It’s finally here: Frank Ocean’s second album ‘Blonde’. Image: Highsnobiety
The sad boy is hardly a new concept in music, and while exact definitions vary from person to person, there is one rule in which everyone can agree on: in order to truly be a sad boy, one must possess pride in their sorrow. Musically, this presents itself in the form of deeply emotional lyrics that portray a softer and more vulnerable side to masculinity.
Though the modern-day sad boy lives with a freedom to express his unhappiness as much or as little as he desires, the movement’s predecessors were not afforded with such liberties. In fact, more often than not the forefathers of sadness were relegated to performing their misery in the key of indie rock. The mere notion of emotionally charged hip hop probably would have left N.W.A and Public Enemy in a fit of laughter. Times have changed though, and today’s pop culture has embraced the phenomenon, allowing it to appear across all genres and styles of music.
As a tribute to the timeless trend, we’ve rounded up a list of music’s 11 most iconic and revolutionary sad boys. So grab a box of Kleenex, put on your favourite Smiths record and try not to let that guy-liner smudge too much.
Morrissey, Images from coolmenhairstyle
Morrissey
Known globally as rock’s ultimate “sad bastard”, Morrissey has built a career around crafting melancholic indie and rock songs. This title, however, is the reason why many are incapable of recognising how much of a humorous genius he is, no matter how disturbing or dark his idea of a laugh may be. Unlike his goth contemporaries, Morrissey did not dress in smooth glossy leather jackets. Instead, he opted for baggy trousers and irregular jumpers – the original normcore uniform.
Suede (Brett Anderson on left)
Brett Anderson
As the frontman behind Suede, Brett Anderson became a Brit-pop icon for his androgynous look and heartfelt approach to songwriting. After the break-up of Suede, Anderson spent the early 2000s performing with his band The Tears, thus earning the award for ultimate sad boy band name.
Elliott Smith Live at silverlake lounge on 2001-02-06. Image: Youtube
Elliott Smith
With song titles such as “Miss Misery”, “Needle in the Hay” and “Everything’s OK” Steven Paul “Elliott” Smith won the hearts and tears of countless emo kids across the globe. Known for his distinctive whispery vocal style and lyrics about detachment, the singer songwriter even received an Oscar nomination for in 1998 for “Good Will Hunting”. And if that wasn’t enough to turn him into an indie legend, Smith’s fans have petitioned for a memorial park in LA ever since his controversial death in 2003.
Conor Oberst, image from stereogum.com
Bright Eyes
Before Conor Oberst’s transformation into the political cowboy we know today, he was singing about forlorn love and introducing albums with fake interviews on his brother’s death (also fake). Bright Eyes was a sad boy for The O.C. generation, giving awkward Seth Cohens everywhere something to listen to on their baby blue iPod minis.
The Postal Service, Image from MTV
The Postal Service
After the grunge movement of the ’90s, everyone kind of forgot that Seattle still had a music scene. Then, out of nowhere came the Postal Service, a side project created by Death Cab for Cutie member and 2003’s #1 sad boy Ben Gibbard. It’s been 13 years and we still get the feels whenever “Such Great Heights” comes on.
Casiotone For The Painfully Alone, Image from Metrolyrics
Casiotone For The Painfully Alone
The man behind Casiotone For The Painfully Alone — Owen Ashworth — is known for providing a musical representation of what the struggles attached with reaching mid-twenties feel like. Tiredness, frustration and sadness, are all common themes in Casiotone’s expressive bedroom-produced melodies. Many often accredit bands like MGMT, M83 or even The Postal Service as the pioneers of bedroom indie production, but we all know in our hearts that CFTPA made it all possible way before any of them.
Screenshot from Heartless music video
Kanye West
As most Yeezy fans are proud to affirm, 8o8s & Heartbreak was a game changer in hip hop. It ushered the genre to a whole new level, presenting the world with a rapper that wasn’t afraid of being emotional, especially after the untimely passing of his beloved mother Donda West. In fact, this music period in Kanye’s repertoire is commonly credited as the inspiration behind Drake and The Weeknd’s rise to fame.
Screenshot from Day ‘N’ Nite’s music video
Kid Cudi
When Kid Cudi joined the scene with Day ’N’ Nite, the song’s beats managed to effectively mask the somber lyrics for a short time. That is, until we collectively realised how dark it feels to chant “the pain is deep, a silent sleeper you won’t hear a peep” while on the dance floor.
Frank Ocean, Image from MTV
Frank Ocean
Known for providing palpable melancholy and grace through his vocals and passion, Frank Ocean is probably the most celebrated sad boy of our times. Ever since he revealed that many of his first album’s love songs were addressed to a man, the world of R&B and hip hop was shaken. His fans, however, respected and supported him throughout the struggle, and ever since he announced plans for another album, the world has been impatiently waiting for its release. We genuinely cannot wait for this sad boy’s gem to drop.
Nicolas Jaar, Image from the drake.ca
Nicolas Jaar
This contemporary sad boy has musical roots in New York City, where he made a name in the electronic music industry both as a solo artist and as a duo act with multi-instrumentalist Dave Harrington. His songs range from funeral-esque beats and vocals to experimental goosebumps-inducing records that grab hold and never let go. Jaar is the kind of sad boy that disappears whenever his music becomes “too known”, leaving fans across the globe on a constant hunt for the odd sign of life or two.
Yung Lean, Image from Highsnobiety
Yung Lean
Yung Lean is a Swedish rapper that quickly became a huge sensation throughout the world thanks in no small part to his online releases and distinctly Soundcloud fashion sense – bucket hats, Arizona iced tea and a random Japanese graphic for good measure. The post-internet aesthetic of this infamous musician has transcended the digital space and into the real world, making him a notorious prince of sadness born in cyberspace. He also has his own label named (you guessed it) – Sad Boys Entertainment.