25 Throwback Songs From The Lindsay Lohan Pop Era

“Oh my god,” she squealed in recognition. “Ha, I went to one of her shows in middle school or something. I remember, I even got her autograph afterwards.”

By Stephanie Karina

Updated 11 years ago, May 15, 2014

I was helping a friend pack to move when I came across a box of old photos that she had printed out to decorate her bedroom walls earlier in the year.

“Do you still want these?” I asked.

My friend had accumulated an overwhelming amount of belongings during the past four years of college. However, she was moving to a tiny apartment in Manhattan — of the variety where there is barely enough room for more than three people to stand at the same time but the rent is high enough that you would expect (or hope for) otherwise. Naturally, she needed to get rid of her stuff and we had been shoving things, left and right, into large, plastic trash bags and pitching them into the dumpster. I just wanted to make sure that I didn’t throw away anything of sentimental value on accident.

She shook her head. I started pulling photos out of the box — which we could reuse to store items she wanted to keep. I crumpled them — blurry, drunk shots from college bar nights as well as sweet, family pictures — and tossed them into the trashcan by my feet. Midway through the box, I pulled out a photo that made me do a double take. My friend — who seemed about ten or eleven — was standing next to someone who looked familiar.

“Yo,” I called, so that I could get her attention from across the room. I waved the photo at her. “Is this Lindsay Lohan? When did you meet Lindsay Lohan?”

My friend paused from scrubbing a blotch of red wine stain out of her carpet in the spot that I’d left it a few weeks ago. She came over and took the photo out of my hands, peering at it.

“Oh my god,” she squealed in recognition. “Ha, I went to one of her shows in middle school or something. I remember, I even got her autograph afterwards.”

At that moment, I remembered that Lindsay Lohan — now burgeoning reality TV star — once had a fledgling music career during the height of her fame in the early 2000s. She released her first album in 2004 and her second album in 2005, I realized after a quick Wikipedia search that made me feel incredibly old. As my friend continued to clean and pack, I took a quick (read: hour-long) break, sat in a corner with my laptop, and looked up some of Miss Lohan’s old pop hits — as well as those of her musical contemporaries at the time. Aly & AJ. Vintage Avril Lavigne. Jessica Simpson. Oof.

Enough exposition.

Here are just some of the spoils of my music search: a playlist of teenybopper pop throwback songs from back in the day (many of which I danced to at various bar and bat mitzvahs). It was Lindsay Lohan’s heyday but it was also the heyday of many an artist that has sadly fallen from public spectacle. This playlist spans the good, the bad, and the downright ugly (but still annoyingly catchy). Don’t be ashamed to bop your head to these tunes!

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1. “Rumors” – Lindsay Lohan

[youtube http://www.youtube.com/watch?v=ODTRrT-ONxA%5D

2. “Potential Breakup Song” – Aly & AJ

3. “Wake Up” – Hilary Duff

4. “With You” – Jessica Simpson

5. “Leave (Get Out)” – Jojo

6. “Sk8er Boi” – Avril Lavigne

7. “Cupid’s Chokehold” – Gym Class Heroes

8. “Miss Independent” – Ne-Yo

9. “Behind These Hazel Eyes” – Kelly Clarkson

10. “She Will Be Loved” – Maroon 5