17 Most Saddest Songs of the 90s That Will Make You Cry, Ranked, Youtube Lyrics

Most Saddest Songs of the 90s That Will Make You Cry, Ranked, Youtube Lyrics

Music has a way of capturing the most profound emotions and evoking strong memories – especially when it comes to love and heartache.

And in the 90s, some of the most iconic and heartbreaking songs were released that still tug at our heartstrings today.

So take a journey down memory lane and relive the top saddest songs of the 90s that will leave you feeling all the feels.

1. Black by Pearl Jam (1991)

“Black by Pearl Jam is often considered one of the most heart-wrenching songs from the 90s.

This alternative rock ballad tells a story of unrequited love and heartbreak, with lyrics that resonate deeply with anyone who has experienced a painful breakup.

The haunting vocals of lead singer Eddie Vedder only add to the emotional intensity of the song, making it almost impossible not to feel a lump in your throat while listening.

From lines like “I know you’ll be a sun in somebody else’s sky, but why can’t it be mine?” to “We chase misprinted lies, we face the path of time,” every word is filled with raw emotion and longing.

2. Foolish Games by Jewel

“Foolish Games” by Jewel is a heart-wrenching ballad that has stood the test of time as one of the saddest songs of the 90s.

The lyrics tell a story of unrequited love and the pain and frustration that comes with it. Jewel’s vocal carries a haunting vulnerability, making every word even more poignant.

The melody is simple yet powerful, emphasizing the raw emotions conveyed in the song.

Each line paints a vivid picture of a relationship filled with foolish games and broken promises.

This song will surely tug at your heartstrings and leave you feeling nostalgic for the emotional turmoil of young love.

3. Hallelujah by Jeff Buckley (1994)

“Hallelujah” by Jeff Buckley is undoubtedly one of the most heart-wrenching songs of the 90s that can bring tears to anyone’s eyes.

The song, initially written by Leonard Cohen, tells a story of love and loss in a hauntingly beautiful way.

Buckley’s rendition of the song is filled with raw emotion and captures the pain and sadness in every lyric.

His soulful voice, paired with the delicate guitar melodies, creates a gloomy atmosphere that is impossible to ignore.

From the first note, you can feel a longing and vulnerability that intensifies as the song progresses.

4. Kiss The Rain by Billie Myers

“Kiss The Rain” by Billie Myers is a timeless ballad that has captured the hearts of listeners since its release in 1997.

Its haunting melody and powerful lyrics tell a story of heartbreak and lost love, making it one of the saddest songs of the 90s.

Myers’ soulful vocals perfectly convey the raw emotions of longing, pain, and resignation in every line.

From the opening piano notes to the heartbreaking refrain of “Kiss the rain whenever you need me,” this song will tug at your heartstrings and leave a lasting impact.

It’s no surprise that “Kiss The Rain” has become an anthem for anyone who has experienced heartache and yearns for a lost love.

5. Baby Bitch by Ween (1994)

“Baby Bitch” by the alternative rock band Ween is undoubtedly one of the saddest songs of the 90s that can bring tears to your eyes.

From its melancholic melody to its heart-wrenching lyrics, this track captures the essence of despair and heartbreak.

The lead singer’s raw and emotional vocals perfectly convey the pain and regret of a failed relationship.

The haunting chorus, “Baby bitch, I’m better since you’ve been gone,” echoes through the song, leaving a lingering feeling of loneliness.

This heartbreaking anthem speaks to anyone who has ever loved and lost, making it relatable on a deep level.

6. Brick by Ben Folds Five

“Brick” by Ben Folds Five is an emotional ballad that has stood the test of time as one of the saddest songs of the 90s.

A haunting piano accompaniment paired with heart-wrenching lyrics tells the story of a young couple facing an unexpected pregnancy and ultimately deciding to have an abortion.

The raw and honest portrayal of their struggle with this decision, along with the sad melody, makes this song truly powerful.

Ben Folds’ distinctive voice adds depth to the track, drawing listeners in and evoking strong feelings of empathy and sadness.

7. Alice In Chains by Nutshell (1994)

Alice In Chains’ hit song “Nutshell” is a poignant and emotional depiction of pain, vulnerability, and despair.

Released in the 1990s, during the heyday of grunge music, this song remains a timeless classic that resonates with listeners today.

The haunting vocals of lead singer Layne Staley speak directly to the heart, while the accompanying acoustic guitar creates an intimate atmosphere that draws you in.

The sad lyrics tell a story of someone struggling to find their place in the world and feeling trapped within themselves.

It’s a raw and honest portrayal of inner turmoil, making it relatable for many who have experienced similar emotions.

