Whether you like it or not, time is a constant and things change as does taste and needless to say these characters haven't aged well.
There's no set order either.
1. Gourry Gabriev from Slayers
Slayers is a fantastic series of very capable characters, pity Gourry isn't one of them, the sheer gap between Lina Inverse and Gourry in power and abilities make for grim reading for the blonde swordsman, not helping his case is trying to be chivalrous to a character that doesn't need help and spending way too much time being the butt monkey.
2. Chang Wufei from Gundam Wing
I was surprised how well Gundam Wing aged but then lose it when you see how much of a misogynist Chang Wufei is, while the franchise isn't short on dramatic fighting types and you can make a decent case for the G Gundam cast to appear on this list also, at least G Gundam wasn't belittling the female characters it did have.
3. Louise Françoise le Blanc de la Vallière from Familiar of Zero
Flaunts her title as an excuse to abuse the lead character, need I say more.
4. Kagome Igarashi from Inuyasha
You could make a case for Akane Tendo but some of her tsundere outbursts are justified considering the company she's around, Kagome doesn't have that excuse, at first Inuyasha did need keeping on a leash but when Kagome practically abuses it for the whole run of Inuyasha it doesn't leave me with much to like.
5. Naru Narusegawa from Love Hina
Get used to the tsunderes, they're usually my first target for these lists.
Naru after a while was really only abusing Keitaro to hide her own insecurities, it's hard to watch at times.
6. Lynn Minmay from Macross
She is literally just eye candy and every sci-fi idol has surpassed her even within her own franchise.
7. Belldandy from Ah My Goddess
Has all the personality of a domestic doormat and easily one of the most beautiful female characters of her era, yet I hate every story that focuses on her.
8. Ryo Saeba from City Hunter
Bad ass or not, you can't get away with Johnny Bravo womanizer behaviour even in anime, Ryo is a frustrating character to watch at times.
9. Haruhi Suzumiya from Melancholy of Haruhi Suzumiya
I haven't really forgiven her for some of the worst aspects of anime fandom, that will require it's own list in the future.
10. Hilary Tachibana from Beyblade
It's thanks to Hilary that Beyblade never really evolved beyond a boys club. It basically boils down to toy anime not being very inclusive, something that hasn't changed much even today.
