The Strangest (and Possibly Worst) Musical Collaborations Ever

Musical collaborations and “super groups” are both a blessing and a curse. Sometimes, they can bring us the joy and sense of triumph that comes when two artists are able to blend together so perfectly that it’s as if it were some sort of monogamous marriage. (Read about Jay-Z and Kanye West’s collaboration on Watch the Throne and watch the music video for “Otis.”) And sometimes, they just don’t stick. It’s like watching a little kid try to fit a square wooden peg in a round hole. It just doesn’t work, and it’s unapologetically sad. (Read about the ridiculous teaming up of Matt & Kim, Soulja Boy and Andrew W.K. and hear “I’m a Goner.”)

Since the release of the “I’m a Goner” single, and with the recent news that Bon Iver and James Blake will be working together on something called “Fall Creek Boys Choir”—too early to tell if that’s a song or an entire album—we present to you our 2011 music collaborations list.

Now don’t jump to the comment section just yet with rage at the presumption of the title of this list. This is primarily a list of the Strangest musical collaborations. Although, yes, some may be easily considered the worst . . . you decide.

1.
The Collaboration: Monsters of Folk
The Album: Monsters of Folk
The Problem: In 2009, Monsters of Folk was it. They were the “super group” of super groups for indie and folk music, featuring Jim James from My Morning Jacket, M. Ward from She & Him and his solo work, and Conor Oberst and Mike Mogis from Bright Eyes. We’re not looking at one particular song here, though, we’re looking at an entire album. And with that, there are some blow-out tracks we can thank to have today (take note of “Dear God (Sincerely M.O.F.)”). But when you get four highly popular and beloved musicians together for an album, you sort of expect the Traveling Wilburys of this day and age. Instead, you end up with a scattered and aimless record, tangled up in its own narcissistic “super-vision.”
The Video:

2.
The Collaboration: The Black Lips and GZA (from Wu-Tang Clan)
The Song: “The Drop I Hold”
The Problem: Here’s an idea: let’s take a really sloppy, DIY, lo-fi punk band and throw a verse from a disciplined Brooklyn rapper on the end of it. Whose manager fell asleep at the reigns for this one?
The Video:

3.
Collaboration: Bob Dylan and Kurtis Blow
Song: “Street Rock”
The Problem: Many people—from that kid on the street blasting Biggie in his ears to the English professor sitting behind dusty volumes of Shakespeare and Chaucer—might easily argue that rap is actually poetry. Dylan’s lyrics are widely considered poetic genius, and Blow is like a godfather of hip-hop. But does this strange duet exemplify this theory? Well, if you’re looking for a laugh, then it does. And who doesn’t want to hear Bob Dylan spit out some mad rhymes? (Dylan is at the beginning and the 6:12 mark.)
The video:

4.
The Collaboration: Jack White and Alicia Keys
The Song: “Another Way to Die”
The Problem: Jack White’s “Black Math” is about as far away—but equally as great—as Alicia Keys “Empire State of Mind.” As strange as their musical collaboration is, they do share an affinity for the blues, so you would think that this colossal collaboration would be like that left hook we never saw coming. Instead, we got something uninspired, bland and just plain boring.
The Video:

5.
The Collaboration: David Bowie and Mick Jagger
The Song: “Dancing in the Streets”
The Problem: Not a bad idea for mash-up of artists. Two classic titans getting down for an old-fashioned good time. Then again, it’s also not a bad idea for an episode of Sesame Street. Bowie and Jagger parade and skip around like Wizard of Oz’s Dorothy and company. Is this a good thing or a bad thing? Regardless, the video is well worth watching for their excellent dance moves. Swag.
The video:

6.
The Collaboration: The Jonas Brothers and Common
The Song: “Don’t Charge Me For the Crime”
The Problem: The Jonas Brothers were probably looking for some edge in their pretty-boy persona on their Lines, Vines and Trying Times album. So what did they do? Hire legit rapper Common to not only drop a few lines, but contribute in a full-on collaborative song. The lyrics are all about the three brothers and Common robbing banks. Picture it . . . . Now hold that image in your head for as long as you possibly can.
The Video:

7.
The Collaboration: Xasthur and Marissa Nadler
The Song: “Horizon of Plastic Caskets”
The Problem: Xasthur was a solo black metal project based in California by Scott Conner, who goes by the ominous title “Malefic.” His version of black metal was much different and alternative from traditional forms, as he didn’t concentrate at all on religion (or a lack thereof). Still, it was a dark, depressing and mournful affair. So when Conner released his final album as Xasthur in 2010, “Portal of Shadows,” who more appropriate to collaborate with than dream-pop-folk singer-songwriter Marissa Nadler? I suppose both artists have an abstract sense of art when it comes to music and Nadler’s voice is deep and foreboding, but when Nadler’s musical act is often associated with words like “pop” and “dreamy,” you’ve got to think: on paper it looks like if Mayhem had teamed up Passion Pit for a dance-pop album.
The Video:

8.
The Collaboration: Game; Tyler, the Creator; and Lil Wayne
The Song: “Martians vs. Goblins”
The Problem: Tyler, the Creator—ring leader of the Odd Future group—teams up with Game on Game’s The R.E.D. Album, and they have Wayne drop in for a little face time, too. And while Tyler’s voice still stands out among other rappers like Wayne’s as distinct and unique, it’s strange that he did this, considering Odd Future’s seemingly strict policy of only working within their own network. It’s not a terrible song; it’s just a little lackluster. You can almost guarantee that Lil Wayne sent his short clip via USPS. Really groundbreaking work here . . . .
The Video:

9.
The Collaboration: Bad Books
The Album: Bad Books
The Problem: Manchester Orchestra, Manchester Orchestra’s leading rotund man Andy Hull and the lesser-known Kevin Devine seem to have their own circle in the indie-rock scene. They haven’t won over many people on the “high-brow” side, since their form of rock still carries a lot of pop influences, but their fan base is sizeable—and vehemently pro anything-having-to-do-with-Andy-Hull. Still, Bad Books feels like Manchester Orchestra’s and Kevin Devine and the Goddamn Band’s throwaway tracks. “You Wouldn’t Have to Ask” clocks in under two minutes, and sounds like an old Weezer song, only not nearly as fun or memorable.
The Video:

10.
The Collaboration: Weezer and Lil Wayne
The Song: “Can’t Stop Partying”
The Problem: Weezer once brought us songs like “Undone (The Sweater Song)” and entire albums like Pinkerton. Now they bring us club anthems like “Can’t Stop Partying,” featuring southern-flavored rapper Lil Wayne. It’s certainly an unlikely and strange collaboration, but it just adds fuel to the fire of the question burning inside every original Weezer fan: “What the hell is Rivers Cuomo thinking?” Although you can’t deny yourself to crack a little smirk when Cuomo sings, “They’re bringing bottles of the Goose, and all the girls in the corner getting’ loose!” Got to give him credit for breaking stereotypes, I guess.
The Video: