Q&A: “White People Rapping Poorly” Mastermind Connor Toole On What Makes Terrible White Rappers So Amusing


Today, the Internet is filled with more depravity and embarrassing footage than anyone could have ever thought possible. Fortunately for us, people like Connor Toole are seeking out the best of the best (or worst of the worst), and posting these .gifs or YouTubes for all to see. His particular specialty, as his Tumblr puts it, is White People Rapping Poorly, and over the past month he’s uploaded 12 pages of the most obscene, cringe-worthy stuff he could find. We talked to Connor about his favorite videos, his thoughts on hip-hop, and his own nascent rap career.

Starting with the basics, who are you, where are you from, and what brought about White People Rapping Poorly?
My name’s Connor Toole. I’m originally from Connecticut. I go to school in Boston.

And what gave you the idea for the Tumblr?
Basically, I was at home over winter break, and I just got really, really bored as it went on, and I spent a lot of time online just wasting time. And I noticed that there was a pattern, that there were a lot of videos of white people trying to rap and just failing miserably. And it entertained me, and I thought, “Maybe it could entertain other people, too.” So I noticed there there were a lot of single-serving Tumblrs that were popping up and getting popular, so I figured I’d hop on that bandwagon. And I made it basically just to amuse myself for a little while, and it just sort of took off.

Do you have a favorite video that you’ve posted?
That’s a tough one. There’s so many on there that I just watched and couldn’t believe. I would say my favorite is probably the series of videos for Tufts University that people made. It was an optional essay for Tufts: Make a one-minute video. And a bunch of kids interpreted that as “make a video of myself poorly freestyling to a beat.” And it was really the night I found those that I realized, “This is going to work out,” because people just have no shame at all.

Do you go to Tufts?
No. I’m actually at Boston College.

Now, is there a genre of these videos that you find particularly funny?
The one that I’ve fallen in love with recently is white teenage girls getting together and making videos. And I just know that the thought process going on in their heads when they’re making them is, “Oh my god, we’re so cute, this is so funny.” And then they put it online, and I watch it, and I try to figure out what possessed them to put it up there for people to see. So white teenage girls rapping poorly is probably my spinoff site, if I’m going to do that

In terms of “likes” or reblogs, do you know what your most popular video is?
There’s a couple that have gotten pretty big…There’s one I posted the other day that’s a German or Austrian guy, and he’s trying to cover “Pretty Boy Swag” by Soulja Boy, and it’s just disgusting to listen to. And there’s another one that’s not safe to print. It’s called “Come Fuck a Guy,” I think, and it’s this guy called Chuggo, and he’s a Dirty South rapper. And the video itself is just a sight to behold, and his rapping to go along with it is amazing.

So are you a fan of rap in general?
Yeah, I’m a big fan, and that’s why it kind of hurts to see people just butcher it like that. I like to think I can appreciate good music, and just to see some of these people just go on and have such a skewed sense of what good music is, and at the same time thinking they should share their awfulness with the rest of the world.

And who are your favorite rappers? Or, I guess, which rappers do you think rap the least poorly?
I’m a big Jay Electronica fan. Big into Mos Def, Talib Kweli. Big Black Star fan. Curren$y, Blu, Lupe. That’s probably my top list of guys.

What about white rappers?
I like Sage Francis out of Providence a lot. And this is a little controversial, but I’m a big Asher Roth fan. Not “I Love College,” but a lot of other stuff he’s done. I really like what he’s doing as a white kid trying to rap. I like Eminem, and I like what he did to basically revolutionize white rapping, so I appreciate him, but I’m not a huge fan.

In what spirit would you say you’re posting these videos? Like, laughing with or laughing at?
It’s definitely laughing at. There’s no doubt about it. I don’t mean to be malicious about anything. My approach is if people are willing to film this knowing what they’re doing, and they’re conscious of what they’re doing, and they’re putting it online to share with the rest of the world, then I think they’re fair game for criticism. And I know some people on different sites have been critical of the approach to what I do, but I think that comes with the territory. And if you’re going to be offended, I don’t think you’re going to appreciate the brand of humor anyway. But it’s not trying to be mean-spirited. I just look at these videos, and I laugh. I can’t tell you why I laugh, I just do. And that’s the reaction a lot of other people have too.

Well, I’m kind of interested then in why you choose to post videos only of white people rapping poorly. Surely people from all different ethnicities rap poorly as well.
For me, it goes back to the long tradition of white people trying to take things that aren’t theirs, not to get overly critical about it. And like I said, I’m a big hip-hop fan, and I look back at the origin of hip-hop and who revolutionized the industry, and I see examples of white people trying to latch onto it and make it theirs and try to embrace what culture has defined as cool. The concept, again, is just something I find funny, not for a particularly defined reason that I can articulate to a T. But at the same time, I think most reasonable people can understand the thought process behind what makes it funny.

Two more questions. First, do you rap?
I do.

I guess that’s part of my motivation too. I don’t consider myself anything too special, but then I listen to what some other people are doing, and I kind of ask if they’re serious and why they’re wasting their time when there are actually people who do care.

And finally, what’s your expert opinion on Tom Hanks’ son’s version of “Black and Yellow”?
Chet Hanks. I mean, there’s the big plagiarism argument going on suggesting that he ripped the hook off, which think is true. But Chet wasn’t terrible compared to a lot of stuff I was listening to. Lyrically, he could probably use a little work, but if Chet has the resources to do what he needs to do, then I say, “Chet, chase your dream.”

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