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These Are The Best Songs To Blast In Your Walkman Headphones Before You Sleep, There Is No Debate

Aflo. Shutterstock Images.

Ohhh yes. We're going all the way back to our rooms in our parents' houses today. Listen closely to the snow, landing softly on your windowsill as you imagine yourself, getting into your childhood bed around…10, 10:30 (if your parents were cool.) You've got a big day of middle school tomorrow, (the blizzard in this hypothetical wasn't bad enough to cancel school, sorry) and you just can't get to sleep. You want to stay up later, but your parents don't understand that you have an overactive mind, possibly even severe undiagnosed OCD, and there is little-to-no rest in your immediate future. Do you opt for soothing tunes, or talk radio perhaps? Lull you into a healthy 8-hour slumber before a big day of Math, English and Social Studies? No. You don't.

You whip out your walkman, and you play the HITS. Your parents want to be squares and go to bed early? Fuck them, you belong to the streets. 10:30? Sounds like a great time to get to the club! Feel like you want to have a good cry? Wow, would you look at that. Plenty of time to do it when you're not asleep! I would do this, no joke, every single night. A million different CDs, Now 5, Shakira, Now 8, Blink-182, 50 Cent - completely inappropriate for bed time, but 100% necessary to satiate those sleepless hours before your teenage brain ACTUALLY decides to shut off at night. I've narrowed the best songs, down to 10. I will hear no arguments, these are the songs, that is final. 

10. Christina Millian - AM to PM

If you weren't POPPING YOUR ASS in bed to this song, your sexual awakening wasn't intense enough. 

9. No Doubt - Spiderwebs

Listening to Gwen Stefani scream-sing about how she was dissing some guy who kept leading her on made me feel like I could actually conquer the world. I'm going to start blaming her for my narcissistic tendencies I think. 

8. Hillary Duff - Come Clean


Fun fact, the Hillary Duff Metamorphosis tour was the FIRST concert I ever went to, in my life. No idea why that is. AND, I was ENTIRELY too old to be there. Pretty sure I was like, 14. So I already loved this. Then it became the Laguna Beach theme song? FORRRRGET ABOUT IT. Mix that with a rainy night? Oh man.

7. Ludacris - Pimpin' All Over The World

This song is poetry. The lyrics are fantastic. I would listen to this over and over until I learned all of them. Still know them. Wish I had that space back in my brain for ~literally~ anything else, but Luda chose me.

6. 50 Cent - In Da Club

It was your birthday every goddamn night in that bedroom. WE GONNA SIP BACARDI LIKE ITS YA BIRTHDAY (Age 13)

5. Janet Jackson - Together Again

MY GIRL JANET. I was obsessed with how cool she seemed. Careless as hell just singing about love. Always sounded like she was floating on air. GREAT mood jam.


4. Blink 182 - The Mark, Tom and Travis Show Live Album

The entire thing. Just, the whole thing. Over and over again. Memorize the lyrics, make up stories in my head that I was some kind of troubled punk rock teenager. The greatest. 

3. Shakira - Whenever, Wherever (both the English and Spanish versions)

Shakira was so fucking hot in the streets in middle school. I remember they played this song at this…sleep away camp thing we did, at this place called Camp Bernie. It was 1 weekend with all of the kids in the 6th grade, and it was the only time I've ever "done a sleep away camp." But, they held a "dance" for us all, and it was the first time we were all bumping and grinding on each other. It was to Shakira. I relived that moment in my head through my Walkman everyday for the rest of the year. I even learned the Spanish version to hopefully one day, be able to show off that I knew the Spanish version. 

2. Usher - Confessions Pt. 2


Pt 1 also plays, but Pt 2. was THE MOST INCREDIBLE STORYTELLING I've ever heard in my life. NOBODY paints a picture like Usher. I don't even think Taylor Swift is on his level yet. Add in "My Boo" with Alicia Keys? This man is an artist with a canvas, and the canvas was the inside of my eyelids. 

1. Everclear - Wonderful

Just really fucking wallowing over here as a teenager. This song is about a broken home and how hard it is to keep pretending like everything is okay. I used to just sit there and pretend that was me (it wasn't even close) and CRY MYSELF TO SLEEP. Nothing, and I mean nothing, like a good nighttime cry to a sad ass song. 

That's it. There will be no other inclusions in this list. It is the final list, and no one should even think about debating it. XO!