The 10 Most Awkward Rap Music Collaborations

Ever since the 90’s era when Puff Daddy and his Bad Boy crew took rap fully mainstream with their shiny suits and radio friendly songs, hip-hop artists have gotten quite creative with regards to their genre bending experiments. Sometimes these collaborations happen and end up being huge hits like when Jay-Z worked with Linkin Park to much aplomb. A more recent example is Katy Perry recently working with Juicy J for the smash song, "Dark Horse". Those are a few of the good examples. There have been other collaborations that went in the total opposite direction. Some of those songs include the cringe-worthy collab between LL Cool J and country singer Brad Paisley and the sonic disaster that happened when DMX and Marilyn Manson hooked up in 1998. Check the list out below – we just have to warn you that some of these collaborations are even weirder than you could ever imagine.

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10 DMX/Marilyn Manson


In 1998, the Def Jam records rapper DMX was having a great run in the music game. He was dropping #1 albums, releasing Billboard topping singles and selling out concerts everywhere. He even had the confidence to stray way out of his hip-hop comfort zone and record a song with the goth-rock singer Marilyn Manson. The song was called “The Omen” and it featured Manson on the song’s chorus. In all honesty, it was one of the worst songs on the album. On paper it might have sounded like a great idea, but at that point both artists were really big names in music, and they should have been able to come up with a much better product.

9  9. Limp Bizkit & Method Man


In the late 90’s, the rap/rock music mix was really a big thing. Groups like Linkin Park and Limp Bizkit were selling out stadiums and selling a ton of records too. One of the most memorable songs of that era was the “hardcore” hip-hop duet between Fred Durst (frontman of Limp Bizkit) and Method Man of The Wu-Tang clan. The track was produced by the legendary DJ Premier of Gangstarr and it received some decent play on MTV. In retrospect, the song wasn’t such a good idea; a group with as much street cred as Wu-Tang shouldn’t have worked with a band that was more or less a passing fad.

8  8. Kanye West and Paul McCartney


7 LFO feat M.O.P.


Hailing from the tough streets of Brownsville, Brooklyn, the hardcore duo known as the Mashed Out Posse or M.O.P. has the reputation of being one of the hardest groups in rap music. But they made a musical move in 2001 that had a lot of people scratching their heads. They decided to do a group song with a group called Lyte Funky Ones (LFO) for the Dr. Doolittle 2 soundtrack. The song was called “Life Is Good” and it totally went against the M.O.P. brand and everything they represented. They may have a gotten a decent check for appearing on the track, but sometimes keeping your integrity is much better than a quick payday.

6  6. Justin Bieber feat Raekwon


Some collaborations should never happen in music, and the song “Runaway Love” in 2010 by Justin Bieber featuring Raekwon of the Wu-Tang Clan is one of them. This questionable track was apparently concocted by Kanye West and it ended up being an amalgam of Bieber’s pop sound and a hardcore street track from the Wu-Tang’s debut album. Perhaps Raekwon saw the track as an opportunity to reach out to younger music fans, but honestly, some lines of musical integrity should never be crossed.

5  5. LL Cool J and Brad Paisley


As a rule of thumb, when someone comes up with an idea to do a song titled “Accidental Racist,” it might be a good idea to walk in the opposite direction. Well, that song actually got made, and it was a collaboration between country singer Brad Paisley and rapper LL Cool J. In the song, both of them tried to explain how their innate culture and behavioral tendencies don’t necessarily make them racist. On the song, Paisley sang, “Cause I’m a white man livin’ in the Southland/ Just like you I’m more than what you see.” LL Cool J also delivered lyrics like, “Just because my pants are saggin’ doesn’t mean I’m up to no good/ You should try to get to know me, I really wish you would.” Perhaps they had good intentions but the execution was quite poor.

4  4. Nelly and Tim McGraw


This is one song that proves that there is always an exception to the rule. Even though this collaboration between the rapper Nelly and country singer Tim McGraw was extremely unexpected, it ended up being a huge hit. The song was featured on his 2004 album called Suit, and it was titled “Over and Over.” The song reached number 3 on the Billboard charts and it also managed to top the charts in Australia, Ireland, New Zealand and the United Kingdom. It also did really well in Austria, Canada and Denmark. Hey, maybe Nelly just has that magic touch.

3  3. Weezer and Lil Wayne


The rock group Weezer is one of those amorphous bands that always like to stay current with the times. However there are actually situations where it’s prudent to stick to your guns and not try to follow the current trends making waves on radio. For their 7th studio album called Raditude, Rivers Cuomo, the band’s leader, recruited Jermaine Dupri and producer Polow Da Don for a crossover track called “Can’t Stop Partying.” He also invited Lil’ Wayne to rap over the song. He might have thought it was a good idea, but longtime Weezer fans weren’t fond of this unwarranted experimentation.

2  2. Jonas Brothers and Common


Wow, how times have changed. It’s 2015 now and Common recently won a Golden Globe award for his musical contribution to the movie Selma and Nick Jonas is enjoying a great musical moment with his song “Jealous” going #1. But in 2009, it was a totally different story.  The Jonas brothers were prepping to release their album Lies, Vines and Trying Times and they recruited Common to appear on the track titled “Don’t Charge Me For The Crime". The song itself wasn’t that horrible, but as far as Common’s music collaborations go, it’s not even close to the usually high standards he usually keeps.

1 Bone Thugs N’ Harmony and Phil Collins


In 2002, the group Bone Thugs and Harmony were going on their fifth album and their popularity was starting to decline. In one of their brainstorm sessions, one of their group members probably came up with the awkward idea of doing a song with soft rock legend Phil Collins to get them back on track again.  The name of the track was “Home” and it features a Phil Collins sample from his 1985 hit, “Take Me Home.” Even weirder, the Ohio rap crew had to travel to Geneva to film the video because that’s where Collins and his family were celebrating the holidays. You really couldn’t make this stuff up if you wanted to.

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