Jessica Simpson may be a "has been" in terms of her music career, but she still makes millions every year from her shoe and clothing lines.
I agree about Hilary. I don't think she truly cares about the entertainment business as much as other Disney stars have/do. Especially now that she has a family.

I'm sure she's financially stable for the rest of her life, considering she can still get into acting jobs in the future.
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"Remember, don't let others dictate your music taste. If you like whatever you're listening to, keep listening to it."