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Top 10 Greatest Sad Covers From The Last 20 Years

Emily Thomson Student Contributor, University of Victoria
This article is written by a student writer from the Her Campus at U Vic chapter and does not reflect the views of Her Campus.

There is something really special about one of your favourite artists covering a song from another one of your favourite artists. It’s kind of like when Disney Channel would have those crossover episodes and your whole life seemed complete. 

There are a huge number of song covers in the world. Each one contributes to the special phenomenon in the music industry where somebody takes someone’s personal creation and honours it in their own way. Sometimes the artist might make it better and end up getting all the credit, and some just remind us of how good the original is… In the name of good journalism, let’s talk about some of the best covers of sad songs out there and where they come from (in no particular order). 

“Somebody Else” by Role Model

Tucker Pillsbury, under his stage name ‘Role Model’, covered The 1975’s iconic song “Somebody Else” in 2024. The original, written by lead singer Matty Healy, was released in 2016 as a single for their upcoming album at the time. The original has more of a mellow, synthetic production, but with a driving beat. On top is the staple spacey, emotive, layered vocals from Healy. The song is a beautiful and raw description of the post-breakup struggle of seeing them with ‘somebody else’. 

Role Model decided to cover the song in a completely new genre, removing the indie-esque synths, and adding bright guitars and a happy beat to make the song more of a pop hit, with little hints of country-pop. Role Model’s voice is sweet and strong and captivatingly fun. He makes the song sound like it’s being performed live and creatively manipulates the listeners into thinking we are having a good time, even though the lyrics are anxiety-spiral-inducing.

“Moon River” by Frank Ocean 

Frank Ocean gifted us with his cover of “Moon River” on Valentine’s Day in 2018. The original song was composed by Henry Mancini with lyrics written by Johnny Mercer in 1961 and was sung by Audrey Hepburn in the movie Breakfast at Tiffany’s. The song won an Academy Award for Best Original Song in 1962. The original “Moon River” has an antiquated, comforting sound to it, with simple muted guitar strums, a distant orchestra filling in the space, and Hepburn’s breathy, vintage-English vocals sealing the deal. 

Frank Ocean’s cover is a raw, emotive, and addictive homage to the original. He made the song his own with his endless layering and harmonies, gentle electric guitar, and melancholic keyboard. The lack of percussion pulls you into the space of the song and allows you to focus on Ocean’s raspy, emotional, and strong vocal ability. 

“Girl Crush” by Harry Styles 

Girl Crush” is a song written by Lori McKenna, Hillary Lindsey and Liz Rose, and performed by the country band Little Big Town. It was released in 2014 and is their most streamed song. They offer a powerfully simple and captivating version of the song, with a melodic distorted guitar plucking throughout, slow percussion, and spacey layered harmonies. 

Harry Styles takes this song to a new level. He covers it live at Metropolis Studios in London, with background harmonies and an acoustic guitar, creating a painfully beautiful rendition of the song. It immediately sounds even more sad and slow, and Styles’ raspy, powerful, and soulful voice encapsulates the emotion of the lyrics. If any song will put you into a trance, it’s this one.

“Do I Wanna Know?” by Hozier

The Arctic Monkeys released the renowned “Do I Wanna Know?” in 2013, which has amassed over 2.2 billion streams on Spotify. This alternative rock staple has a distinct electric guitar riff introducing the listener to all of its bad-ass, dark and seductive entirety. It is full of distorted guitars, intense drums, and layered adlibs. The song’s lyrics have a dark romantic demeanour, which perfectly compliments the intense vibe of the song. 

The most drastic yet well-executed cover of a song in a long time is Hozier’s rendition of “Do I Wanna Know?”, which takes the already phenomenal, intense rock song, and turns it into a mellow, sad and beautiful version of itself. The cover was recorded live at The BBC and features a simple collection of instruments including an electric guitar, gentle drums, and a cello that solidifies the somberness of the song. Hozier’s deep, strong, bluesy vocals fit beautifully on top of the song and pair with sweet, distinct harmonies. While this cover has had a recent resurgence in popularity online early in 2025, it was released in 2014, shortly after he made a name for himself with “Take Me To Church”.

“Make You Feel My Love” by Adele

I truly believe that, while Bob Dylan is the original artist of the classic song “Make You Feel My Love,” it was made for Adele. Dylan originally released it in 1997, with his classic nasally, raspy, and unique voice carrying the song’s emotional lyricism. It has a distorted piano playing the chords, with an ambient organ playing along it. 

