🎶 Five Songs that Catapult Me Back to My Youth

Millennial Music Flashbacks

Apr 17, 2025

Maybe it’s my Type A, slightly obsessive, and a little compulsive personality, but I love matching music to certain aspects of life. A playlist for breakups, a mix tape for middle school, or a burned CD for theatre vibes. Some songs, though, bring me back to a certain space in time. I’ll hear an ever-familiar opening and suddenly I’m a child again, riding across the US East Coast on a family road trip, our family’s Siberian Husky sleeping in the seat next to me, or I’m 19 and sitting in my car, crying into my steering wheel. Here’s a list of only a few songs that take me on these time-traveling trips.

Preteens

“Only in My Dreams” by Debbie Gibson, 1987

(I was 3 years old at release, but 6 and beyond when I was a fan.)

I was in the backseat of my Mom’s white car. I sat leaning against the driver’s side door, gazing out the window and looking into the sky. The trees brushed the sky of the forests as we zoomed over the pavement. A slither of a pale crescent moon was rising above the tree line, their branches reaching up to catch it, and my inquisitive child mind pondered why the moon appeared to be following us on our journey through the German countryside. Over the car’s speakers, my favorite song came on, sung by the only singer I knew who wasn’t a Disney princess.

From Gibson’s debut album, Out of the Blue, of which she wrote and co-produced every song at only 16 years old1, “Only in My Dreams” is fitting for me as a baby Pisces to have been obsessed with from toddlerhood to school age. Debbie Gibson was my favorite pop artist in the younger grades of elementary school, and although I eventually graduated to Madonna, Whitney Houston, and Mariah Carey, Debbie Gibson’s CDs were a pride of my music collection.

“Ironic” by Alanis Morissette, 1995

(I was 11 and felt this album so hard, most of the metaphors flying over my head.)

Jade and I laid on our stomachs, stretched out on the beige carpet of her bedroom, which was light, airy, and floral chic, dressed in all-white furniture and accented with pink and green prints. We scored each other’s MASH sheets2 while listening to New Jersey’s local Top 40 station. Alanis Morissette, a new-to-us singer who added some edge to our musical repertoire, began the tale of an old man who turned 98. We sat up, traded back our MASH sheets, and belted, “It’s like raaaaa - e -aaaaaiiiin…!”

A song that likely calls to both Gen Xers and Millennials, “Ironic” invaded our ears from the album Jagged Little Pill and exposed coming-of-age millennials to what it meant to feel angst. Though it is a much-beloved song that speaks to these generations, it is well known that it has been frequently criticized and questioned whether or not the word “ironic” is used correctly. Art is up for interpretation once it is out for all the world to consume, so I believe the answer lies in the eye of the beholder. IMO—if Morissette can drop the term “malapropism3” (meanwhile, I had to consult the dictionary), I believe she knew what she was doing when co-writing “Ironic.”

Honorable Mentions:

“Step by Step” by New Kids on the Block, 1990

“Wannabe” by Spice Girls, 19964

Teens

“…Baby One More Time” by Britney Spears, 1999

(I was 14 years old, bound to be forever obsessed.)

I was a teenager at the turn of the millennium, sitting on my comforter-covered bed holding that bubblegum pink CD cover in my hands while listening to the album on repeat from my stereo, the Backstreet Boys, NSYNC, and LFO staring at me from the posters on my walls. My girlfriends and I thought we were the shit when singing this karaoke style, one taking the lead vocals and the other taking backup.

Does anyone know who this originator is? I know it is an impossible task, but I always like to give credit where credit is due.

Play the first three beats of that opening riff, and 100% of millennials will be able to identify this pop hit in enough time to chime in with, “Oh, baby baby!” It’s difficult not to be swept back to the late 90s and get infused with the image of Spears’ fluffy pink pigtails and risque school uniform. A song originally given the pass by R&B group TLC and pop singer Robyn, Spears landed the single that changed the trajectory of her life.56

“…very shy and super sweet …she was a kid and we had no idea there was a beast of an artist lurking under that innocent look.” —Rami Yacoub, co-producer of “…Baby, One More Time”

“The Young & the Hopeless” by Good Charlotte, 2002

(I was 17 and feeling all the teen struggles.)

I sat in the driver’s seat of my decade-old black Honda Accord, flipping through my CD case, fond of my collection: Eminem > Britney Spears > TLC > Chicago > Nirvana > burned purple CD of mixed songs. Sometime after elementary school and during the awkward-ass transition of middle school, I broadened my musical spectrum. I made my choice, slid the disc into my car stereo, and prepared to rock out and harmonize with the band that understood my trials and tribulations.

Formed in 1996, Good Charlotte graced us with the musical presence of The Young & the Hopeless in 2002. Though their star quality does not seem to be holding up as much as maybe, say, Green Day, as the band received many back-and-forth reviews, the band’s success of The Young & the Hopeless can’t be denied as it was a three-time platinum album.7

Honorable Mentions:

“What’s Your Fantasy” by Ludacris, 1999

“Breakaway” by Kelly Clarkson, 2004

20s

“Smile” by Lily Allen, 2006

(I’ve given myself the impossible task of defining my 20s with just one song…)

I stood outside of my black 1997 Honda Accord, leaning against the passenger door while shielding myself from the chill breeze sweeping the parking lot of my SoCal employer. Damian, a guy who towered over me, shut the door of his silver Camry and sauntered over. The sky was gray, threatening rain that would never materialize, making the evening feel lazy, and Damian and I were relieved we were done with our shift. Damian held out a CD case, white and decorated with Lily Allen’s name and photo. My love of “Smile” was newly discovered, and Damian was handing me Allen’s world of song that would perform on my car stereo for years to come.8

Still her top-selling single, Lily Allen debuted a sassy album that spoke to young women with Alright, Still in 2006. The fact that Allen self-promoted her music via MySpace further epitomizes the era for me.9 A meager 21-year-old, I identified with this album as I was shedding my people-pleasing habits and contemplating what I truly wanted as an independent woman.