1

"Foolish Games" — Jewel

Just like Jewel's man was tearing her apart, "Foolish Games" tore you apart (and maybe still does). I recommend listening to both the radio version and the album version off of Pieces of You for the full emotional impact.

2

"Kiss The Rain" — Billie Myers

Long distance takes its tolls on relationships . This song seemed so deep to me at the time, but now I realize just how truly '90s melodramatic it really is.

3

"Brick" — Ben Folds Five

Ben Folds and his band proved that you only need four minutes and 30 seconds to completely emotionally devastate people with this song about his girlfriend getting an abortion when they were younger. This song still packs a punch today.

4

"I Can't Make You Love Me" — Bonnie Raitt

This song is about being only a booty call when the term "booty call" didn't even exist. While you might have missed the message of this adult contemporary song if you were a kid in the early '90s, you surely recognized its crushing power before the decade was through. "I Can't Make You Love Me" may even beat out Carole King's "Will You Still Love Me Tomorrow" as the ultimate song about unrequited love the next day.

5

"All Cried Out" — Allure Ft. 112

In the '90s, Allure joined forces with 112 to take on Lisa Lisa and Cult Jam's '80s song. When they sing, "Don't you know my tears will burn the pillow," you became all cried out too.

6

"The Freshmen" — The Verve Pipe

While you might not know the exact story The Verve Pipe is telling in this song, "guilt-stricken, sobbin' with his head on the floor" is about where you were if you listened to "The Freshmen" on repeat in the '90s.

7

"Nothing Compares 2 U" — Sinead O'Connor

Sinead O'Connor's raw earestness may not be for everyone, but this is the stuff I live for. When "Nothing Compares 2 U" comes on, cease all other activities and commence ugly crying — in the '90s and today.

8

"Weird" — Hanson

If you related to the line, "When you live in a cookie cutter world/Being different is a sin/So you don't stand out/And you don't fit in," Hanson's "Weird" was surely the jam you sat in your room and cried to in the '90s.

9

"Angel" — Sarah McLachlan

10

"Tears In Heaven" — Eric Clapton

If you were born in the '80s or '90s, you might have known Clapton less for his rock days intially and more for this devastating song about his child's death that received a lot of radio play. "Tears in Heaven" is about Clapton's 4-year-old son, who died falling out of a New York City window, and even if you were just a kid yourself when you first heard the song, you knew how horrible that was.

11

"My Heart Will Go On" — Celine Dion

Your instinct may be to deny that you ever cried to "My Heart Will Go On," but I want you to travel back to 1997 when you heard the Celine Dion song after first seeing Leonardo DiCaprio die in Titanic. If you didn't shed a tear at least once while listening to this song in the '90s, then you're as ice cold as Jack Dawson's grip.

12

"Kissing You" — Des'ree

Another song that made you cry thinking about the fate of a DiCaprio character was Des'ree's song from Romeo + Juliet, "Kissing You." She performed it when Romeo and Juliet first see each other in the 1996 movie and the feelings this song brings out to this day are all too real.

13

"Show Me The Meaning Of Being Lonely" — Backstreet Boys

I still don't know the meaning of being lonely, but I do know that AJ McLean, Howie D., Nick Carter, Kevin Richardson, and Brian Littrell always had the ability to make me cry with this song.

14

"Me" — Paula Cole

While not as popular as her two previous singles — "Where Have All the Cowboys Gone?" and "I Don't Want to Wait" — her raw vocals on the bridge were tear-inducing if you were doing some preteen soul-searching.

15

"Everybody Hurts" — R.E.M.

Sure, it might be a little too on the nose, but that doesn't mean that Michael Stipe didn't affect you at least once in the '90s when he sang about everybody hurting ... sometimes.

16

"From The Bottom Of My Broken Heart" — Britney Spears

Even if you hadn't experienced losing your "first love" or "true love" yet, Britney Spears' song off her first album had you crying like you had. You may have also weeped because you wanted to look as good as she did in a bucket hat (guilty as charged).

17

"I Swear" — All-4-One

Although this song's message is actually sweet, it made you cry yearning for the day when you'd have someone who loved you as much as All-4-One loved the subject of "I Swear."

18

"Hallelujah" — Jeff Buckley

Although this is originally Leonard Cohen's song, Jeff Buckley's 1994 cover is one of the most memorable. Perhaps you weren't cool enough to know it as a kid back in the day, but it definitely has made you cry since then.

19

"Killing Me Softly" — Fugees

The song that was made most famous by Roberta Flack before Lauryn Hill updated it in the '90s killed you softly too.

20

"Viva Forever" — Spice Girls

The second-to-last song on Spiceworld was much more serious than "Spice Up Your Life." Maybe it was that stark contrast of joy and melancholy that made you cry so much listening to "Viva Forever" in the '90s (she says, trying to rationalize her intense Spice Girls feelings).

21

"It's So Hard To Say Goodbye To Yesterday" — Boyz II Men

This a cappella remake of this '70s song might be often used as a joke now, but don't even pretend its sincerity didn't affect you in the '90s.

Now that you've been crying to '90s songs, perhaps you should listen to the happiest songs of the decade to complete your emotional rollercoaster. After all, many of the artists on this list were there for you in times of happiness too.