Bob Dylan sounds like a cat in a garbage disposal and changed music forever. Here's my list of the so-called worst singers in history and what they actually teach us about making it.
 

There is something genuinely inspiring about a singer who cannot sing in any conventional sense making it anyway. It does not just give hope to the rest of us. It makes an argument about what music actually is and what it is actually for.

I am Tony Oso, a rock musician out of Melbourne, Florida. When I first started performing I was not exactly a finished product vocally. If you had heard some of those early shows you would have had opinions. But you get up, you do the work, and you find your voice by using it badly for a while first. That is how it works for almost everyone.

The inspiration for this piece came from watching Complete Unknown, a film that touches on Bob Dylan. Dylan is one of the most consequential songwriters in the history of American music and also a man whose voice has been compared to a wide variety of unpleasant things. It got me thinking about all the other artists who made it despite, or maybe because of, a voice that did not fit the standard mold.

Bob Dylan

This is where the list has to start. Dylan's voice has been described as nasal, as a whine, as a croak, as a cat stuck in a garbage disposal. He has been roasted for it for sixty years. He also won the Nobel Prize in Literature and wrote songs that changed how people thought about what a song could say and do.

The thing about Dylan is that his vocal delivery is inseparable from the power of his writing. When he sings Like a Rolling Stone the ragged quality of the voice is part of what makes the contempt in the lyric land. A polished voice would have sanded off exactly the edges that make the song work. You do not sing along to Dylan for the melody. You sing along for the poetry, and the poetry needed exactly that voice to carry it.

William Hung

She Bangs is burned into the collective memory of an entire generation of American Idol viewers. William Hung's audition was objectively off-key and objectively unforgettable. He became famous for it, took the attention seriously, and turned it into something. Most people who get fifteen minutes of fame spend it being embarrassed. Hung spent his making a record. That is a form of hustle worth acknowledging.

Yoko Ono

Yoko Ono is genuinely divisive and I think that is the point. Her experimental vocal approach, which includes things that most people would not call singing at all, is either visionary or unbearable depending on who you ask and on any given day sometimes both from the same person. What she figured out early is that avant-garde is a legitimate lane and that the goal is not to please everyone. The goal is to do something real. She did something real. The debate she generates is evidence of that, not a contradiction of it.

Fred Durst

Limp Bizkit fans are going to come for me and that is fine. Fred Durst's vocal range is genuinely limited. What he has instead is a specific kind of aggressive energy that translated perfectly into the nu-metal moment he was part of. Break Stuff works because of the delivery, not in spite of it. A technically proficient singer doing that song would have made it worse. Sometimes the voice that fits a song is the one that sounds like it means it, not the one that sounds pretty.

I have a complicated relationship with this one because I actually enjoy Limp Bizkit and I already made that case in my rap rock groups post. Fred Durst belongs on both lists simultaneously and I stand by that.

Lil Wayne

Lil Wayne is a legitimate lyrical genius who uses his singing voice in ways that are hard to defend on pure technical grounds. There is a lot of Auto-Tune involved. The vocal quality without processing is an acquired taste. None of that matters because the creative output is extraordinary and because he understood that the voice you have is the instrument you work with, not a limitation you apologize for. He never apologized for it.

Tom Waits

Tom Waits is a complicated entry because I do not actually think of him as a bad singer. His voice sounds like it was cured in a barrel of whiskey and left out in the elements for several decades, which is a specific aesthetic choice, not an absence of control. He sounds exactly like he intends to sound. The gravelly, weathered quality of that voice is what makes songs like Tom Traubert's Blues work as well as they do. A smooth voice singing those lyrics would be a category error. Waits belongs on this list as proof that the conventional definition of a good singing voice is narrower than it should be.

The Shaggs

Go listen to My Pal Foot Foot and then come back. I will wait.

Okay. What you just heard was three sisters from New Hampshire who were pulled out of school by their father to pursue a music career they had not asked for, with essentially no musical training. The result is something that sounds like it exists outside the normal rules of rhythm, melody, and time. And it became a cult classic. Frank Zappa called them better than the Beatles. Whether he meant it literally does not really matter. The point is that something about what they made connected with people who heard it, and technical proficiency had nothing to do with it.

What This List Is Actually About

The takeaway here is not that technical skill does not matter. It is that technical skill is one tool and not the only one. Personality, conviction, a specific and identifiable sound, the guts to get up and do it anyway, these things matter as much as range and pitch accuracy and sometimes more.

I have been developing my own voice for years across hundreds of live shows and a catalog of original songs. It is not a perfect voice. It is mine and I have learned to use it in ways that serve the music I am making. That process never really ends and I am not sure it is supposed to.

If you are an aspiring musician who has convinced yourself that your voice is the thing standing between you and making music, listen to this list again. Dylan made it. Waits made it. The Shaggs have a cult following. Your voice is already enough to start with.

You can hear where mine has landed after years of that process at tonyosomusic.com/music. Tears is probably the most vocally vulnerable thing I have put out and it is the song people connect with most. That is not a coincidence.