8. I Can’t Make You Love Me by Bonnie Raitt

“I Can’t Make You Love Me” by Bonnie Raitt is a heart-wrenching ballad that speaks to anyone who loved someone who couldn’t reciprocate their feelings.

Released in 1991, this song became one of the most notable sad songs of the 90s, capturing the emotions and struggles of unrequited love.

With her soulful voice and melancholy lyrics, Raitt sings about the painful realization that no matter how much you try, you can’t force someone to love you back.

9. Disarm by The Smashing Pumpkins (1993)

“Disarm,” a haunting and emotional track by The Smashing Pumpkins, is a quintessential 90s song that transports listeners to a time of raw vulnerability and introspection.

With its poignant lyrics and sad melody, “Disarm” speaks to the struggles of growing up, the pain of broken families, and the search for inner peace.

Billy Corgan’s haunting vocals perfectly convey the feelings of despair, longing, and intensity of the song.

10. The Freshmen by The Verve Pipe

“The Freshmen” by The Verve Pipe is a powerful and emotional song that became an instant hit when it was released in the 90s.

It captures the angst and struggles of young adults trying to navigate the complexities of love and relationships.

The hauntingly beautiful lyrics depict a story of heartbreak, regret, and longing as the narrator reflects on his past mistakes with his ex-girlfriend.

The words “For the life of me, I cannot remember what made us think that we were wise and we’d never compromise” perfectly encapsulate the bittersweet feeling of looking back on a lost love with deep sadness.

11. All Cried Out by Allure Ft. 112

“All Cried Out” by Allure featuring 112 is a heart-wrenching ballad that perfectly captures the pain of a broken relationship.

Released in the late 90s, this song instantly became a hit and has since been considered one of the saddest songs of the decade.

The powerful vocals of Allure’s lead singer and the soulful harmonies of 112 create an emotionally charged atmosphere that will tug at your heartstrings.

The lyrics describe the anguish and longing felt after a breakup, with lyrics like “I gave my all, but I guess my all wasn’t enough.”

12. Fake Plastic Trees by Radiohead (1995)

“Fake Plastic Trees” by Radiohead is a hauntingly beautiful song that perfectly captures the disillusionment and emptiness in our modern world.

Released in the 90s, it is a standout track from the era’s repertoire of sad songs that have the power to make you cry.

The lyrics paint a vivid picture of artificiality and superficiality, with lines like “a green plastic watering can for a fake Chinese rubber plant,” evoking a sense of detachment and disconnection from nature and genuine emotions.

13. Nothing Compares 2 U by Sinead O’Connor

One song that is sure to tug at your heartstrings and make you shed a tear is “Nothing Compares 2 U” by Sinead O’Connor.

This iconic ballad from the 90s embodies the pain and longing of lost love in its rawest form.

The hauntingly beautiful vocals of O’Connor, accompanied by simple yet powerful lyrics, make for an emotional listening experience.

The sad melody evokes a sense of nostalgia and captures the essence of heartbreak in a way that only a few songs can.

With lyrics like “It’s been seven hours and fifteen days since you took your love away”, it’s impossible not to feel the depth of emotion conveyed through this tune.

14. Tender by Blur (1999)

“Tender” by Blur is a must-listen for anyone looking for a good cry.

This iconic song from the 90s captures the raw emotions of heartbreak and longing with its hauntingly beautiful melody and poetic lyrics.

As you listen to Damon Albarn’s soft vocals and Graham Coxon’s gentle guitar strums, you’ll be transported to a place of deep sadness and nostalgia.

The sad yet hopeful tone of the song perfectly encapsulates the bittersweet feeling of losing someone you love.

15. Heavy Heart by You Am I (1998)

“Heavy Heart” by You Am I is a heart-wrenching song that perfectly captures the emotions of sadness and longing.

Released in the 1990s, it is one of those sad songs that can still bring tears to your eyes even after all these years.

With melancholy lyrics and soulful vocals, it tells the story of a brokenhearted person struggling with their feelings and trying to move on.

The hauntingly beautiful melody, paired with raw and emotional guitar riffs, creates a powerful atmosphere that will leave you feeling nostalgic.

16. Everybody Hurts by R.E.M. (1992)

“Everybody Hurts” by R.E.M. is a timeless classic that has touched the hearts of audiences since its release in 1992.

This powerful ballad from the 90s reminds us that no matter who we are, we all experience pain and struggles in life.

The passionate lyrics and haunting melody capture the universal feeling of loneliness and isolation, making it a favorite among sad songs of the era.

With lead singer Michael Stipe’s raw and ethereal vocals, the song speaks to our deepest emotions and encourages us to push through tough times with hope for a better tomorrow.

17. Fade Into You by Mazzy Star (1993)

If you’re a child of the 90s, chances are you have a special place in your heart for Mazzy Star’s “Fade Into You.”

