We've all spent time with hundreds of sad songs throughout our listening lives and in researching my new book, This Will End In Tears: The Miserabilist Guide to Music [It Books, $16.99], I found that people tend to be aggressive in defense of the heart-wrenching power of their favorites melancholic tunes.
My book ends with a list of the top 100 saddest songs, which stands as a culmination of the book as a whole. In it rests the sum of the hundreds of hours I spent listening to the saddest music in the world. I pulled from all genres--jazz, rock, classical, country, etc.--and across six centuries, and to avoid a list dominated by Leonard Cohen, Billie Holiday, Elliott Smith, and Townes Van Zandt I stuck to a one-song-per-artist rule. Historical import, crowd-sourcing, straw polls, and my own listening, contemplating, listening again, and second-guessing were all factored into my decision making process.
Here, for argument, applause, and derision, is an excerpt, the tip of the iceberg, of my top 100 saddest songs ever.
Written by American composer Samuel Barber while on a retreat in Venice, the "Adagio for Strings" has become the international sound of sadness. It was first performed by the NBC Orchestra under the baton of Arturo Toscannini in 1938 and was played by shocked radio broadcasters following the unexpected death of President Franklin D. Roosevelt in April 1945. It has since been used in numerous public funerals, was a pivotal aspect of Oliver Stone's 1986 film, <em>Platoon,</em> and could be heard everywhere following the events of September 11, 2001. In 2004 it was named the saddest song ever in a BBC poll.
Written by Jewish high school teacher Abel Meeropol and definitively performed by Billie Holiday--though the song was not written for the singer as she liked to claim--there is no stronger condemnation of the sadness and horror of bigotry in song than "Strange Fruit." The unforgiving imagery of "bulging eyes" and "twisted mouth" sets up the palpably unsettling dichotomy between fruit and flesh that plays out in the final verse as the crows descend, the rain falls, and the sun rots a "strange and bitter crop."
The most modern of John Dowland's Elizabethan lute songs, one can easily draw the line from "In Darkness Let Me Dwell" to every modern master of gloom. One of Leonard Cohen's myriad nicknames may be "the Godfather of Gloom," but that title rightly belongs to Dowland.
Townes Van Zandt wrote more than his fair share of gentle heartbreakers, but the simple narrative of "Marie" is spun from so much tragedy that it is often in danger of toppling into farce. The story of a homeless and broke rail worker who meets a woman he loves, attempts to find her food and clothing, gets her pregnant ("In my heart I know it's a little boy / Hope he don't end up like me"), and then wakes up one spring morning to find her dead ("my little boy safe inside") is performed by Van Zandt with such plainspoken despair it makes the world he paints seem nearer and more real than most have ever imagined it could be.
Written by the prolific and now oft-forgotten gospel songwriter Albert E. Brumley--apocryphally credited with composing some 800 songs in his lifetime--"Rank Stranger" was first published in 1942 under the title, "Rank Stranger to Me," and may arguably be the most lugubriously evocative song to address the old adage, "you can never go home again" ever cut into acetate. First recorded by the Stanley Brothers in 1960 the song relates a simple bluegrass ballad of a man returning to his "home in the mountains" only to find that everyone he knows--including his "mother and dad" and all his friends--have passed away and are waiting for him "by the bright crystal sea." The song remains one of the Stanley Brothers' most popular and in 2008 their 1960 recording was added to the National Recording Register.
Johnny Cash once told Bob Dylan that it was the saddest song he'd ever heard and artists as diverse as Ray Charles, Dean Martin, Cassandra Wilson, Diamanda Galás, and the Mountain Goats, among many others, have recorded it, but "I'm So Lonesome I Could Cry" wasn't even originally intended to be a song, per se, rather it was earmarked by Williams to be one of the more obscure recitations of his alter ego, Luke the Drifter. Nervous that the imagery and metaphors of the lyric would be too pretentious for his audience Williams tried the song out on his band, which enthusiastically suggested he record it, which he did. Williams would later note it as his personal favorite, though when it was released in 1949 it appeared as a B-Side to the decidedly more prosaic, "My Bucket's Got a Hole In It," perhaps his concerns over its lyric use of language not completely calmed. The original recording is a masterpiece, but it's the surprisingly slower live recording captured during one of Williams' Mother's best performances--officially released for the first time in 2008--that best serves the song's lugubrious sentiment.
