Definitely Steven Seagal in that reggae song he did. This one.

https://www.youtube.com/watch?v=3v4-zYghodc

Tom DeLonge : Blink-182

Never hit right for me. Terrible voice. Nasally and whiny. Wanna be punk. Men in their mid to late 20s singing about the drama only a 15-year-old in high school would care about or experience. It was weird.

I had no issue with Billie Joe Armstrong and Greenday. I really enjoyed their career and catalog.

Someone I know listens exclusively to the Beatles on the car radio. From all the Beatles hype, it should feel like a party, but instead it feels like you're listening to jingle commercials during the whole ride.

Really surprised that no one's mentioned Yoko Ono.

Corey Feldman's Angelic 2 the Core is without a doubt the worst album I've ever listened to. It is not just mediocre or underwhelming, it is not just a "miss," it is actively and unforgettably horrible. Definitely worth checking out.

I posted it in reply to another comment, but I think this is worth it's own mention.

Puddle of Mud - About a Girl, live on Sirius

Easily the lead singer of Kings of Leon. That whine in his voice makes me want to chug bleach.

The worst recorded sound that I have ever heard was Kurt Cobain doing a mic check on a Nirvana live bootleg. Like a tortured cat with laryngitis.

Trout Mask Replica by Captain Beefheart and his Magic Band. It's essentially unlistenable.

Red Hot Chili Peppers, best band ever, but boy is Kiedis a bad vocalist. Kudos perhaps for not doing auto tune.

Fleas energy made up for it and the songs are all bangers so it kind of pushed you over it. But if you keep focused on the vocals it's shit.

Smashmouth

Anyone remember The Fall?

Rest in peace, Mark E Smith, but fucking hell that was awful, but in a brilliant way

Thanks man

David Lee Roth’s solo work… makes my ears bleed

Linkin Park and Papa Roach. 2 okISH bands with the worst singers in music history. Shit gives me headaches.

The Shaggs, but I enjoy them anyway.

David Lee Roth. Tone deaf

Scruffy the cat.

Just the shittiest music. They were bad enough that despite it being over thirty years since the single listen I had of the one album I had, they still stand out for being bad.

Rebecca Black.

Freespirit Graham.

My father used to book acts for a local club, and this guy played there once. He was awful. There's no nice way to say it, he just really wasn't very good. He played and sang songs that nobody recognised, and did it badly. To make things worse, he was paid, but went around with his hat at the end of the set asking people for money. Needless to say, he didn't get a good reception.

About a year or so later, my father booked another singer, and it was the same guy going under a different name. The music night was popular, so there was a decent sized crowd already there when he walked in, and quite a few of them remembered him. My father asked him what he was doing there, and he said that he thought it was worth a try.

He was told to leave without playing, as the people who remembered him were already annoyed, and weren't the type of people to suffer a fool kindly.

When I heard the Tool cover of No Quarter and found out the original was by Led Zeppelin I gave that version a spin too. My disappointment was immeasurable and my day was ruined.

Reason being that I really like the Led Zeppelin vocalist. But his performance on that song is just unbearable to me.

The Tool cover though, absolutely amazing!

Florence Foster Jenkins singing the Queen of the Night's aria.

Can't stand the voice on Matt Bellamy from Muse. I could probably tolerate them with a different singer.

Imagine dragons - cutthroat. I dislike imagine dragons as it is, but this song is so bad it sounds like a bad parody of a shitty song.

(FYI, I hold different views than this instance)

TL;DR: for me it's current russian warsongs and covers of 80-90s classics that put the opposite meaning into them. Polina Gagarina, Shaman are the most known artists due to being banned from YT, but there are dozens of them. What and why - I'd try to explain in following paragraphs.

They don't feel either inspired or honest, most of the worthy artists don't want that mark in their resume so it's left either for newbie artists or oldies who fear they are losing relevance. The western-in-everything 'Я русский' is the only catchy tune local media empires could produce, others are even more cringe like '333', they don't even compare to what repressed guys did and do.

