I don’t think it would be difficult to follow but it wouldn’t exactly be a place to start. Emil Cioran was a philosophy academic who eventually rejected philosophy and became more of a poetical essayist. He's primarily known for his beautiful and dark literary writing style. Read him if you want, sure (though if you're depressed maybe skip it - taking care of yourself and manage your own resources and ability to cope with dark thoughts is important to living with such things) - but I don't think he provides a jumping-on point for other philosophy, nor do I think he would want to. He’s his own thing.