Over the last few decades, all sorts of television shows have tried to capture the essence of rap. While there are certainly some fantastic examples over the years that encapsulate everything we want in a fictional rapper (most recently Paper Boi in FXX‘s Atlanta), we’ve also seen a fair amount of misses that make us wonder what sort of conversations were had behind the scenes. Our best guess is that every so often a TV executive, having just heard hip hop for the first time, would burst into a writer’s room, slam their niece’s Now That’s What I Call Rap album on a table and say, “THIS! We need to do this!” without thinking of how that would work on the show.

It’s those very instances, and some other purposely comedic ones, that we see as a necessary step in the evolution of getting things right in TV’s rap game. They may not always be perfect, but every attempt is a step in the right direction simply because creators continue to try. We’ve compiled our favorite examples of the funnier side of fictional rap, including some that can actually be considered pioneers for introducing a musical art form to an audience that may not have heard it otherwise. The road is paved with the trial and error of well-meaning TV shows and tongue-in-cheek homages to the art form that have had an impact on us. Here are some of our favorite fictional rappers from television.

Bartman

For a certain slice of fandom, this hits a special chord on the heartstrings. “Do the Bartman” was part of the (in retrospect) absolutely baffling trend to infuse the coolness of rap into everything imaginable. This song, which was co-written by none other than Michael Jackson, was absolutely everywhere for a time. It climbed a fair amount of music charts all over the world as if Bart was a real artist, and the trend continued with other Bart-sung songs like “Deep Deep Trouble.” This trend of Rap-itizing (that’s probably a word TV execs really used) TV shows like The Simpsons didn’t stop at animation.

Urkel

At some point, every sitcom in the ’80s and ’90s seemed compelled to try and capture lightning in a bottle in the lamest way possible. Family Matters was no exception by combining its most popular character with the words “Do”, “The”, and “Dance.” It didn’t work to the level Bartman did, but chances are you could play a few moments of this song for most 30-somethings and they’d be able to tell you what it was. Urkel and his eponymous dance may have been the most successful of the rap attempts in live-action shows if not for…

Baby Sinclair

To be fair, this Dinosaurs-inspired song only has a rap-like breakdown but we’re still counting it. You may think that we here at Nerdist.com are favoring the Jim Henson creation over other fictional rappers and, well, you’d be absolutely right. But think about it: out of all the songs on this list, you’ve probably already shared this to your Facebook page and will at least have it milling around in your head for the next few days.

MC Pee Pants

MC Pee Pants (and later, Sir Loin) was the occasional scourge of the Aqua Teen Hunger Force (or whatever they might be called these days) who was constantly trying to pull some rap-related scheme whether it was for candy or “4 da shorteez.” He was voiced by real-world rapper MC Chris, whose own music is similarly pitched, decidedly nerdier, and substantially less scheme-related. Chris has put out quite a few albums full of nerdy references woven into the bars and book-ended by incredibly catchy hooks.

And while we’re on the topic of Adult Swim shows…

Brak

Are we the only ones to remember The Brak Show? An Adult Swim OG show that was a nonsensical spin-off sitcom (we guess?) of Space Ghost Coast To Coast, it featured classic tropes like school music contests including this rap battle that, thankfully, still lives on inside YouTube. Some eagle-eared (that’s not a term) listeners may recognize the voice of the superior rap monster named Prime Cut Miggity-Mo’ Macdaddy Gizzabang Doggy Dog Dog as the one and only Cee Lo Green. [Side note: Life’s real weird when you have to type sentences like that.] Anyways, let’s get back on topic to someone serious about changing the rap game.

MC Skat Kat

Ha! Just kidding. This was bananas. How odd that we can all collectively love a rapping animated cat in the “Opposites Attract” video but give him his own song and it turns into the lamest thing in the world. Well, maybe not as lame as the furry MC Skat Kat Paula Abdul performed with on stage.

Kidding aside, we’ve saved the best for last. Nothing says hardcore rap skills like two folk singers from New Zealand.

Hiphopopotamus vs. Rhymenoceros

We called an audible here and shared the live version from the Flight of the Conchords HBO special instead of the one produced for their series. In part because we think this acoustic version works much better to deliver the overall joke of the song while the music video they produced for television comes off just a little too cool. Seeing Bret McKenzie and Jemaine Clement switch between over-confident “gangster” personas to showing perfectly comedic vulnerability is what makes this one of our favorite quasi-fictional rap duos ever. We say quasi-fictional because we have our fingers crossed that these are really the default personas of McKenzie and Clement and everything else is just an act.

Let’s see, we know our audience and how leaving out some could cause a comment storm. So let’s give some honorable mentions (left out of embedding for obvious inappropriate reasons) to Gangstalicious from The Boondocks, Taquil on Frisky Dingo (Google that on your own, folks. You’ll understand why), and Alpa Chino from 2008’s Tropic Thunder.

There are, of course, many other examples of fictional rappers so we want to hear your favorites. Share them in the comments below!

Image: Fox