I think we have some pretty good discussion of this question already from earlier Questions 729, 1497, 1806, 2111. It's a fascinating question certain musicians and artists have raised through their work (just as you imagine), and all the more interesting for there being no compelling way of reaching an answer.
It is surely possible that a person's music reflects his or her personality and self, and possible that, by listening to this music, you gain insight and understanding of him or her as a person. But I would be very reluctant simply to assume that this is so. Here are three reasons why.
First, the inference from artwork to artist's personality is hardly straightforward. It is rarely true that only a very specific kind of person could possibly have produced a certain set of artworks. And there is little reason to believe that we are good at tracing whatever such connections there may be. I have often been stunned at seeing an artist I greatly admired say silly things in interviews, often including silly things about his or her own artworks.
Second, we live in a world of commerialized art, where a single popular song can pull in millions of dollars. A great deal of money is therefore spent on fine-tuning songs to fit a certain free-spending segment of the audience. To put it bluntly, many an artist is "designed" by marketing specialists who try to manage every tiny aspect of her or his public persona (including appearance, of course, but also little missteps, scandals, and all this) for maximum sales impact. Singers are (also) commercial actors, playing roles for a paying public.
Third, the claim or belief that you know and love this musician as a person is of no real value to you. Imagine, for example, that you have an opportunity to meet him. He does not know you; and for any sort of meaningful relationship (including love) to develop between you, you would need to spend time together, walking, talking, dancing, dining, and such. As he would get to know you, you would have ample opportunity to test and perhaps revise your earlier hunches about his personality. It's just so much better for two people to fall in love with each other than for one of them to do it all by herself... . -- In other words, there's no good reason to gamble on the assumption that you understand him.