39 Songs That Will Remind Every Millennial Of Summer Break

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

BlackEyedPeasVEVO on YouTube

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

2. "Best I Ever Had" — Drake

MusicNerd456 on YouTube

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

3. "You Belong With Me" — Taylor Swift

TaylorSwiftVEVO on YouTube

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

4. "Fire Burning" — Sean Kingston

seankingstonVEVO on YouTube

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

LadyGagaVEVO on YouTube

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

RihannaVEVO on YouTube

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

7. "Pocketful Of Sunshine" — Natasha Bedingfield

NBedingfieldVEVO on YouTube

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

TPainVEVO on YouTube

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

shakiraVEVO on YouTube

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

10. "Crazy" — Gnarls Barkley

Downtown Records on YouTube

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

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

thefrayVEVO on YouTube

This song was the saddest, catchiest song that summer.

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

Radial by The Orchard on YouTube

Very into any song with hand motions.

13. "Hollaback Girl" — Gwen Stefani

GwenStefaniVEVO on YouTube

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

NastiaLiukinFreakMmM on YouTube

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

15. "Confessions Part II" — Usher

UsherVEVO on YouTube

A contender for song of the decade, IMHO.

16. "The Reason" — Hoobastank

HoobastankVEVO on YouTube

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

17. "Lean Back" — Terror Squad

TerrorSquadVEVO on YouTube

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

ChristinaMilianVEVO on YouTube

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

beyonceVEVO on YouTube

Truly an icon, this one.

20. "It's Gonna Be Me" — 'N Sync


To be revived every year come April 30.

21. "Try Again" — Aaliyah

Tengu Ruu on YouTube

R.I.P., Aaliyah.

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

DestinysChildVEVO on YouTube

Almost enough to break out your pleather halter top.

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

NineDaysVEVO on YouTube

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

TrainVEVO on YouTube

But tell me: what does this mean?!

25. "Hot In Herre" — Nelly

NellyVEVO on YouTube

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

26. "Complicated" — Avril Lavigne

AvrilLavigneVEVO on YouTube

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

27. "Without Me" — Eminem

EminemVEVO on YouTube

Note the phone used to call Dr. Dre.

28. "Dilemma" — Nelly Feat. Kelly Rowland

NellyVEVO on YouTube

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

29. "Foolish" — Ashanti

AshantiVEVO on YouTube

Awww, remember Ashanti?

30. "The Middle" — Jimmy Eat World

JimmyEatWorldVEVO on YouTube

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

31. "A Thousand Miles" — Vanessa Carlton

VanessaCarltonVEVO on YouTube

This song was classic.

32. "Get Busy" — Sean Paul

Atlantic Records on YouTube

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

CAguileraVEVO on YouTube

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

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

Neka lovmytwo on YouTube

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

Aldo de Jesús Santos Ríos on YouTube

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

TLCVEVO on YouTube

Even Scream Queens knows what's up.

37. "Don't Turn Around" — Ace Of Base

Ace of Base (Official) on YouTube

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

38. "MMMBop" — Hanson

HansonVEVO on YouTube

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

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.