10 insane musical collaborations that shouldn’t have worked

Musical chemistry is a bit of a funny thing. As much as people can spend their time honing their craft, some of the most no-brainer musical team-ups can fall apart if they don’t have the right idea behind them.

But as bands like Linkin Park figured out, nothing was impossible if everyone simply had the right skills, talent, and motivation to see a project through to the end.

Then again, some of the biggest rock and roll bands of all time are usually about sticking to one genre. Not everyone wants to stretch themselves every time they go into the studio, but when some of the biggest names in music end up taking one step out of their comfort zone, it can turn into absolute magic when they start speaking the same language and manage to find some common ground in between their material.

After all, rock is descended from blues half the time, so any genre from R&B to rap to soul music could fit under that umbrella, and some of the greatest moments in an artist’ career come when they are working out different pieces of their sound that they don’t even realise are going to be classic until they show it to the rest of the world.

While some of these songs are definitely an acquired taste, it’s insane to think that bands and artists that make about as much sense as combining orange juice and toothpaste managed to mesh like peanut butter and jelly. The universe seemed to point to everything about their tracks going wrong, but after putting their foot down, each song here stubbornly refuses to do anything else but kick ass.

10 musical collaborations that shouldn’t have worked:

‘Forever’ – Kiss and Michael Bolton

Kiss - Band - Far Out Magazine

Kiss never seemed to do anything that was meant to be low-key and easy listening. Even on their greatest ballads, everyone from Peter Criss to Paul Stanley made sure everything hit like a slap in the face whenever someone heard one of their tunes. But even by the logic they were working with in their makeup-less era, the thought of using one of the cheesiest crooners in the world of soft rock was a bit of a stretch.

That’s not to say Michael Bolton didn’t have talent as a vocalist. After all, he started trying to sing for a metal band before becoming one of the biggest balladeers of the late 1980s, but sprinkling his touch across the song ‘Forever’ is absolutely perfect. Stanley’s voice wasn’t all that far off from what Bolton was doing at the time when he was singing his hard-rocking, so once Bruce Kulick added the right solo to everything, it started to feel closer to a Kiss song than anything too syrupy.

And while Kiss has been pretty democratic over who sings what throughout their discography, we should all be counting our blessings that Gene Simmons never got hold of this song. Because as well as he pulls off the demon persona, there was no way that slimy voice would ever pull off an earnest ballad like this.

‘Home’ – Bone Thugz-n-Harmony and Phil Collins

Phil Collins - 1989

Any rapper who chooses to use a pop singer on their song needs to know what they’re getting into. It would be easy to cosign someone because they have an ear for hooks, but as evidenced by the many hip-hop artists who put their blind faith in Maroon 5, not everything works out the same way with every pop singer. But still, how did Phil Collins, known both then and now as one of the most middle-of-the-road pop singers, manage to hop on a hip-hop record and get away clean?

Well, first of all, let’s get one thing out of the way about Collins: he can be funky as hell when he wants to. A lot of those Genesis rhythms aren’t exactly easy to play, but listening through his solo career, he had a healthy dose of soul and R&B in hismusical diet, so ‘Take Me Home’ felt like the perfect backdrop for Bone Thugz-n-Harmony here, even if Collins’s vocal does seemingly come out of nowhere when he comes blasting in on the chorus.

Then again, the rap collective is doing a fair bit of heavy lifting here, especially since their flow is about as sticky as any other singer’s cadence when they rapped. But thanks to everyone being on their best behaviour and Collins being cool enough to appear in the video for the song, the world has been gifted with some of the greatest rappers of the 1990s singing alongside someone who could have passed as someone who did their taxes had he not written ‘In the Air Tonight’.

‘Maad City’ – Kendrick Lamar and Imagine Dragons

Kendrick Lamar -2025 - Grammys 2025 - Recrod of The Year

The death knell for most bombastic rock music truly came when Imagine Dragons started to lose the plot a little bit. There are many great attributes to their style, but after leaning into the stadium-rock vibe and purging all kinds of guitars from their songs, there are many people who still feel they deserve a place next to Nickelback as the reason why people hate rock and roll nowadays. But if you’re someone with the size and scope of storytelling as Kendrick Lamar, you can put any instrumentation behind you and sound massive.

