The Riskiest Single of All Time

I definitely think Hello Kitty. It was a sound she had never done before and while her fans in Asia loved it, it didn't really translate to the rest of the world. It also risked her image and reputation a lot (especially the video) by making her look immature and then there was the whole racism controversy. On top of it the single failed on the charts (except maybe in Asia), the video did go viral, but for all the wrong reasons. In the end it really didn't help her career at all, but actually probably damaged it more.

I would put Girlfriend at a close second because it showed off a bratty and more pop side that she had never showed before and it was a complete 180 from the mature image she showed with UMS. It alienated a lot of her fans and as we know it kind of sealed her fate further down the line of having to make similar singles. But the only reason I don't rank it as the riskiest single is because unlike HK it actually was a huge hit, still her biggest to date, and it really solidified her place as a popstar. It also was still a pop rock song and while it had kind of a new sound, it wasn't as different for her as HK was, and GF is actually a very well produced pop song. I also don't think it really damaged her image and career as much as HK did. Once people got over the change in her style a lot of people liked it and she gained a lot of new fans, even if she lost some of the old ones. HK didn't gain her any new fans.

Haha for what it's worth I consider some aspects of UMS to be immature but I know generally her fans consider that era and album to be "mature" especially in comparison to TBDT. Maybe "serious" is a better word.

I quite agree with you. Girlfriend was risky due to being too pop for her fans' taste, although sonically it wasn't more pop-punk than pop. The fact that she alienated a big part of her fanbase (and she probably knew it would) definitely made it a risky single, because if it hadn't been as successful as it were, her career could've been severely damaged in all aspects back then, kind of what she is now. But at least she had a few more years of success and was able to get some extra money from it, even though I don't think Girlfriend/TBDT was really good for her in the long run.

HK was even worse, because it was even more controversial, she got backslash for the wrong reasons and it alienated her fanbase and GP even more. It was kind of the last nail in the coffin

As for UMS being "mature" or not, I would consider it more meaningful, honest and (as you said) serious. LG was more mature, and GL was as well; the latter approached a breakup in a more grown-up mature way than UMS ever did.

Honestly no. In fact none of Avril's songs are THAT different from each other. As diverse as pop music can be, it has its boundaries.

Nevertheless, the small difference between HK and GF made the former more risky than the latter imo.

exactly.

That's why I voted for Girlfriend.

Ofcourse, Hello Kitty

Girlfriend was a huge risk. Although it's not quite my style (I can't remember the last time I willingly listened to it), I have to respect the fact she did something so out of her comfort zone. She not only did it but she dominated the entire pop genre with the song that year. All the fans who felt alienated by her sudden change in direction had no choice but to hear it on a consistent basis for a while and when you think about it, The Best Damn Thing had a very distinct sound, you could easily tell it was still Avril. It was risky but it worked out very well in her favor..

Hello Kitty got my vote though. It was different; and different as it was, it did nothing to help her career. It generated a lot of buzz but was it really worth the risk or the cost? Avril is happy with the song and that's what matters first but I can't blame people if it made them turn away from her.