This hauntingly beautiful song perfectly captures the melancholic essence of the decade with its dreamy guitar riffs and ethereal vocals.

The lyrics tell a story of longing and vulnerability, making it relatable to anyone who has experienced unrequited love or feeling lost and disconnected.

It’s not surprising that this song has become an anthem for those feeling lonely or sad, and it continues to resonate with listeners even decades later.

Listening to “Fade Into You” is like taking a trip down memory lane, bringing back bittersweet emotions while providing comfort in knowing others have felt the same way.


Who were the sad singers in the 90s?

In the 90s, several notable sad singers captured the hearts of listeners with their poignant lyrics and soulful vocals.

One such artist was Alanis Morissette, whose breakout album “Jagged Little Pill” showcased her raw emotions and vulnerability through tracks like “You Oughta Know” and “Ironic.”

Another iconic name that comes to mind is Kurt Cobain, lead vocalist of the grunge band Nirvana, whose hauntingly emotional songs like “Come As You Are” and “All Apologies” resonated with many in that decade.

Other artists like Sarah McLachlan, Jeff Buckley, and Counting Crows also made a mark with their melancholic melodies that spoke to the struggles of love, loss, and loneliness.

Why do old songs make me cry?

There are a few reasons why old songs tend to make us cry. For starters, music has a powerful effect on our emotions and can elicit strong memories and feelings.

When we hear a song from our past, it may bring back memories of a specific time or person, triggering both happy and sad emotions.

Additionally, older songs often have more simple and relatable lyrics that resonate with us on a deeper level.

They tell stories and convey emotions that we can all relate to, making them timeless and able to evoke strong reactions even years later.

Furthermore, as we get older, these songs may serve as reminders of our youth or loved ones who may no longer be with us.

The nostalgia and sentimental value attached to these songs can also contribute to the emotional response they evoke in us.

Ultimately, old songs can transport us back in time and tap into our deepest emotions, which is why they have such a profound impact on us and can bring tears to our eyes.

Is it OK to cry over a song?

YES. It is okay to cry over a song.

Music can evoke strong emotions and connect with our deepest feelings.

A song can trigger memories, remind us of a particular person or moment, or strike a chord within us.

Crying while listening to music allows our emotions to be expressed and released.

It shows that we have been moved and affected by the lyrics, melody, or overall message of the song.

There is no shame in shedding tears over a song, as it can be a therapeutic experience that helps us process our feelings and find comfort in knowing that we are not alone in our emotions.

Is sad music good for you?

While some may argue that listening to sad music can bring about negative emotions and worsen one’s mood, there is evidence to suggest otherwise.

Studies have shown that sad music can have a positive impact on our mental health.

It provides a safe outlet for expressing and processing our emotions, allowing us to feel understood and validated.

Additionally, sad music can evoke feelings of nostalgia and empathy, leading to increased levels of compassion and interpersonal understanding.

Some researchers even suggest that listening to sad music can act as a form of emotional regulation, helping us cope with difficult situations in our own lives.

Of course, like any form of media or entertainment, the effects of sad music will vary from person to person.

Should I avoid sad songs?

It’s a common belief that sad songs can amplify negative feelings and make us feel even worse.

While this may be true for some people, it ultimately comes down to personal preference.

Some individuals find comfort and solace in sad songs, as they can help us process and navigate our emotions.

Music has been proven to have a therapeutic effect on our mental well-being. It allows us to release pent-up emotions and gain a sense of catharsis.

Therefore, if you enjoy listening to sad songs, there is no reason for you to avoid them.

However, if you do feel like they are negatively impacting your mood, then it might be beneficial to limit your exposure or try listening to uplifting music instead.

Should I listen to sad songs after the breakup?

After a breakup, it is entirely normal to feel sad and overwhelmed with emotions.

Many people turn to music as a source of comfort during this time, including listening to sad songs.

However, whether or not you should listen to sad songs after a breakup depends on your coping mechanism and how the music affects your mood.

If listening to sad songs brings you comfort and helps you healthily process your emotions, then it may be beneficial for you.

On the other hand, if it makes you dwell on the past and exacerbates your sadness, it might be better to avoid them.


The 90s were a decade full of powerful and emotional music that resonates with us today.

From heart-wrenching lyrics to soulful melodies, these songs captured the raw and relatable feelings of love, loss, and hope that we all experience in life.

Whether you’re looking for a good cry or want to reminisce on your angsty teenage years, the top saddest songs of the 90s are sure to strike a chord with you.

So when you need a good dose of nostalgia or emotional release, give these songs a listen and let yourself feel all the feels.

After all, that’s what music is truly meant for – connecting us through our shared emotions.

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