By clicking “Accept All Cookies,” you agree to the storing of first- and third-party cookies on your device to enhance site navigation, analyze site usage, and assist in our marketing efforts

The 10 Most Embarrassing Rap Battle Fails of All Time

Once upon a time, Canibus was one of the most feared battle rappers in the rap game. Thanks to his guest appearances on songs like the Lost Boyz’s “Beasts From The East,” Common’s “Making a Name for Ourselves,” and The Firm’s “Desparados” as well as his solo tracks like “Second Round KO,” ‘Bis was viewed as a beast on the microphone in the late 1990s. But, oh, how the mighty have fallen!

Over the weekend, Wyclef’s former protege was involved in a pay-per-view rap battle against fellow battle rapper Dizaster organized by King of the Dot, a Canadian hip-hop battling league. And, after stumbling out of the gates and falling behind in the battle, Canibus resorted to doing something that should never, ever be done during a war of words. He forgot the lines he’d pre-written for the battle, so he took out a notepad and starting rapping off of it. Then, he forfeited when the crowd (understandably!) began booing him relentlessly. And, for whatever reason, he was wearing a sling around his right arm when he did it. It was a sad moment for those of us who remember how great Canibus was back at the beginning of his career.

Fortunately—for Canibus, at least—this isn’t the worst rap battle fail we’ve ever seen. In fact, over the years we’ve seen way worse. From MCs getting into physical altercations in the middle of battles to rappers who have accidentally spit wack lines about themselves to one MC who actually peed on himself during a battle, we’ve put together a list of The 10 Worst Rap Battle Fails of All Time. It’s just too bad we have to add Canibus to this list now.—Chris Yuscavage

The Rapper: Nyckz

The Fail: Everybody remembers the Internet meme that this rap battle created. During his verse, Nyckz dropped the memorable line, “Oh, you mad ’cause I’m styling’ on you?” and it instantly took off. What you probably don’t remember, though, is that Nyckz’s opponent E-N-J responded to that line by punching Nyckz in the face to end the battle. That turned this into a fail on both sides.

The Rapper: Rapper unknown

The Fail: We’re not sure who this guy is. Really, it doesn’t matter. All that matters is that he kicked a verse during this rap battle…and then peed his pants. And, the best part? It completely threw his opponent off and he actually won! It’s still a huge fail, though.

The Rapper: Charles Hamilton

The Fail: After taking an L in a rap battle to Serius Jones, CH tracked Serius down at a barbershop in Harlem and attempted to battle him again. But, Serius basically told him, “Go find somebody to put some money up for the battle first,” after Charles attempted to engage him and walked away without agreeing to a battle. And yet, for whatever reason, we still thought Charles had a good thing going with his rap career after seeing this. We failed here, too!

The Rapper: Charles Hamilton

The Fail: You knew the first CH battle fail wasn’t going to be the only CH battle fail on this list, right? In this clip, he battles his girlfriend Briana and she gets so mad at him at one point that she punches him in the face. Truth be told, this might be the worst fail on this entire list.

The Rapper: Unknown rapper

The Fail: We’ve obviously seen punches thrown during and after rap battles before. But, we’ve never seen punches thrown like this. After losing a battle, one amateur rapper gets so mad that he sucker punches the opposing rapper, body slams him to the ground, and then sucker punches him again once the guy gets up and tries to talk smack into the camera. Was it really that serious, dude?

The Rapper: Tah Phrum Duh Bush

The Fail: When you’re battle rapping, your mind has a tendency to wander. But, it should never wander to where this Brooklyn MC’s mind wandered. In a matter of two minutes, he spit a series of different punchlines that worked against him instead of for him. The worst one? “Yeah, my penis is kinda small,” he rapped, “but it’s small enough to get in and dent your p—- walls!” Um, wait…WHAT?!?

The Rapper: Dose

The Fail: Although he sounded plenty tough in his rhymes during a battle against a rapper named Math, Dose took off running at the end of their battle after Math punched him in the face. Lesson learned: If you’re gonna talk smack, you better be able to back it up!

The Rapper: Cloud 9yne

The Fail: A slip of the tongue is the last thing that a rapper wants to have during a rap battle. Yet, that’s exactly what happened here. This guy attempted to put together a punchline that involved the phrase “big d— in my f—— draws.” Instead, it came out “big d— in my f—— jaws.” Oops. Couple that with the fact that he resorted to yelling throughout his entire verse and this was one big fail.

The Rapper: Bones Brigante

The Fail: It’s still completely stupid, but we can understand why rappers get into fights during battles. There’s a lot of pride and ego on the line and sometimes feelings get hurt. But, this particular fight seemed stupider than most. Canadian rapper Young Ruge mentioned a Canadian rapper named Bishop Brigante during a battle against his opponent Bones Brigante. And, for whatever reason, that set Bones over the edge, ignited a riot, and ended the battle. Was it really worth all of this over one half-hearted diss?

The Rapper: Envy

The Fail: Okay, so we wouldn’t necessarily call what Envy did here a “fail.” But, from the looks of things, he was set up to get an easy W here when the producers of this “Iron Mic” freestyle battle matched him up with a kid named Eli Porter, who appears to be mentally challenged. But, he lost. The production value of this video was a big fail, too. Who thought this was a good idea?

Jump to comments