I felt Dracula's Ex-Girlfriend did have its virtues as a script. I know it sounds stupid, but I don't consider that I would have the right to continue criticizing Olly for other things, if I didn't make the effort to expand on this.
I think there is a grain of unselfawareness required for being an artist. (Like Contra not succeeding as a novelist, and instead becoming an analytical philosopher: too self-conscious.) I think Olly has that grain, and he also has a highly active fantasy life, which is a writerly asset. He does show an ability here to "give" a situation with convincing characters, just with the power of his emotional energy.
After my watch I concluded that the script at least went through several rewrites, and I wasn't surprised when, in the behind the scenes video, Olly confirmed this. He said that it was always going to be about Fay recovering from an abusive relationship with Dracula, but his original take was Fay trying to become human by talking to a therapist. Then he decided the therapist character was too boring and invented Belladonna instead—and changed his conception of Fay, too, making that character into someone "trying to be a therapist" to Belladonna.
I was genuinely pleased to hear about all this chopping and changing—because this process of searching for the right form, to best express a particular story, is of course the way real writers work. I think the project being a collaborative effort with Morgana Ignis, which they both talked about in the behind the scenes, is what was responsible for the relative level of polish here—since Olly actually had a reader, he had someone to tell him his first draft sucked, and to inspire him to rethink his conception of the narrative. (He framed it like it was his own fun-loving self who decided the original therapist character was too stuffy, but I doubt he was all that dissatisfied with his original draft—if that godawful death poem in his last video is any indication, he's incapable of self-criticism in a vacuum, and his first instinct is always to go with his first instinct.)
None of this is to say that he has any integrity as a scriptwriter—if he did, he would put way more effort into the little skits in his own videos (and bring to them that same patience and willingness to revise which he showed in his writing process for Dracula's Ex-Girlfriend). And if Dracula's Ex-Girlfriend works on the script level, it fails utterly in execution, for reasons which have been thoroughly outlined by many canny and observant people in this thread.
And in my opinion, a failure of willpower will forever keep Olly from creating worthwhile art.
He said once in an interview:
But it's always, certainly since I really started letting my creative flag fly on the show, it's always felt like the videos have come down in a beam of light, and I make them. And every time I start with a blank piece of paper and I make a new work of art.
Very pretty words. But the fact is that making art takes some sweat and drudgery (the first draft after the "blank piece of paper" is never art). It also takes self-knowledge about your strengths and weaknesses—knowing what you
can do, in addition to what you want to do—which can mean having to give up on certain dreams. But I think Olly will always prefer what is easy to what has integrity. Although he has no talent for acting, he'll always chase his adolescent fantasy of being a movie star, just because the idea lights up his pleasure centers.
I found Dracula's Ex-Girlfriend actively unbearable to watch when Olly was onscreen. I think because the character was more theatrical, that brought out all the worst in Olly's acting. When he's playing a more drab role, like that bit on Ladhood, your eyes slide over him and you don't notice as much how wooden he is. But when he's enjoying himself, he's so greedy to be praised for all his "subtle acting choices" that it's impossible for you to forget you're watching an actor reading lines. Even worse is how anxious he is to be seen as sexually attractive—the yuck constantly intrudes on the experience.
Someone painted him on tumblr..
He'll never have any clear picture of his lack of ability at acting, because his fans blanket him with praise, fawning over everything—including praising his acting. I think this is often because many of them are trans, so they live vicariously through his relative success, as a mirror for their own trans narc. (This is why they turned on Contra: who absorbed their praise graciously enough, but then gave criticism back.)
Olly is so weak-willed that he'll always prefer to listen to people who flatter him—rather than seeking good constructive criticism, which could give him the motivation to second-guess himself and actually try to develop any abilities he has.