12. Jack White and Insane Clown Posse – Leck Mich Im Arsch
Jack White and his Third Man Records are known for encouraging some pretty out-there concepts when it comes to music, but endorsing the Juggalo movement? Well, I never. Leck Mich Im Arsch saw the poorly matched trio attack Beethoven and is most likely the only Jack White video on YouTube with more dislikes than likes. Go figure. Woop Woop.
11. David Bowie and Bing Crosby – The Little Drummer Boy / Peace On Earth
This particular collaboration shows that just because something looks good on paper doesn’t mean it will work out well. Iconic American singer and actor Bing Crosby with Ziggy Stardust dressed as a normal person in front of an open fire singing time-tested Christmas carols and delivering a universal plea for a better world over the top of each other is cheesiness and awkwardness all wrapped up in a blue cardie.
10. DMX and Marilyn Manson – The Omen
We all did embarrassing things in 1998. DMZ and Marilyn Manson are no different. The Omen found its way onto DMX’s album of that year Flesh of My Flesh, Blood of My Blood and although it’s found on the highly skippable latter half of that album, it doesn’t change the fact they actually thought this will work. Too much evil can be a bad thing – who knew?
9. LL Cool J and Brad Paisley – Accidental Racist
Someone had to end racism, and why the hell can’t it be LL Cool J and country western singer Brad Paisley? Well, here’s why – because accidental racism isn’t actually a thing! It’s actual, real-life racism! And the subtle ways that racism plagues our society won’t be helped by a cute anecdote about wearing a Lynard Skynyrd T-shirt at Starbucks.
