I love the channel for the Chess Club and Scholastic Center of Saint Louis. It has numerous lectures targeted for beginner, intermediate, and expert players that cover a wide range of topics while analyzing games. The lectures are given by various GMs and IMs. Check out Ben Finegold's lectures, He is a great teacher and never fails to crack me up.

https://www.youtube.com/user/STLChessClub

I liked John Bartholomew's "Climbing the Rating Ladder" videos, where he plays players of different levels and talks about strategy and common mistakes at each level:

https://www.youtube.com/watch?v=U2huVf1l4UE&list=PLl9uuRYQ-6...

I love those kind of annotated videos. I had one of the Chessmaster series (9000 I believe) which had videos by Josh Waitzkin where he did the same thing, often going into the psychological side of the game too. I spent a summer addicted to that program and my skill skyrocketed.

I also quite like the banter blitz series from chess24. Svidler and Gustafsson are fun to watch and listen to.

https://www.youtube.com/user/chess24media/playlists

https://www.youtube.com/watch?v=YvxuZooPUPA Svidler's session from earlier this year

Less educative but more entertaining is Grandmaster Eric Hansen's channels called "chessbrah" on Youtube and twitch.