1.“One Sweet Day” - Mariah Carey ft. Boyz II Men

This is one of those songs that you belt out without realizing how sad it really is. The melody might be beautiful and nostalgic, but the lyrics are as sad as it gets.

2."Purple Rain" - Prince

Whew. From the guitar solo to the "oos" at the end, get ready to get all the way in your feelings.

3."Rainy Dayz" - Mary J. Blige ft. Ja Rule

It will have you looking out the window, shaking your head, and singing every word.

4."Backstabbers" - The O'Jays

It might not be a song about a breakup, but jealous "friends" you have to side-eye aren't necessarily fun either.

5."Try Sleeping With a Broken Heart" - Alicia Keys

Just the thought of sleeping with a broken heart is enough to make you sad. Alicia just takes it up a notch.

6."All Falls Down" - Kanye West ft. Syleena Johnson

The old Kanye had a way of getting us into our emotions, and this song, along with the video, was no exception.

7."I Have Nothing" - Whitney Houston

I mean, there are few songs that make us bare our souls like this one. It can leave you drained before you even realize what happened.

8."I Miss You" - Aaliyah

Who else felt that "Off to college, yes you went away" line every time?

9."Ain't No Way" - Aretha Franklin

Ready to love someone who refuses to let you (or love you back)? The legendary Aretha Franklin makes it OK to mourn that moment in this ballad.

10."Marvin's Room" - Drake

Drake is just as emotional as most of us, and he had no shame in showing his regrets with an ex.

11."Dance With My Father" - Luther Vandross

You didn't have to be grown to feel the gravity of Luther's emotions.

12."Hello" - Adele

If anyone can make you feel sad about your true love not answering your calls, it's Adele.

13."End Of The Road" - Boyz II Men

When the end of a relationship is too much to bear, Boyz II Men is there to help us cope.

14."Lost Ones" - J. Cole

Even if you don't know all of the words, the story itself is enough to be sad by the time the outro fades.

15."Un-Break My Heart" - Toni Braxton

Toni, Toni, Toni. This song is at the top of the breakup soundtrack.

16."See You Again" - Wiz Khalifa ft. Charlie Puth

There are fewer things worse than losing a close friend and not being able to share life's moments with them.

17."Broken-Hearted Girl" - Beyonce

When begging someone to stay just doesn't work.

18."When I Was Your Man" - Bruno Mars

You can literally feel the pain of a good thing gone bad.

19."Dreaming Of You" - Selena

When the love of your life may or may not feel the same way, the best thing you can do is dream about them.

20."Save The Best For Last" - Vanessa Williams

The song has its positive moments, but for some reason, it can put you in a mood.

21."Yo Side Of The Bed" - Trey Songz

If the song isn't enough to make you cry, the video will do it.

22."Ex-Factor" - Lauryn Hill

Every lyric is a monumental one to get you emotional.

23."Stay" - Rihanna ft. Mikky Ekko

You might as well cry yourself to sleep on this one.

24."Unpretty" - TLC

You might be sad, but you'll still be unapologetically you.

Are you a member of our insiders' squad? Join us in the xoTribe Members Community today!