I'm a big fan of acoustic guitar music. (Bear with me: this is relevant, and some explanation is required.) The two guitar players who got me started were Don Ross at a free concert at the Montreal Jazz Festival around 1990, and a year or two later a battered cassette tape from Toronto Public Library of one of Paco de Lucía's earlier albums (when he was doing straight-up Flamenco rather than Jazz). And of course Leo Kottke. More recently it's been Ewan Dobson and Jeff Fahey. The point is, I'm a fan.
In the last couple years, a good friend introduced me to Django Reinhardt (along with a great deal of other music). I'd heard the name previously, but knew nothing about him. He died in 1953: there are quite a few recordings of him (not so many as there once were), but it's all mono and the quality isn't that great. Despite that, it's still easy to tell that the man was one of the greatest guitar players who ever lived - he's amazing.
The same friend who introduced me to Reinhardt has kept up an email correspondence with me about music that's running on about a year now. A couple days ago I sent that friend an email with the subject line My new online name, and the only thing in the body was "DJ Ango Reinhardt." He responded that he was really glad he wasn't drinking at the time or his keyboard would have suffered.
Here's the problem with this joke - aside from the obvious one that I had to explain it to you in advance, which makes it a lot less funny (which is still better than explaining after-the-fact). The problem is best illustrated by a mental Venn Diagram. The people who recognize the name "Django Reinhardt" are commonly 70 years old and up. The people who are aware that "DJ" isn't just someone who plays records, but also a title and/or affectation of rappers and hip hop artists ... well, that group is commonly 60 and under. You're seeing that mental Venn diagram, with the two circles? Two circles that don't intersect? But there's another possible audience: hardcore music fans (regardless of age, but this requires wide-ranging tastes). This is a group that's likely to know both things.
That first, non-overlapping Venn diagram caused me to characterize the joke as "good but useless" to another friend. But after I thought about it a while longer, I realized that obviously the joke has an audience, because it made a good friend laugh. And what higher calling does a joke have than to make your friends laugh?
The other friend said "nearly spat on his keyboard? Ewwwww." To which I replied "Any story teller or comedian will tell you that causing a spit-take is high praise." You've caused a visceral reaction, a reaction so strong that they couldn't control it. Not only that, but spit-takes are of course their own form of comedy (for better or worse), even if it's only happening in my head because I'm reading my friend's email rather than seeing it.
Another much more obvious "Django" name to mess with would have been "Unchained DJ Ango" ... but I'm not a fan of Quentin Tarantino and his graphic righteous kills.
What it comes down to is "know your audience." If you're standing in your office (imagine the pandemic ended ... there's a glowing mental image) contemplating telling a joke about Donald Trump, you're probably making that Venn diagram in your head without even knowing it. You run through the calculations: "Canadians who know who Donald Trump is ..." Okay, you probably don't bother with that one: that's 100% overlap. Then you think "People in this office who hate Donald Trump and thus will enjoy a joke at his expense." In Canada, that's still probably better than 90% of your audience.