Wired describes the deep web most succinctly as a "collection of thousands of websites that use anonymity tools like Tor and I2P to hide their IP address." The key is decentralization, meaning that no regular browser (Chrome, Safari) can access these websites. Instead, the user must obfuscate their online identity in order to be granted access.
To many, the deep web is simply a place to buy bizarre and potentially illegal things. Silk Road was the first website to popularize this method. It trumpeted Tor browsing as the best way to avoid online surveillance. It wasn't just a way to buy illegal goods, but it also deanonymized web browsing as a political ethos.
Beyond illicit marketplaces like Silk Road, there's much more to see. For instance, it's the best way for privacy activists to communicate with each other. There are also numerous online boards, wikis, and chats for people trying to divulge information they don't want associated with their identity.
The best kinds of dark web content are the privacy and ideological discussions.