Surprisingly, the same notion is shared with my relatives who do support the war (unlike me) or at least our men there. We still have a tradition of singing along the songs of old over the table when we meet with our elders, or over the fire if camping or meeting in the countryside, mostly soviet songs with inclusion of 90-00s. And itso happens there's none of the promoted ones in the menu.

But that also tracks with the concerts on the TV we sometimes put on. It's all older stuff by mostly aging artists. The contemporary russian music culture, as I suppose, was castrated by some sort of negative selection and I can't think otherwise.

And what is really embarassing for me personally to hear is appropriation of songs that are either anti-war or asking for changes (namely KINO's ones) sang in this day and this year by those who support both the regime and the war on state TV. That's like this one republican guy just one hair width from discovering what RatM's songs are about. There's some second-hand shame you want to wash off in a bathroom right after hearing.

Worst concert, REM when they were starting out.

Recorded voice that irritates me the most? Dead Kennedys.

I am, personally, pretty tolerant of imperfect singing if the song is good, think a whole lot of bands just let the best singer they have sing, instead of finding someone who can really sing, and that's OK.

Guns and Roses in '91 or so. God I loved them so, every song. When we got a chance to see them in OKC, with some band I'd never heard of, Crashing Gourds?, something like that.

We were tripping acid and the crowd was wild, should have been fun. They came out 2-hours late, screamed shit into the microphone, beat their instruments and left. Sometimes I couldn't even tell which song they were playing, that bad.

And worse, the opening band, who later became wildly popular, was apparently booed. We were late and had missed them.

Calum Scott easily. That one song that kept playing during every commercial break drove me to madness. It's that "You Are The Reason" song that Kay Jewellers used for one of their commercials, and my God it was the most overplayed shit in the universe while it was still airing and made me despise that song. I hated the sappiness and I hated the stupid-ass high pitch he would constantly sing in throughout the whole song. It's the one and only Calum Scott song I listened to. Kay Jewellers always picked the worst and most ear-piecing sappy songs for their commercials. I have never listened to another one of his songs, and I don't plan on ever doing it. Song is nothing but him sounding like a pussy who cries and whines around woman trying to get them to like him. And keep in mind, this was on every day, on every commercial break. I could never go even ONE DAY without hearing that effing song on my Roku. I was, at one point, seriously contemplating ripping my ears out if I ever heard it on my TV again.

Hearing that song practically every single day on every goddamn commercial break made me unbelievably angry. Thank God Kay have stopped playing the commercial with that song included, it drove me absolutely insane every time I heard it on a commercial break. I got sick and tired of hearing it very quickly. Sometimes, it would get so overplayed in one day that I wished I was deaf on numerous occasions. That song has just turned me away from the artist entirely as I bet all of his songs are cringeworthy, sappy songs with him singing in an ear-splitting high pitch. "You Are The Reason" is a full-blown assault on the ears.

Never listening to another one of his songs again after that. One of his songs was bad enough.

And here's the commercial if you are wondering: https://www.youtube.com/watch?v=2Tu_eMQuKGk

My answer may not quite fit the topic. But I'll share anyway.

In the late 20-teens, ZZ Top and John Fogerty we're touring together. My wife and I saw them on the Jersey Shore (thanks VetTix!) and Fogerty opened the show and absolutely killed it. Then ZZ Top played and Billy Gibbons just didn't have it anymore. We left early.

Several weeks later they played Jones Beach Amphitheatre and thanks to VetTix we got to go again. Once again Fogerty knocked it out of the park and Billy was just not up to snuff.

It was sad.

Interestingly, Billy Gibbons is featured on one of the tracks of Slash's new album Orgy of the Damned. That track is the perfect fit for Gibbons and it holds together beautifully.

Not quite the answer to your question, but Cafe Tacvba. Great music, lousy singer, like that guy says about Red Hot Chili Peppers. Jesus Christ.