Hello, it's me, the guy who's constantly banging on about tabletop roleplaying games on a website that's supposed to be about PCs. If you thought Black Friday was going to stop me, you were sorely mistaken: I've been digging up D&D and other TTRPG deals like some sort of polyhedral dice-obsessed badger, and I've got the very best ready for your waiting eyes.
With the big «OneD&D» rules update on the horizon sometime next year, it's a weird moment for D&D 5e deals. On the one hand, a lot of books are selling at really significant discounts; on the other, it's because they're probably going to be made obsolete in the next 12 months. My recommendation? Use the opportunity to pick up some good adventures, which should remain compatible with the new rules, but avoid corebooks and supplements unless you're at peace with having some outdated material in your library.
Or, ignore D&D completely, and use this as an opportunity to check out one of the many other fantastic TTRPGs going super cheap this year.
If you're totally new to D&D and not sure where to start, the Essentials Kit is the best buy right now by my reckoning. It's only slightly more expensive than the Starter Set, but contains more stuff that should keep you going for longer. Don't pick up the core books unless you really want them, as they'll be going out of date next year—the Starter Set and Essentials Kit both contain everything you need to play, and you can reference most of the core rules for free on D&D Beyond anyway.
Dungeons & Dragons Starter Set
$19.99$13.99 at Amazon (save $6)
With ready-made characters, a 48 page adventure, rules for levels 1-3, and a set of dice, this new starter set will get you right into Dungeons & Dragons with a minimum of prep