I may not be a religious man, but I definitely believe that to not attempt to excel in your vocation is a sin. To sincerely attempt it and still fail, though, is more of an occasion for pity than disdain, and that’s exactly why I feel so sorry for Ashlee Simpson. You might say she had a Salieri complex—here was a girl with brains, ambition, artistic vision and an impressive amount of courage, but with absolutely no talent to back it up. At least her sister Jessica had, if nothing else, a singing voice; Ashlee didn’t even have that. Watching her try to be a legitimate artist was like watching a mouse trying to lift a cathedral; she was never going to succeed (it’s a miracle she even had the few schlocky Pop hits she did), but you have to be impressed with the effort involved. This was the song that led to the scandal that effectively ended her Pop career, and while I gather she’s been exonerated of the accusations it engendered (not that it saved her career), the song itself demonstrates why she had no business being a singer. It was a failed attempt at raw drama in the vein of artists like Pink and Kelly Clarkson, and hearing her rasp her way through this ugly, abrasive trainwreck with its bizarre, off-putting lyrics is a complete demonstration of all the necessary skills she didn’t possess. It also demonstrates her heartbreaking determination to try anyway…say what you will about it, this isn’t the careless hackwork her sister generally released during her singing career. Most of the bad Pop singers of Simpson’s era failed artistically because they didn’t try and still managed more commercial success and critical respect than she did, so it’s hard not to lament what could have been if she only had the talent to make her obvious vision a reality.
Verdict: Bad, but in a sad way, not in the usual contemptible sense.