7 of the Saddest Live Performances

Sometimes, you just need to have a good cry.

If that sounds like something you might be interested in, please go ahead and press play on the following seven videos, featuring some of the greatest artists of all time performing at their most vulnerable. Man, the 90’s were sad.

Eric Clapton – ‘Tears in Heaven’, 1992

This is the first time Eric Clapton played ‘Tears in Heaven’, the song inspired by the death of his four-year-old son, Conor, who fell from the window of a New York apartment in 1991. After a sit-down interview with English broadcaster Sue Lawley, Clapton picked up the guitar and debuted the heartbreaking song to the public. Unsure how Lawley was able to keep it together under the circumstances, but she managed to hold her composure long enough to tell him the song is ‘going to make a lot of people cry.’ She was correct.

Jeff Buckley – Satisfied Mind,  1992

Watching any Jeff Buckley performance is kind of sad given the circumstances of his untimely death at only 30-years-old. Five years before his mysterious drowning, a short-haired Buckley played a set at the Knitting Factory in New York in March of ’92. At this time, his club and café performances were just starting to generate some buzz, but I can’t help but imagine how shocked the majority of the crowd were at the Knitting Factory on this night. Actually, I don’t really have to imagine—you can hear it in the video. The minute he starts singing, the whole room goes quiet.

Elliott Smith – ‘Miss Misery’, 1998

Speaking of artists who can make you sad just by the mention of their name—here’s Elliott Smith breaking hearts at the Oscars. He was asked to perform ‘Miss Misery’, which appeared on the Good Will Hunting soundtrack and was subsequently nominated for an award. At the time, he was relatively unknown (at least among the crowd he was playing to that night), and the story goes that he wasn’t really looking forward to performing. Of his first and last night at the Oscars, Smith said, ‘I wouldn’t want to live in that world, but it was fun to walk around on the moon for a day.’

Tori Amos – ‘Me and a Gun’

Tori Amos’s 1991 track, ‘Me and a Gun’, is without a doubt one of the most devastating songs ever written. When Amos was 21-years-old, an audience member at a bar she was playing at asked for a ride home. He raped her at knife-point, telling her throughout the ordeal that he was going to kill her when he was finished. She managed to escape, and grappled with why she was able to survive the encounter when other women had not. This performance of the song, to a completely silent audience a few years after its release, will break you into pieces. Do not press play unless you are prepared for this outcome.

NIN – ‘Hurt’, 1995

This performance of NIN’s ‘Hurt’ is so masterful that it also serves as the official music video for the song. The video was actually recorded before a show in Nebraska, in February of 1995. Arguably the heaviest song ever written about drug abuse and the self-loathing that comes with it, Trent Reznor was in the midst of his heroin addiction at the time of this performance. Reznor actually credits David Bowie, who he toured with in ’95, with helping him get clean. According to Reznor, Bowie told him, ‘You know, there is a better way here, and it doesn’t have to end in despair or in death.’

David Bowie – ‘Life on Mars’, 2005

Speaking of Bowie, here he is performing in public for the last time, as part of a charity concert called The Fashion Rocks show at Radio City Music Hall in New York. A year prior to his performance, Bowie suffered his first heart attack while on tour in Hamburg. This rendition of ‘Life on Mars’ is sad for many reasons, marking the beginning of a long health battle that ended with his death a decade later. Prepare ze goosebumps.

Fiona Apple – Sullen Girl, 1998

This here is an 18-year-old Fiona Apple performing a song she wrote when she was 16-years-old, the hauntingly beautiful ‘Sullen Girl’ from her debut record, Tidal. Six years before this performance, Fiona was raped outside of her home, and the assault left her battling with an eating disorder for years. The lyrics, ‘But he washed me ‘shore / and he took my pearl / and left an empty shell of me’ are reportedly a reference to her rapist, and the way she sings them here is really something else.

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