Dropout

I think the first season (Fantasy High) is a good start. It's a relatable setting and since it was Aly's first time playing, you learn with them.

Other than that, there is Never Stop Blowing Up. A short silly season where they don't use D&D. It's a good intro to role playing. Although the game system does start to show it's flaws towards the end.

@Ideonek Despite the “where to start” video, if you specifically want to introduce someone to watching D&D for the first time, I think Dungeons & Dragons Queens is a better start than Fantasy High. The gameplay is even more accessible, and it’s nice and short (no 40hr commitment). I’d only recommend FH first if someone is already, like, *super* invested in the John Hughes mashup aesthetic and utterly uninterested in Drag Race vibes.

@Ideonek I don't think there are any true one-shots, but the first season (and it fully stands on its own) of Misfits and Magic is only 4 episodes. It's extremely accessible, though it makes fun of the Harry Potter universe a bit, so knowledge of that is helpful. The players are Dropout regulars Lou, Brennan, and Erika, plus Danielle Radford, and GMed by Aabria.

It uses a pretty rules-light system (Kids on Brooms) in a twist on a famous setting. Easy to get into and ton of fun.