Kakashi for me I was all head over heels for over 15 years. XD

When Kakashi was firstly introduced the drawing was a bit 1990's manga. But his look has improved throughout the series to 21st Century.

One of the best things I like Kishimoto's work that he actually showed each characters' growth throughout the series without you notice and you basically grew with them. Unlike how Ash left his small town and somewhat 100 years later still 10 years old.