While K-Dot was already on the rise following the release of Good Kid Maad City, his choice to perform with Imagine Dragons at the Grammys had the potential to be either earth-shattering or a terrible mistake. If there’s one thing that the rock band knows how to do, though, it’s bring the rhythm like nobody else, and getting that percussive smack to Lamar right as the beat drops on the song is the perfect blend of rock and hip-hop that no one realised they wanted until they saw it in context.

And after nu-metal left a bad taste in everyone’s mouth by the turn of the millennium, having Lamar work so seamlessly off of Imagine Dragons makes it sound like the genre hasn’t breathed its last breath yet. There’s room for rap and rock to still intermingle, and given how the Compton rapper was able to freestyle over a Prince song when he arrived at Paisley Park, the door is still open for him to bring more guitars into the mix.

‘Black Gives Way to Blue’ – Elton John and Alice in Chains

Jerry Cantrell - Alice In Chains - Guitarist - Musician - 2010

The entire mindset beyond the Seattle music scene was much different from what anyone else had ever experienced before. Whereas everyone in New York and LA were trying to outdo the person next to them and find ways to make inroads to new sounds, it wasn’t out of the question to see everyone from Soundgarden to Melvins propping each other up in support of whatever their friends were doing. After all, there was no chance that they would get famous, but one that started to change, Alice in Chains had some other plans for how to stage their comeback.

They could have easily brought in some fantastic string sections like they did on ‘I Stay Away’ for ‘Black Gives Way to Blue’, but having Elton John play the keys was a much better way of showing their roots. Jerry Cantrell was always a tremendous fan of John’s music growing up, so having him on one of his records made it feel like everything came full circle, especially when paying tribute to the memory of Layne Staley.

To his credit, John seemed to understand what the band was going for perfectly, making his performance almost sound like a musical box with a slightly twisted angle during the chorus. It has a lot of beauty behind it, but like all good Alice in Chains, it has a tortured element that makes it both depressing and inviting.

<em>Foreverly- </em>Billie Joe Armstrong and Norah Jones

Billie Joe Armstrong - Green Day - 1997 - Good Riddance Time of Your Life video

Billie Joe Armstrong never claimed to be a snob regarding music. There were punk purists out there who may have roasted him for listening to The Beatles, but as far as he was concerned, good melodies transcend any kind of hangups that someone might have with a particular genre of music. He could appreciate a good metal song and a pop masterpiece, but folk-tinged country tunes were the last thing on people’s minds when he started working with Norah Jones.

While the idea of putting together an Everly Brothers tribute album fits snuggly into Jones’s wheelhouse, Armstrong is a great companion when singing some of these tunes. They’re nowhere near the same level as the Everly Brothers were in their prime, but Armstrong’s slightly nasal delivery does have that kind of youthful exuberance that works just as well for country music as it does when he’s singing ‘Basket Case’.

Even when going into his later career, Armstrong did take a few tricks from working on this album as well, eventually having the confidence to make a song like ‘Ordinary World’ on Revolution Radio. Breaking out this kind of song might have been one of the least punk things he could have done then, but Armstrong wasn’t looking to please anyone anymore. As long as he had a song in his heart, he would belt it out to the rafters whenever he had the chance.

‘The Wanderer’ – U2 and Johnny Cash

Bono - The Edge - U2 - 2023

U2 had barely figured out what they wanted to be throughout the 1990s. They clearly weren’t going to go back to The Joshua Tree now that grunge had taken over, but while Achtung Baby was a great record, you could tell they were pulling at their sound all the time, seeing what pieces fit and which ones didn’t. And despite being the mouthpiece and face of the band, the best moments from their next album came when they told Bono to get out of the vocal booth for a little bit.

While The Edge did a serviceable job playing the emotionless droning voice on ‘Numb’, having Johnny Cash close out the record was one of the most inspired, strange choices any band could have made at the time. Cash was only just beginning to break back into the industry with Rick Rubin, but since he saw the potential in a song like ‘One’, he knew that these Irish kids had a lot more going for them than making random glitchy noises in the studio for the rest of the record.

No, that kind of behaviour would be reserved for Pop, but for those few minutes listening to Cash speak-sing his way through this tune, it feels like two different worlds rubbing up next to each other in the perfect way. Bono may have been in over his head about many things in U2’s career, but if he could make a duet with Frank Sinatra and get away clean, why not try his hand at working with ‘The Man in Black’?

