Debates over whether Madonna is a great singer have floated around her for decades — her voice is too thin, her sinking into the low notes on ballads like “Live to Tell” too uncertain. But she’s undoubtedly one of the best straight-up performers that has ever graced top-40 radio, making up for any vocal deficits with the Whitneys and Mariahs of her various pop eras by putting her up-yours personality front and center while culture-vulturing her way toward the cutting edge. (The Internet appropriation machine caught up with her in the late ’00s, but she held out admirably long.) A chameleonic performer who could play the teen-on-the-verge of “Papa Don’t Preach” as effortlessly as she could portray the sternly sexual Mistress Dita on Erotica, Madonna’s ability to push pop forward through sheer force of will transformed the game. –Maura Johnston
89. Ronnie James Dio
Ronnie James Dio had that badass wail that’s made for karaoke goers to fail miserably at recreating, but that’s just one part of his appeal. Up until recently, people overlooked that he replaced Ozzy in Black Sabbath and that some of his records are better than Ozzy’s. Dio allowed Tony Iommi to open up his guitar playing into new melodic dimensions, helping break out from the more blues-based blocks he was in with Ozzy. He helped Sabbath make actual ballads, with “Die Young” and “The Sign of the Southern Cross” really showing off his mix of confidence and sensitivity.
Dio got his start in a group called The Vegas Kings, and that bygone era of showmanship was part of his stage presence throughout his career. Thanking an audience at a show is pretty rote, but his graciousness made it sincere that he, a Metal God, was thankful to you personally that you came to see him. On stage and off, he served as a guiding light for lost youth and youths-at-heart, never skipping on the inspiration. Dio’s awesome vocal power wasn’t tempered by his humility and warmth; they made him a relatable inspiration while maintaining a clear sense of leadership. There’s no “I” in metal, but there is “We” in “We Rock”. –Andy O’Connor
88. Ian Curtis
Ian Curtis went to a different place when he performed, but it took him a little while to get there. This was part of the thrill of Joy Division: watching Curtis close his eyes and retreat awkwardly into himself, then watching an arm begin to move, then flail, then watching both legs do the same. And then, suddenly, the formerly stoic frontman had completed his transformation into a blur of sound and movement. Though he possessed one of the deepest voices in punk, Curtis sang like the stakes were impossibly, unfathomably high. “Dance, dance, dance to the radio!” sounded less like a good time and more like a shadowy tidal wave about to consume the world. It sounded lonely. And that’s what made Curtis such an alluring vocalist and frontman — despite his bandmates up there with him on stage, he existed in an empty space of his own creation for two to three minutes at a time. –Collin Brennan
87. Van Morrison
There’s something special inside of Van Morrison’s voice. Greil Marcus once opined, “His music can be heard as an attempt to surrender to the yarragh, or to make it surrender to him.” The yarragh is a term that was originally coined by the Irish tenor John McCormack, and as Marcus defined it, it’s a “voice that strikes a note so exalted you can’t believe a mere human being is responsible for it.” Listen to songs like “Caravan”, “Into the Mystic”, or “Madame George”, and you’ll know it instinctively.
At the beginning of his career in the mid-‘60s, while he was still fronting the Them and bashing out singles like “Gloria”, “Baby Please Don’t Go”, and Here Comes the Night”, Morrison adopted a caustic, rapid-fire delivery that matched the frenetic pace of the music. It was only once he struck out on his own, slowed things down, and dove headlong into the sounds of blues and jazz that the full breadth of his emotive instrument revealed itself. On masterpieces like Astral Weeks and Moondance, he stopped chasing the songs and bent the music itself to the shape of his voice. As a performer, he lives inside the song. He breathes in the notes and exhales all the emotion of the universe. –Corbin Reiff
86. Ann Wilson
The inimitable Ann Wilson’s entryway into music stardom is immortalized in one of Heart’s most memorable tunes, “Magic Man”. At the time, Wilson says she was “existing in this very staid, suburban state of being” at home until she met the band’s Mike Fisher (her magic man). Wilson left home and went to Canada, joining Heart in the process. It’s a good thing she followed that path towards music: Wilson, along with her sister Nancy, took over the pop charts in the ‘70s with their dynamic, throttling rock songs that seemed to come with a distinct strut of their own.
Famously, Ann never had formal musical training before she took over as the lead singer of Heart — even more of a testament to her natural talent, given how potent and clear her voice is (check out how far away she holds the microphone in this performance of “Crazy on You”). Earlier this year, Us Weekly asked Wilson to give them a primer on how to hit those tough high notes. Her response? To not be “wimpy.” As for tips on how to be a rock star, which Wilson embodies in the 1977 video for “Barracuda”? That can’t be taught, only known. –Paula Mejia
85. Joe Strummer
On the surface, it doesn’t seem that hard to be a punk singer. As an art form rooted in anti-establishment values and clear, unfiltered expression, the genre necessitates a total lack of pretense, and by extension, an aversion to showmanship. Keeping in tune, staying in time, striking a pleasant tone — these are the cornerstones of the musical status quo, and accordingly, the trappings of punk’s very antithesis.
