I'm a big fan of a bloke called Sorcerer Dave, mostly because he does Oblivion, Morrowind and Skyrim content (With some Fallout NV here and there). I've watched a little bit of CouchWarrior recently, and I have to say I enjoy his presentation and roleplay focus, but I'm not quite into it enough to decide one way or another.
Oh and PCOutcast is of course on my list, great content and an awesome guy in general.
He doesn't make Skyrim videos anymore (at least I don't think he does), but Gopher is still one of my favourite 'Lets Play' Youtubers. Sexy voice + Dry wit = Awesome.
Brodual might not be necesarily creative, but the way they show off mods really appeals to me, and eventhough I can't get most of them, thinking about how fun and different the game would be with those mods is quite fun.
There's also a bloke called Barbell Gaming, who's quite small but I really enjoy his Lets Plays as well, although he isn't very consistent anymore his goofy comedy brings life to an old game.
Does anybody know this channel : https://www.youtube.com/channel/UC-i3WnEFcTntkZc-Pv9gArw ? I personaly found this videos very funny (not only skyrim though).
And to answer the question, I first watch Gopher's videos in which he does mod presentations and then I started to go through RP playthrough of the game with Rycon and his serie featuring Leonidas, also Gamerpoets with the tale of Paxton.
Right now I watch CouchWarrior, and I try to catch up with the unbelievable amount of videos he had done.
I love General Sam, Couchwarrior, Gopher, numidium3, and Brodual. Not sure if the Elderscrolls Lorecast on memospore counts, but they're probably my favorite. I used to be really into Fudgemuppet, but sadly I feel that they've sacrificed video quality for jumping on the Skyrim SE hype train and just throwing shit at a wall and seeing what sticks. Though I really hope they boost their quality again soon, I miss their good videos.
I cannot believe no one has mentioned GROHLVANA. He is a fantastic youtuber. He does only bethesda games and has extensive let's plays for "Fallout 3", "Fallout New Vegas". "Fallout 4", "Morrowind", "Oblivion", and "Skyrim". He has excellent commentary and a really good community. He also does a lot on Twitch. He is super good and is way underrated. It would be awesome if you guys would go to his channel and check him out.