‘Kickapoo’ – Tenacious D and Ronnie James Dio

Jack Black - Tenacious D - 2024

Every comedy act tends to get put on the side in rock and roll. Spinal Tap was always going to be more of a punchline rather than an actual band, and no matter how many times Weird Al Yankovic made something genuinely great, there was no chance that people were going to look at him as some god of music by any stretch. That might have been how Tenacious D started, but how they got so many giants for The Pick of Destiny is still one of the greatest moves in comedy rock.

Although Dave Grohl adopts the role he was born to play as Satan at the very end of the movie, the overture of the film is a star-studded cast of characters in the first two minutes. Outside of the stunning performance by Jack Black, having Meat Loaf play his disciplinary father before Ronnie James Dio gives him the determination to move to Los Angeles rocks so much harder than a band that’s primarily known for spouting out as many dick jokes as possible.

More than anything, though, this tune highlights the kind of vocalist that Black can be, even managing to match his duet partner’s intensity in a handful of places. The Pick of Destiny could easily have been a send-up of all other rock origin stories, but within four minutes, Black and Dio managed to craft a song that could stand alongside any other concept album overture from years gone by.

‘Numb/Encore/Yesterday’ – Linkin Park, Jay-Z, and Paul McCartney

Linkin Park - Full Band - 2010s

There was no reason to believe that Collision Course by Linkin Park wouldn’t be a slam dunk. The band had already begun working with hip-hop beats since they began, so getting one of the greatest rappers alive together for a project made too much sense once the beat of ‘Numb’ layered up perfectly with the backing track to ‘Encore’. But for as futuristic as Linkin Park could sound at times, you’d think they would be allergic to anything resembling classic rock.

And yet, during their massive performance with Jay-Z at the Grammys playing their mashup, closing things out singing ‘Yesterday’ with Paul McCartney is one of the strangest pairings anyone could have thought of. This was years before Macca thought working with Kanye West was a good idea, but what’s remarkable is how little anyone does to embarrass themselves here, especially Jay-Z, who makes his signature ad-libs in between lines fit next to McCartney’s tried-and-true voice.

The clean tone in Chester Bennington’s voice may have been explored a bit more when making the album Minutes to Midnight, but there was no reason to think they couldn’t keep this momentum going. There are a lot of great moments in this tune, but it hits that nice sweet spot where it’s a bit more current than what the oldheads are into and not too saccharine for the nu-metal crowd.

‘Don’t Hurt Yourself’ – Beyonce and Jack White

Beyonce - 2023 - Raph Pour-Hashemi

By the time the production of Lemonade started, Beyoncé was out for blood. The idea of Jay-Z cheating on her was one thing, but if there was any way for her to channel that anger into song, she wanted to make sure that he didn’t know what hit him when she entered the studio. She was going to go all over the map, but getting one of the kings of garage rock may have been a bit of a reach.

While Jack White was known for making something much more abrasive, having the song ride in on a drum sample from ‘When the Levee Breaks’ is the perfect introduction for Queen Bey to put someone in their place. And since both this song and the entire album rely on processing grief and letting out one’s grievances with the world, it made all the sense to someone that was steeped in the blues, with White making his guitar sound like it’s short-circuiting, crying and laughing all at the same time.

Even though the album does play out like Beyoncé going through the stages of grief before finally forgiving her husband, it was completely understandable if Mr Carter wanted to run away after this tune. Because when you have this kind of backing behind you, anyone who gets in your way will be leaving in a body bag.

‘DoYaThing’ – Gorillaz, Andre 3000 and James Murphy

When Converse began their line of singles, the whole thing felt like a complete novelty. Getting a bunch of different artists together in a room for a single, most of which need to be made from scratch, and it’s for a shoe company? Just reading that premise sounds like a recipe for disaster, so how on Earth did we manage to get one of the best songs from three different legends of 2000s music?

Well, it all comes from knowing the Gorillaz world. Damon Albarn always wanted the band to be elastic in some way, but bringing in the stuttering vocal style of James Murphy works surprisingly well against 2D’s lethargic vocals. But the real star of the show here is Andre 3000. It was clear that new solo music was out of the question at this point, but in one verse, he laid down one of the greatest flows that he ever came up with, which is saying something considering how well he opened up ‘Bombs Over Baghdad’.

And while the extended versions fell like it could have been made for laughs, hearing ‘3 Stacks get more and more unhinged saying ‘I’M THE SHIT’ makes him sound like he’s about to have a mental breakdown in the booth if the song went on any longer. This kind of song almost feels like it’s not meant for this world, but in the crazy world of Gorillaz lore, it might as well be another Tuesday.

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