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Saddest Songs of 2000

40+ Songs From the Year 2000 That'll Get You All Up in Your Feels

Dec 20 2019

While the year 2000 is generally defined by Britney Spears and the Backstreet Boys hip-hopping across stages and making listeners want to do the same, there are plenty of songs that topped charts in 2000 that make us want to look out a window on a rainy day and gently touch our hands against the glass, contemplating life. Yes, sad songs certainly did exist in the world of low-rise jeans, velour tracksuits, and denim disasters, and a lot of them are still bops to this day. Here's a compilation of songs that sound sad or talk about sad, sad things to add to your 2020 playlists.

Image Source: YouTube user Britney Spears

1. "I Hope You Dance" by Lee Ann Womack

Who hasn't heard a father-daughter dance at a wedding to this song?

2. "Breathe" by Faith Hill

A beautiful love ballad about the simplicity of love.

3. "I Knew I Loved You" by Savage Garden

Love at first sight? Let's cry about it.

4. "He Wasn't Man Enough" by Toni Braxton

It's about post-breakup confidence, but it can definitely be a good song for a post-breakup cry.

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5. "There You Go" by Pink

On the hardship of having to move on from someone who is making you run in circles with their lines . . .

6. "Doesn't Really Matter" by Janet Jackson

Having to put your family and friends disapproval of your significant other to the side?! It's a heavy topic.

7. "Back at One" by Brian McKnight

The piano alone could drive you to tears, but the lyrics hit hard, too.

8. "Incomplete" by Sisqo

He is both rich and lonely, and he wants us to know.

9. "I Try" by Macy Gray

The longing! She wants them to be together, but they're not.

10. "That's the Way It Is" by Celine Dion

This is that song where Celine Dion reads a couple's minds and tells them to keep trying to work through their problems like an angel or the Ghost of Christmas Future.

11. "Show Me the Meaning of Being Lonely" by Backstreet Boys

This is 100 percent the kind of song you pretend to have your own sad music video to on a rainy day.

12. "Be With You" by Enrique Iglesias

Enrique is trying to smile through his tears because he misses you so much.

13. "No More" by Ruff Endz

If you've ever been cheated on, you might find yourself sad, angry, and confident while listening to Ruff Endz lay down a diss track on an ex.

14. "Most Girls" by Pink

Will someone just show this woman real love? It's the only thing she wants!

15. "Wonderful" by Everclear

For a song called "Wonderful," nostalgia for youth while simultaneously being scarred by your parents' fighting are pretty deep topics.

16. "He Can't Love U" by Jagged Edge

It's too little, too late, so they can only feel regret now.

17. "Separated" by Avant feat. Kelly Rowland

He hates her, he loves her, and he's lost without her.

18. "I Wish" by Carl Thomas

If you relate to unrequited love, this is your jam.

19. "Case of the Ex (Whatcha Gonna Do)" by Mya

An ex of Mya's significant other has shown up again and she's never been more confused.

20. "From the Bottom of My Broken Heart" by Britney Spears

Britney Spears moved listeners to tears in the same year she said oops and then did it again. Not to mention, she made that still-popular-today sunflower aesthetic absolutely shine.

21. "Crash and Burn" by Savage Garden

It's a happy kind of sad song because it's for a partner who's feeling alone and like the walls are closing in on them.

22. "Cowboy Take Me Away" by Dixie Chicks

What a sweet, gentle, and tearjerking Dixie Chicks ballad.

23. "Lucky" by Britney Spears

This one and its iconic music video have been making people feel for years.

24. "Never Be the Same Again" by Melanie C

It's a tragic story of regret and things changing irreversibly.

25. "Walking Away" by Craig David

He's leaving every trouble behind him in hopes of a better tomorrow.

26. "Yellow" by Coldplay

This is a timeless song for getting all of your emotions out.

27. "If Only" by Hanson

Honestly, this song is very upbeat and it throws this list for a loop, but the subject matter about being unable to tell someone how you feel fits right in.

28. "I'm Movin' On" by Rascal Flatts

This song talks about the hard task of leaving one's struggles behind if the memories are still painful.

29. "Caught Out There" by Kelis

A story about being cheated on, which seems to be a trend for the songs of 2000.

30. "Silence" by Delerium feat. Sarah Mclachlan

A ghostly song that echoes through your ears and into your tears.

31. "Again" by Lenny Kravitz

It's all about longing and learning about one's own needs in life.

32. "He's My Son" by Mark Schultz

It's a song about a father desperate to save his son. Need we say more?

33. "How to Disappear Completely" by Radiohead

The feeling of wanting to fade away from the chaos of life articulated.

34. "Again I Go Unnoticed" by Dashboard Confessional

This song talks about frustration in love and hope for a tomorrow that treats the narrator better.

35. "Ghost World" by Aimee Mann

This song articulates the desire to leave one's hometown without the means to do so, which is relatable for many.

36. "Apple Blossom" by The White Stripes

The boat is sinking and no one cares about Apple Blossom's problems . . .

37. "Only Time" by Enya

Honestly, Enya'a voice makes any song somehow sad and magical at the same time.

38. "Away From Me" by Evanescence

The sadness of feeling lost and disgusted with oneself.

39. "I'm Like a Bird" by Nelly Furtado

This song talks about the classic desire to escape, and is also just too big not to mention.

40. "By Myself" by Linkin Park

While all of Linkin Park's songs make listeners feel and feel deeply, this one's lyrics are particularly sad.

41. "Silver & Gold" by Neil Young

This is just one of those sad songs that makes you aware of time passing too quickly.

42. "Breathing" by Lifehouse

The song articulates feelings of numbness and the inability to feel at all.

43. "Stan" by Eminem

This song is both hauntingly toxic and tragic at the same time.

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