I first heard about Dimension 20 when they were doing their New York-set campaign called The Unsleeping City. Created for College Humor's Dropout streaming service, it's a D&D webseries played by various funny folks out of the now-defunct College Humor comedy site (though it appears Dimension 20 is still around.)
If you've watched Critical Role, Dimension 20 is a somewhat more carefully produced version of D&D "real play." Rather than live-streaming, the show is recorded and edited somewhat (though not scripted) to allow for sound effects and various close-up shots of the really excellent minis they use.
The comparison with Critical Role is tempting to make, as it's a show that benefits from the fact that its cast is composed of professional performers. However, while Critical Role gets into the long-haul, years-long campaigns, Dimension 20 has done several shorter-term campaigns over its two years.
And the premises for these campaigns are, in a word, heightened. While they've had other players come in for some of its 6 seasons, they've had a regular cast for three of those (I believe the other campaigns have been separated out as "side quests.")
Anyway, the two that I've watched a lot of (though I realized that I never finished the latter) are Fantasy High and The Unsleeping City. The former has the following pitch: D&D meets John Hughs teen movies. The latter is a sort of hidden-fantasy-world-within-the-real-world magical-not-so-realism kind of premise.
The point is, both of these series set high-magic fantasy stories in a world with cars, subways, cell phones, and modern concerns and environments.
Ever since I read the Dark Tower series by Stephen King, I've always been kind of obsessed with the idea of taking Tolkienesque fantasy tropes and using them in a modern setting (admittedly, that's really the jumping-off point - like King, I'm very into surreal weirdness.)
The way that Dimension 20 approaches the modern settings in these two campaigns is somewhat different. Fantasy High is set, essentially, in a classic D&D fantasy world, but in which some combination of technological, sociological, and magical progress has created a world that appears quite similar to the latter half of the 20th century and the early 21st. This world is explicitly within the standard D&D cosmos - there are references to Acheron, the Nine Hells, and the distinction between Devils and Demons (though the major devil NPC, who turns out to not be that bad of a guy, actually, is still mostly referred to as a demon for the benefit of people who aren't giant nerdy lore sticklers.) But the player characters are all high school freshmen who have been sent to the Aguefort Adventuring Academy, where the insanely violent life of fantasy adventurers is thrown in up in relief against the reality of teenage life.
Certainly, fantasy stories in high school are nothing new (see: Buffy the Vampire Slayer,) but the series derives a lot of humor from the fact that the sort of person who would run such a school for actual children would have to be a violent psychopath.
The Unsleeping City does something I find really fascinating by taking elements of the real world and interpreting them as if they were the deep lore of a fantasy world. Robert Moses, for example, is a real historical figure who did a lot to shape the way that the city of New York developed, and he plays a key role in the campaign.
I used to live in a neighborhood of Los Angeles called Eagle Rock, and I remember wanting to come up with some sort of fantasy equivalent of the city in which there was some majestic, ancient, intelligent eagle that was a kind of oracle there.
Actually, if you've ever read Neil Gaiman's Neverwhere, I'd say there's a similar vibe to the Unsleeping City.
Anyway, if you find yourself looking for an online D&D show, I definitely think this is worth checking out.
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