39 Songs That Will Remind Every Millennial Of Summer Break

LOS ANGELES, CA - OCTOBER 14: Recording artist Avril Lavigne performs at the premeire of Nokia Productions' Spike Lee Collaboration film held at the Nokia Theater L.A. Live on October 14, 2008 in Los Angeles, California. (Photo by Alberto E. Rodriguez/Getty Images)
Source: Alberto E. Rodriguez/Getty Images Entertainment/Getty Images
You know how any popular track that comes out when the weather's warm is deemed the "song of the summer"? That title goes back a long way. For decades now, the most blazing hits to spark the airwaves between Memorial Day and Labor Day have been given that label. For instance, if you remember anything about what it was like to be alive in the summer of 1999, you'll recall that you couldn't walk into a public establishment or turn on the radio without hearing Christina Aguilera's "Genie In A Bottle," That song, like any good summer anthem, just seemed to be everywhere that season, and same goes for Beyonce's "Crazy In Love" during summer 2003; if you somehow managed to be one of the 10 people in the country who went that entire summer without hearing that track, you were probably still in your Y2K bunker. 

But in the spirit of summer jams still worth breaking out your old boombox for, look no further than this list. Below are some of the best songs from the mid-'90s to the late-2000s that are sure to remind every millennial of summer, and believe me — you're gonna want to give many of these a re-listen ASAP.

Late 2000s:

1. "I Gotta Feeling" — The Black Eyed Peas

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You're right, Black Eyed Peas. Tonight will be a good night.

2. "Best I Ever Had" — Drake 

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Circa the era when people were still like, "Hey, did you know that guy was on Degrassi?"

3. "You Belong With Me" — Taylor Swift 

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The signs-in-the-window gag is still an internet gift that keeps on giving.

4. "Fire Burning" — Sean Kingston 

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Catchy, to be sure, but did Kingston consider how irresponsible it was to encourage people to dial 911 in non-emergencies?

5. "Lovegame" — Lady Gaga 

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I still have no idea what half the lyrics are talking about to this day, but it's hard not to love Gaga in this iteration.

6. "Umbrella" — Rihanna feat. Jay-Z

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How did this not result in outerwear sponsorships for young RiRi?

7. "Pocketful Of Sunshine" — Natasha Bedingfield 

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A seasonally-appropriate choice, made even more famous thanks to the Emma Stone film Easy A.

8. "Buy U A Drank (Shawty Snappin')" — T-Pain Feat. Yung Joc 

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Included because there's almost a 100% chance that some guy in cargo shorts sang this to you at a party 10 years ago.

Mid 2000s:

9. "Hips Don't Lie" — Shakira

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This is another song where I have no idea what's going on lyrically, but I still love nonetheless.

10. "Crazy" — Gnarls Barkley 

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The commercial peak of Cee Lo Green and Danger Mouse's musical collab.

11. "Over My Head (Cable Car)" — The Fray 

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This song was the saddest, catchiest song that summer.

12. "Snap Yo Fingers" — Lil Jon Feat. E-40 & Sean Paul Of The YoungBloodZ

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Very into any song with hand motions.

13. "Hollaback Girl" — Gwen Stefani 

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Circa the era when Gwen couldn't seem to go anywhere without her costumed backup dancers.

14. "Lose Control" — Missy Elliott Feat. Ciara & Fat Man Scoop 

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I have no idea who this Fat Man Scoop character is, but I'd like to shake his hand.

15. "Confessions Part II" — Usher

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A contender for song of the decade, IMHO.

16. "The Reason" — Hoobastank 

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Too bad this band hasn't stuck around. I miss hearing the name.

17. "Lean Back" — Terror Squad 

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Again, my affinity for song choreography rightfully places "Lean Back" on this list and I don't feel the need to explain myself further, but I still sort of feel weird about it.

18. "Dip It Low" — Christina Milian

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I'm hoping Milian has another "Dip It Low" on her hands that'll be released one of these days.

Early 2000s:

19. "Crazy In Love" — Beyonce Feat. Jay-Z

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Truly an icon, this one.

20. "It's Gonna Be Me" — 'N Sync 

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To be revived every year come April 30.

21. "Try Again" — Aaliyah 

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R.I.P., Aaliyah.

22. "Jumpin', Jumpin'" — Destiny's Child 

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Almost enough to break out your pleather halter top.

23. "Absolutely (Story Of A Girl)" — Nine Days

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This is still the saddest song to me ever, and even though I know Adele and Sam Smith exist now and that shouldn't be the case, it is.

24. "Drops Of Jupiter (Tell Me)" — Train 

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But tell me: what does this mean?!

25. "Hot In Herre" — Nelly

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Get out your Band-Aids. The king of the south means business.

26. "Complicated" — Avril Lavigne 

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...Or, alternatively, your tank top-and-tie ensemble.

27. "Without Me" — Eminem 

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Note the phone used to call Dr. Dre.

28. "Dilemma" — Nelly Feat. Kelly Rowland 

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...Same with the Excel document Kelly used to text Nelly.

29. "Foolish" — Ashanti 

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Awww, remember Ashanti?

30. "The Middle" — Jimmy Eat World 

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This to me feels sort of timeless. Maybe I'm just a hopeless millennial.

31. "A Thousand Miles" — Vanessa Carlton 

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This song was classic.

32. "Get Busy" — Sean Paul 

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This is what I hear when I hear this song: Shake. That. Thing. Miss. [Inaudible].

Mid To Late 1990s:

33. "Genie In A Bottle" — Christina Aguilera

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Isn't it weird to think that there was a time when Britney and Christina were rivals?

34. "The Boy Is Mine" — Brandy & Monica

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Love everything about this music video, including but not limited to the unexpected Jerry Springer appearance on Brandy's TV.

35. "Macarena (Bayside Boys Mix)" — Los Del Rio

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So how did this song work? Did people just do their homework while listening to this song or was it always reserved for sporting events?

36. "Waterfalls" — TLC

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Even Scream Queens knows what's up.

37. "Don't Turn Around" — Ace Of Base

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Mostly because this reminds me of the summer I spent listening to AOB on repeat in college.

38. "MMMBop" — Hanson 

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Serious inquiry: How many times do you think the Hanson brothers have gotten asked to define the word "mmmbop"?

39. "Baby Got Back" — Sir Mix-A-Lot

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Another very serious inquiry: Do you think Sir Mix-A-Lot sent Nicki Minaj flowers after her sample in "Anaconda"?

Now that there's no longer a need for mix tapes, what will our kids will do when they want to give someone a collection of music? Send it via hologram? Listening to these great songs inspires so many questions.

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