Top 5 Sad Songs of the 00s

No matter if it’s trying to reignite an old flame or dealing with quarantine-induced long-distance drama, here are some songs to help ease your transition.

Natasha Khan’s subtle vocals perfectly convey the heartbreak of having lost love in this track, from soft verses to an epic ballad-style bridge where she pleads with an old flame to return.

Back To Black by Amy Winehouse

the 2000s brought us some unforgettable music. From sweaty danceable post-punk, earnest folksy acoustic fare and quirky eclectic pop, even emo-adjacent rock got in on the action, with its emotive lyrics and gritty production. No album of this decade could ever rival Amy Winehouse’s Back to Black as far as its melancholy melodies and tale of addiction and heartache remained as deeply personal to many listeners for over a decade – perhaps due its moving melodies or tragic story of addiction and heartache it still haunts listeners’ minds even today.

Back to Black was released as the second single from Amy Winehouse’s self-titled 2007 album and discusses their tumultuous relationship with Blake Fielder-Civil (who left her for another woman). Winehouse opens up about her struggles with depression and addiction as well as past heartaches and the desire for redemption through this emotional track.

Musically, this song was produced by Salaam Remi and Mark Ronson, who had collaborated with Winehouse on her debut album Frank. They helped capture girl group soul sounds of the 1960s while mixing it with contemporary R&B and neo-soul sounds to produce an album which is both moving and melancholy yet upbeat and catchy.

It was a massive hit both in the US and UK, reaching number eight on Billboard Hot 100 (US) and becoming Winehouse’s third best-selling single there. Additionally, it appeared in several year and decade-end lists of songs as one of the greatest of its genre and became one of her signature tunes; Beyonce and Andre 3000 covered it on their 2013 soundtrack for The Great Gatsby film soundtrack.

The music video for “Amy Winehouse’s Heartache” was an emotional depiction of mourning and loss, featuring Winehouse in front of a gravesite that read “Here Lies the Heart of Amy Winehouse.” After Amy Winehouse died from alcohol poisoning, this sentimental gesture was edited out from promotional clips.

Breathe Me by Sia

Sia’s debut single remains one of the most beautiful and poignant songs you will ever hear. Ten years since she first donned her iconic wig, this track from Colour the Small One remains as emotional and moving as ever. Sia reveals in the video that it deals with anxiety and self-harm – though she managed to overcome both herself. Sia knows there are others struggling and it is vital that more be said about mental health issues.

This was your go-to emo song when someone betrayed you (which happened quite frequently in middle school). As tears flowed from your eyes and you clutched tissues close, listening to this was probably one of the only times in life where you truly experienced teenage angst – making this time worthwhile and memorable.

As you read your first Twilight book in solitude, it was impossible not to feel sad for Bella and Jacob. Mark Hoppus captured these feelings perfectly with this track – an essential listen for anyone experiencing a relationship breakup!

Breathe Me was another song that provided us with insight into Sia’s struggles before she opened up about them more publicly. According to Sia herself, Breathe Me is about feeling worried, generally anxious, and sometimes overwhelmed by your own inner dialogue so much so that you have some sort of conniption fit and potentially harm yourself.” Sia wrote this song during her battle against drug and alcohol addictions before trying suicide the night of its creation; thanks to a friend calling 911 on her behalf she was saved from dying by friends calling them in.

High school was filled with bad days, from not being accepted by your crush to mom not allowing you to stay out after 9 or the loss of a Chia Pet – every occasion required an emotional release through song. “Downtown” always made us cry; it helped express all our angst while simultaneously reminding us all that everything would eventually work itself out.

My Immortal by Amy Lee

The 2000’s weren’t defined only by an abundance of weird mp3 blogs; they also witnessed an era of heartache-inducing songs from artists like PJ Harvey and Liz Phair; garage rock revival, emo-adjacent rock music; it was an era full of songs about breakups, betrayals, and the end of innocence-all thanks to Evanescence!

This piano ballad narrator mulls over her past relationships, recalling how perfect she once was for one particular suitor. It makes you weak at the knees while simultaneously sending hormones soaring (even if you were just 13!). Like a tween version of Good Charlotte, this song always made me tear up!

My Immortal was co-written by Evanescence guitarist Ben Moody and Lee, and featured on various EPs and demos released prior to Fallen. However, Wind-up Records decided against Lee’s wishes and included it on their debut album instead reworking the demo recording with synthesizers and adding strings by composer Graeme Revell.

Lee is known for her melancholic yet soothing vocals; she can easily put you in an emotional state through her melodies, which often feature string sections to bring tears to your eyes. Regardless of what else may make you cry, Lee never fails to deliver an unforgettable musical experience!

Taylor Swift has long been celebrated for exploring the inner workings of her own love life, and this gorgeous ballad about an unsatisfactory one-night stand doesn’t disappoint. Swift paints an image of haunted bars, boarded-up windows, and hangover mornings that leave one reeling with pain – an emotionally-evocative song that’ll have you experiencing every agonizing detail of their situation first hand.

People Who Died by The Verve Pipe

Teenagers of the 2000s would likely recognize this heartbreaking tune. Even now, its lyrics about a woman having an abortion before taking her own life remain seared into our memories. According to Brian Vander Ark of Verve Pipe’s Brian Vander Ark reveals that this song was inspired by a real event (though with some altered details such as suggesting she overdosed on Valium to commit suicide instead of actually getting an abortion).

After nearly two decades since The Verve Pipe last had a chart hit, they continue to earn fans and continue performing live. Their ninth album Threads will be released later this fall and explores how we are connected by an invisible thread that weaves its way through our lives, stretching and bending but never breaking. Channing Lee came up with its name from an ancient Japanese proverb which states people share one common fate that never breaks or ties.

The title track of The Verve Pipe’s new album addresses themes such as addiction, loss and the longing for something greater. One song which captures this feeling of stagnation is “Miserable At Best”, written about a friend battling depression who felt life had no purpose – an iconic ballad recorded for the first time by them, becoming one of their biggest hits to date.

Vander Ark recently spoke with American Songwriter about this song and explained that writing it outside his comfort zone and paying attention to what was going on around him was challenging, yet yielded authentic sounding music.

After the release of their album, The Verve Pipe released several more releases – such as “Photograph.” However, no one could argue against “Villains” being their biggest hit and one of the saddest songs ever. It peaked at number five on Billboard modern rock chart and contributed towards making their sophomore RCA release, Villains, a platinum success.