Adele’s version adds a unique piano melody that carries the song’s sweet yet powerful sound. Adele is one of the best vocalists of our time, and she does this song justice by making it her usual sound, with bright, remarkable vocals and accompanying piano—the perfect ballad. A vital component of Adele’s cover is the string orchestra solo and background melodies. String instruments have an evocative nature and complement the song beautifully.

“Dancing On My Own” by Calum Scott

Dancing On My Own” is an uplifting, synth-driven, pop hit released in 2010 by the Swedish singer-songwriter Robyn. It’s a fast-paced danceable song with a driving beat and Robyn’s catchy layered vocals. This song is another example of an artist somehow making you feel like you are having the time of your life, but if you pay attention to the lyrics you may break out into tears. 

Calum Scott decided to break all of our hearts by taking away the distracting, danceable beat and turning this song into an overwhelmingly tragic yet beautiful ballad. Not only did Scott make this song his own, it’s what made him famous! Scott first sang “Dancing On My Own” as his audition for Britain’s Got Talent back in 2015, winning himself the Golden Buzzer—an immediate pass to the semi-finals. He released it as a cover in 2016 due to his audition’s abundant recognition. He slows the song down, incorporates long notes and vocal riffs, and belts out the emotional chorus. His voice is smooth and powerful and perfectly encapsulates the rawness of the lyricism in this song.

“That Funny Feeling” by Phoebe Bridgers 

In 2021, Bo Burnham released his satirically relevant song, “That Funny Feeling,” which touches on the persistent anxiety of living in our day and age, directly referring to current socio-political circumstances. His use of irony, hyperbole, and honesty makes this song unique, impactful, and completely relatable. 

When Phoebe Bridgers covered it in the same year, it enhanced the song with that classic Phoebe sweet sadness. Her voice navigates the quick lyrics and makes it sound seamless, all while using her breathy, whispery vocals to make the song more sad than it already was. Not many people could pull off the eccentric nature of this song and still make you want to cry, but Phoebe Bridgers does.

“A Song for You” by Donny Hathaway

Leon Russell originally released his song “A Song For You” in 1970 for his debut solo album. With a solid, standard piano to carry the song, he plays it at a slightly faster pace, with a bit more warmth to it from the country twang in his vocals. He has a unique whine in his singing style that makes the song feel quite desperate and dramatic (in a good way).

Donny Hathaway came in and stole the show with his cover of this song in 1971. His vocal ability is unmatched and resonates so powerfully with such an intense song. His deep vibrato and smooth vocal runs make the song somber and strong. The cover keeps you on your toes the entire time, waiting for the next note sung and chord played. Hathaway’s voice, mixed with the orchestra and bluesy piano, makes this the most emotive cover that draws you in and keeps you there until the very last note. It aired in the season finale of Euphoria in 2019, which gives me reason enough to include it in the last 20 years of best covers. 

“No Surprises” by Jeremiah Fraites & Gregory Alan Isakov

No Surprises” is a classic song from Radiohead, released in 1997. It demonstrates Radiohead’s experimental alternative rock nature but is more on the sad side of things. It includes their classic use of ambient sounds, electronic synths and unconventional structures. The original has little bells that make the song slightly happier sounding than the incoming cover. 

Jeremiah Fraites composed an orchestra-full cover for Gregory Alan Isakov to sing over. It has a cinematic nature to it with a full symphony accompaniment to classic piano chords. The composition in itself is a masterpiece, and the pairing of Isakov’s raspy, gentle singing style makes for an extremely sad and dramatic outcome. 

“Helpless”, by K.D Lang

Last, but definitely not least, we have Neil Young’s infamous “Helpless,” originally released in 1978. It’s a classic Neil Young banger—full of bluesy piano and bright guitar strumming. The chorus has many background layers that accompany Young’s classic vocal to make for a full-sounding, slightly more upbeat vibe. 

When K.D Lang covered it in 2008, she offered a rich, powerful tribute to the song. With her unmatched vocal ability and string accompaniment pulling on the heartstrings, this cover is unbeatable. She has such a pure tone and captivating cadence to her singing that makes this cover emotional and inspiring. 

You can find all of these covers and (a few more that didn’t make this list), in this playlist on Spotify. Let’s hope 2025 brings us some new heartbreaking covers!

Emily is a fifth-year Philosophy Major with a Minor in Professional Writing and Non-fiction. She loves playing music, playing soccer, and writing in her free time. She has lived in Victoria for 5 years now, and has always loved the perfect city-to-nature ratio.

She loved writing poetry and music when she was a kid, and dabbled in short fiction pieces. She got into journalism because she loves storytelling and collaboration with others. Her favourite parts of journalism are interviewing people, writing a story, and the overall connection to the community.