The Chairman of the Board devoted much of his mature career to plumbing the depths of loneliness, heartbreak, and regret and its arguable that no song captures Sinatra's late-night emptiness as "Only the Lonely" does. Written by Sammy Cahn and Jimmy Van Heusen specifically for the singer, and given a consoling arrangement by Nelson Riddle, Sinatra squeezes every bit of pathos from the lyrics, and as he recalls "picnics at the beach when love was new" and philosophizes from his bar-side lectern that the "hopeless little dream" of love may only come but once, there's no denying he believes every word.
"Nothing Compares 2 U" was initially written by Prince for the Minneapolis band The Family, and first appeared in 1985 on their lone eponymous album, but when Sinead O'Connor chose to include it on her 1990 album, I Do Not Want What I Haven't Got, she took full possession of the song, infusing it with an inconsolable heartsickness born of her own emotional turmoil. A video that featured little more than a close-up of O'Connor's face as she sings--and a pair of unplanned tears shed in the final verse--helped the song reach number one in pretty much every country in the Western Hemisphere, while Pitchfork has since placed it at #37 in their list of the Top 200 Tracks of the '90s and Rolling Stone placed it at #165 in their 2010 Greatest Songs of All Time list.
Is there any more gorgeously rueful monument to lost innocence in pop music than "Caroline, No," or any line more heartbreakingly breathtaking as Brian Wilson's confessional, "It's so sad to watch a sweet thing die"? Originally released as a Brian Wilson solo single in March 1966 (it stalled at #32), before appearing weeks later as the final track on the Beach Boys seminal Pet Sounds album, "Caroline, No" features only Brian Wilson on vocals, who had original titled the song "Carol, I Know," but after lyricist Tony Asher--whose girlfriend had recently moved to New York and cut her hair, providing inspiration for the song's opening lines--misheard it as "Caroline No" the pair decided to keep the new title. The song's coda--Brian's dogs, Banana and Louie, barking at a passing train--gives the song's sense of loss additional depth. In a 1989 interview Wilson said that the song reflects the feeling that "once you've fucked up, or once you've run the gamut with a chick, there's no way to get it back," concluding the sentiment by saying, "I just felt sad, so I wrote a sad song."
A 21st century lament born beneath the furling, black dust clouds that drifted from lower Manhattan on 9/11 and the proceeding days, "DLP 1.1" blots itself into being in a cycle of destruction that takes just over an hour. It is the sound of a mechanical heartbeat crawling to a stop, the breath slowly seeping from the speakers; the sound of technology giving into its own obsolescence, removing itself from the equation; and it's the sound of America's sorrow in the face of her lost innocence and naiveté. "DLP 1.1" is built from a brief synthesizer loop of ponderous melancholy Basinski composed and captured on tape in the early 1980s. While transferring the tapes to digital sources in September 2001 (while the planes were hitting the towers) the composer found that the old, analog ribbons were eroding and chose to create a new piece based on their deterioration: As the loop plays the tape decays and the solemn, pastoral melody degrades into silence.
She was the sound of post-war America, the sweet voice of America's spread to the suburbs ("The Doggie In the Window"), but Patti Page's 1950 rendition of the Redd Stewart/Pee Wee King country standard, "Tennessee Waltz"--first recorded in 1947 by Cowboy Copas and initially pegged as a B-Side for Page's novelty song, "Boogie Woogie Santa Claus"--has sold 10 million copies making it both the biggest selling single by a female artist and the best selling country music song of all time. The simplicity of the song is not lost on Page: "Someone introduces their boyfriend to someone else, and now he's no longer her boyfriend. It's just a sad love song," but the simplicity is what makes it so heartbreaking as she relives the memory in perpetuity, recalling clearly the waltz burned into her memory, reminding herself over and over of "just how much I have lost."