For one thing, I believe that people should only judge the work under the context of the album itself. Sincerity in cases like this can only be verify by external sources.
I also believe an artist should be judge by it's effect it has to the listener and not to the artist itself. Whether Tom Waits is an alcoholic or not and whether the song is personal to him is irrelevant, what relevant is whether it means something personally to the listener. I can't exactly judge because I'm not an alcoholic but if someone who is an alcoholic and relates to the song, it shouldn't make a different whether the songwriter had personal experience with the issue because a song should be predominantly judge on its impact on the listeners.
I also think that it's silly to dismiss "acting" as a negative. It's like saying I don't watch movies because all the actors playing the character are insincere and they aren't really like that.
I also have a belief that people have a spectrum of personality attributes and characteristic inside them.
A good actor/actress are people who are able to channel attributes that's already inside them even if they are attributes they never or rarely express in "real life". In a way, a person is never really "acting" rather all the different and contradictory personality attributes are a part of them even if it is hidden inside.
Lastly, songs that aren't autobiographical and have constructed stories and character can often be sincere. As a fellow songwriter, when people ask whether my songs are "personal", I will say that the stories aren't real but the emotions are. I've written a song about a character murdering someone after getting drunk and losing their temper due to a small thing.
Now have I ever murdered someone, well of course the answer is no but have I ever lost my temper and overreact to a small minor thing and felt guilty about it afterwards wondering why I got so mad about it in the first place. Well the answer to that question is yes. So a lot of songs aren't strictly personal and yet still can be sincere and heartfelt at the same time.
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