Fifth Edition DnD is the latest edition, starting less than a decade ago and currently still releasing. The Fifth Edition served to simplify a lot of the elements of 3rd and 4th Editions and make them extremely user friendly to new players. This was incredibly useful, helping to draw in new users as the game got a revival in the mid to late 2010s. This was largely due to the growing DnD community online, who used social media such as Facebook, YouTube, and Discord to become a lot tighter knit and able to converse than in previous generations of the game.
It wasn't too long before what may be the best part of Fifth Edition came around, an extremely user friendly DnD character builder known as DnD Beyond. While there was and still is some controversy surrounding the product, since those who have bought the physical editions of books have to buy them again to have them function in DnD Beyond, the extremely easy to use product gained traction and made a lot of people find getting into the game a lot easier than before.
Critical Role is a Podcast series that is a quick recording of long running DnD players playing their game. The game is very tight, and all the players are professional voice actors which lends a lot to the gameplay. This helped to spawn a whole genre of live play DnD podcasts, most of which can be traced back to Critical Role.
One of the other most famous Podcasts, which is even sillier than Critical Role, is the Adventure Zone. The Adventure Zone is a podcast run by the McElroy brothers who are well known now as being creatives who run several podcasts. The final member of the group is their father, Comic Book writer, Professor, and former Radio Personality Clint McElroy. The Podcast follows a lot of similar beats to their other podcasts, and uses the pre-determined audience to get started.
Another popular podcast is DnD is for Nerds by Sanspants radio, a podcast group in Australia. This group's campaigns are a lot shorter, which makes it a lot easier to get into for new listeners.
A few years back a change in the YouTube algorithm allowed for animation content to return to the platform. After a long hiatus, due to the algorithm giving preference to longer, low-effort, quick to produce videos over short animations, a new genre was born called animated Storytime videos. These short, pithy, videos tend to be about 15 minutes with very limited animation set to the creator telling their own stories.
It wasn't long before this style was adopted to DnD, the most famous of which is Puffin Forrest. Puffin Forrest created a video series just based on DnD stories of his life, and slowly gained a following.
Soon others would join, the largest contenders being Jocat with his Crap Guide to DnD series, Dingo Doodles who leveraged her web-comic audience into a small boost that shot her first video on her channel immediately to the home screen that quickly became a YouTube sensation, and Zee Bashew with his animated Spellbook series.