I'm not a Juggalo but my brother is, so I know a lot about that community that the average outsider probably doesn't.
But also I'm an Otaku. Being an Otaku and a Juggalo are kind of parallel in how to outsiders it just seems like a fancy way of saying you're a fan of something (Anime in one case and in the other the Insane Clown Posse hence forth called ICP for short and affiliated artists), but there is in fact a deeper hard to define identity behind it. You weren't an ICP fan before you listened to ICP music but you were probably already a Juggalo. Likewise I only got enough into Anime to even start considering calling myself an Otaku in the latter half of 2016, but what an Otaku is I in fact always was.
There is also how it sometimes becomes almost a quasi religion. While Juggalos symbolize God as a Dark Carnival of freaky clowns, Otaku symbolize God as a Cute Anime Girl in Sailor Fuku.
Also like with a lot of insular fan communities that chiefly interact online there has been post Gamer Gate an increasing visibility of the loud minority of political reactionaries in each community tainting how they were once perceived as fairly inherently progressive. My brother and I are both Socialists.
One of the roles I have self appointed myself in the modern Anime community is being someone who thinks they know how to recommend potential entry points to people who haven't tried it yet. And in this case one of the things I think Juggalos and Otaku sometimes have in common is their sense of humor.
You see I think I might very well be the only non Juggalo who's watched Big Money Hustlas and found it funny, I get the sense of humor it's going for, meanwhile Big Money Rustlas which has had better luck at getting nice things said about it from Normie critics I found rather unappealing.
Now there are a lot of Comedy Anime out there going for a lot of different styles of humor. But the first Anime to pop into my mind as material that might be enjoyable to the same people who find Big Money Hustlas funny are Nabeshin shows like Nerima Daikon Brother and Excel Saga. The first one I listed is probably better for people new to Anime, if you've seen The Blues Brothers you have basically have all the pop cultural context you really need. Excel Saga has a lot of meta going for it that makes a working knowledge of the 30 years of Anime history leading up to it helpful, but still I don't necessarily think entirely necessary. I hate that neither show it seems can be legally streamed online right now.
Those are comedy recommendations. Juggalos are also known for being into the Horror genre. Recommending Horror Anime has already become a recurring theme of this blog, but it's become increasingly necessary for me to qualify my recommendation of Higurashi When They Cry.
Please for the love of God start with the 2006 Deen Anime and then it's sequel Kai, and then take a break, contemplate that story knowing that for a long time what was all there was, they are legally streaming on HIDIVE and can be found for free on sites I won't risk linking to here. Then maybe give the Rei and Kira OVAs a shot but their canonicity was always ambiguous at best and their goofiest episodes definitely not cannon. For the Gou series that started in late 2020 and it's follow up Sotsu which is still airing (officially in English often called Higurahsi When They Cry New) I won't have a final verdict till I see how it ends which I now fear even Sotsu won't have the final ending, right now my feelings are complicated leaning towards not liking it.
Now when it comes to Umineko When They Cry, as the only person who seems to truly love it's Anime version, I think Juggalos if they found it might appreciate it. It can't legally be streamed anywhere right now however.
For Zombie Media, the Anime equivalent to the George A Romero films would be School-Live! aka Gakkou Gurashi! While something more like Zack Snyder's Dawn of The Dead for better and for worse would be High School of The Dead. Both are also on HIDIVE along with Vampire Hunter D and Princess Resurrection which I haven't watched yet.
The 80s Vampire Princess Miyu OVAs are on TUBi, RetroCrush and Midnight Pulp if I remember correctly.
Many Juggalos are also into the Music of Bone Thugs N Harmony, and I have two kinds of recommendations based on that. First my favorite Anime Composer, Yuji Kajiura, has a musical style that I feel can at times have a similar appeal to that of DJ U-Neek who is Bone's main Producer.
She did the music for most of the old Bee Train shows of which I still consider her best work to be Noir followed closely by it's sister serises Madlax and El Cazador de la Bruja. She then did Mai Hime a show I still haven't watched most of yet, and the Kara no Kyoukai films, then really hit it big in 2011 with the one two punch of scoring Fate/Zero and Puella Magi Madoka Magica. Since then she's done Princess Principal which was great, Demon Slayer which is a Shonen I didn't watch, the Heaven's Feel Trilogy, Lord El Melloi's Case Files and more.
She also did the Music for at least one Live Action Japanese film and that's the Boogiepop movie from 2000.
Boogiepop and Others is a series of Light Novels that started in the 90s that in-spite of their influence didn't get a proper Anime till 2019. The Author of that series liked to reference in various ways the Music he was into. And one of those was clearly Bone Thugs N Harmony because the prequel novel features a character named Mo Murda (but that gets back translated into English Localizations as Mo Murder by people not getting the reference) which is a confirmed reference to the multitude of songs Bone made with some variation of that title.
The 2019 Boogie Pop Anime is difficult to talk about, because I found it pretty enjoyable when I watched it not knowing what they cut. But it's first three episodes are to anyone in the know a frustratingly abridged version of the first novel. The live action movie is a much better adaptation of that source material.
The 2019 Anime still has value, the books adapted for the latter half of the 18 episode season I feel were adapted much better, at least in that the Anime version can stand on it's own better. Episodes 10-13 is the Prequel story, Boogiepop At Dawn which contains the Bone reference character mentioned above.
The Live Action Boogiepop movie doesn't and shouldn't have a Dub, for LA that's an inherently more awkward process. For the 2019 Anime I like the English Dub but I'm known for being not too Dub critical in general, either way of consuming it should work fine, do what ever you'd generally prefer. Same is true of everything else recommended except Higurahsi Kai and Umineko which sadly don't have Dubs. Nerima Daikon Brothers might be the one that's most better to watch Dubbed, since it's unique musical nature can be harder to follow subbed even for people very used to it, that of course could make it more difficult for a Dub to work, but they pulled it off spectacularly.