – October 9
“The First Night” – Monica
Genre: R&B / Girl Boss Energy
Monica went solo with a track about setting boundaries—and it still slapped. Catchy, confident, and way ahead of its time.
💋 Gen X Energy: Respect yourself and still make it sound good.
📅 October 10 – November 20
“One Week” – Barenaked Ladies
Genre: Alt-Rock / Stream-of-Consciousness
One week of lyrical chaos. It was quirky, wordy, and totally irresistible. We didn’t know half the lyrics, but that didn’t stop us from trying.
🍜 Gen X Reality: “Chickity China the Chinese chicken…” Nailed it.
📅 November 21 – December 4
“Doo Wop (That Thing)” – Lauryn Hill
Genre: Neo-Soul / Hip-Hop Wisdom
Lauryn came in hot with truth bombs, slick rhymes, and soulful hooks. It was smart, fierce, and had Gen X nodding with pride.
🎤 Gen X Response: Queen. Poet. Legend.
📅 December 5 – December 18
“Lately” – Divine
Genre: R&B / Sweet Slow Jam
One of those quiet hits you forgot you loved until you heard the chorus. A smooth, heartfelt track that was perfect for winter windows-down drives.
🌙 Gen X Thought: Underrated. Still holds up.
📅 December 19 – December 31
“I’m Your Angel” – R. Kelly & Celine Dion
Genre: Pop Ballad / Holiday Weep Fest
Celine returns for the emotional bookend to 1998. This duet was tailor-made for holiday sentimentality, whether or not you asked for it.
🎄 Gen X Summary: We didn’t need another power ballad… but we accepted it anyway.
1998 was the soundtrack to a culture shift. Gen X was growing up—kind of. We were making mix CDs, paying rent, questioning everything, and still showing up for the music. Whether you were vibing with Lauryn Hill’s wisdom or ugly-crying to Celine in your bedroom, one thing was clear:
We felt everything. Loudly. Passionately. And probably with headphones on.