Theophilus London has had an interesting career. Was kinda on that wave with Solange and co. back around 2010 (if you haven't heard "Flying Overseas", go look that up on YT) and then was associated with Kanye and his crew for a while and now he just kind of pops up sporadically with cool stuff like this.
He also did a "cover" of Jolene called Based God so that's a thing in the universe as well.
I can definitely see how someone not plugged in to hip-hop or someone who wasn't in school when his early stuff was popular wouldn't have that connection with him. He had a relatively short period where he was a name that everyone knew for people from probably about 22 to 27 or 28, people outside those age ranges probably wouldn't have that same cultural connection with him and none of his other work really ever caught on big and he never had a radio hit.
2009 is a beautiful song but it really is so sad. The Tiny Desk version is incredible along with the whole set. Mac really just was an amazing dude with an extraordinary passion for music who genuinely seemed to care about people, it is no surprise to see so many people who knew him express such high praise for him.
Let's be honest though, "Wavin' Flag" was the real song of the 2010 World Cup. Maybe not the official song but I bet a lot of people have stronger associations with that to the World Cup than Waka Waka.
If anyone hasn't done so yet, I would highly recommend looking up Michael Dapaah's other comedic work besides his Big Shaq character on Youtube. Genuinely hilarious stuff if you have even a cursory understanding of English culture.
There's a clear and obvious level of respect that can be seen in Wu-Tang and The Boondocks that isn't nearly as apparent as Nicki Minaj playing dress up.
I think what has prevented him from seeing the same kind of large scale criticism that Iggy Azalea got is mostly how he seems to carry himself. He doesn't seem to take himself particularly seriously, especially when it comes to rapping, as if he is fully aware that he isn't very good at it. That is obviously really problematic itself but it certainly differentiates him from Iggy Azalea, who seemed convinced she was truly a great rapper.
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