With the rise of The Clash, however, we saw that these two spheres — the melodic and the malcontent — could co-exist. Consider Joe Strummer, then, not a frontman, but an ambassador, the rebels’ Trojan Horse. Sure, his cockney crows are hardly Eurovision worthy — his winded style belies a lack of technical training, not to mention a barely controlled anger. But it’s that imperfection, that relatability, that transformed the dressed-down, rudimentary hooks of “I Fought The Law”, “Should I Stay or Should I Go”, “London Calling”, and so many others into global rallying cries. –Zoe Camp
84. Joanna Newsom
Sometimes you’re gifted with a voice unlike anyone else’s — and people tease you because it’s so out there. It’s an understatement to say Joanna Newsom sings unlike anyone else. Usually on first listen, people hesitate to comment. Is that how she actually sings? How old is she? Does she hear what she sounds like? It’s easy to mock her singing style on “Peach Plum Pear”, a delivery reminiscent of Kate Bush and other “weird” singers, but her pointed jabs hit out of left field. If people didn’t know better, her voice could be mistaken for a child’s playful song recorded in jest. No one knows if that’s a good thing.
But since her 2004 debut, The Milk-Eyed Mender, Joanna Newsom’s vocal delivery has changed. Those yappy childlike notes and shrill pitches appeared on Ys with “Monkey and Bear”, but she cooed them. The note shifts became graceful on Have One on Me, softening into a cozy yawn on “Baby Birch”. Then, on 2015’s Divers, she found full-blown maturity, rephrasing her vocal delivery into a style that deepened its valleys and took on operatic softness with “Time, As a Symptom”, in part because of vocal cord nodules she developed in 2009 that left her unable to speak for two months. No matter how many people cite her singing as an example of obnoxious delivery, there will always be twice as many fans ready to defend her.
After all, Joanna Newsom is able to leap across notes with unexpected grace, her ability to engage with the storytelling all the more apparent and, when it comes down to it, successful, giving listeners plenty to trace in awe on no matter how many times they’ve heard a song. –Nina Corcoran
83. Paul Simon
Not every singer loves the sensation of holding long notes in their throat; Paul Simon, for example, seems to like the texture of words in his mouth. You can hear it on the “who” in “Me and Julio Down by the Schoolyard”; the bouncy ‘b’ of “Bone-digger” on “You Can Call Me Al”; or in the way he revs into the ‘r’ for “You don’t need to be coy, Roy,” on “50 Ways To Leave Your Lover”.
This wasn’t always the case. Along with his partner and frenemy Art Garfunkel, he was among the most successful purveyors of folk rock in the ‘60s. Those simple, haunting songs made Simon & Garfunkel icons in the counterculture movement. But for his solo career (and before our society had coined the phrase “cultural appropriation”), Paul Simon’s curiosity about the music of other cultures allowed him to reinvent pop music with sounds from the other side of the globe. Now at 75 years old, he’s got more tricks than ever in his “big bag of sounds,” and many think his 2016 album, Stranger to Stranger, is his best effort since Graceland. Just listen to the way he chews on “My man” from “Wristband”. The man is still having fun. –Wren Graves
82. Leonard Cohen
An unspoken necessity to be included in this list was that a vocalist needed to have an entirely unique style, something that made them unlike any other singer. When he first debuted on the scene, it wasn’t that no one could sing like Leonard Cohen, but rather that no one did. Lines would tumble out of his mouth, flat and straightforward, giving the simplest modulations in his tone massive impact. There was less showmanship and more raw honesty, his exquisite poetry and broken-hearted love stories delivered deftly and simply. As decades passed, his baritone dipped and resonated, deepening as the Canadian singer-songwriter grew in age and wisdom rather than suffering. Cohen may be better known as a writer (particularly for giving the world and Jeff Buckley “Hallelujah”), but his voice is equally worth celebrating. –Adam Kivel
81. Joe Cocker
Joe Cocker sings like a man who spent a year doing nothing but gargling hot, liquid asphalt. He sounds like a man who smoked four packs a day from the time he was a five-year-old. He sounds like a man who passed on whisky and went straight for the kerosene instead. Cocker’s voice is not “pretty” in the traditional sense, but it’s extraordinarily, almost supernaturally powerful.
It’s easy to get lost in Cocker’s imitable gravely delivery, but it would be for nothing without the soul underneath. The reason why his version of “With a Little Help from My Friends” is so much more effective than the Ringo-sung Beatles original has everything to do with his instinct for where the heart of the song lies. In Ringo’s hands, it’s a quaint pop song about his friend’s ability to lift him out of a lovelorn funk. In Cocker’s, it becomes about the pain itself. You can hear his world falling apart around him through his wails of agony. It’s as thrilling as it is chilling. It’s the difference between singing about something and embodying the emotion itself. –Corbin Reiff