1. Shikamaru- he's as lazy as I am! He's funny as hell and his fights are so mind-bendingly complicated and his victories sheer genius! A mediocre guy otherwise only accents how friggin hilarious his massive IQ (and puts all that grey matter to good use)
2. Kabuto- this is the one baddie I can't figure out to save my life. The hospital scene was cunning and slick and I like how you're never going to be sure how faithful he will be to Orochimaru in the end. Wish he had more screentime after Chuunin Exam...
3. Jiraya... the man is a huge perv and still kicks ass! Plus Naruto owes him just about everything when it comes to fighting
4. Haku- Yes he was a homo but this kid had a heart of gold and was so damn calm and badass all at the same time! One of the most complex characters I wish I'd seen more of in an anime.
5. Rock Lee- hate his personality, but his fights are probably the best action scenes in the show bar-none.

Honorable mention: Kakashi for his laid backness, Gaara for his messed up past, Neji for his brown hair, Tayuya for her cursing, Kiba for being an all around jokster/asshole

Bottom 5,
#5 Orochimaru- i just cant stand his voice... and he took forever with the 3rd...
#4 Whats his name from that stupid race mini-arc! - stand up for yourself you pathetic worm!
#3 Itachi- YAWN! Oh I'm sorry, were you trying to motivate plot development? So far the most one dimensional character on the show... I want to see how much I'm capable of and then keep going up! Maybe if he weren't set up so much as a main villain. Oh, and story is interesting, but flashbacks are old and sick of seeing them
#2 Naruto- not all the time, just a majority of the time. For all the stuff he's gone through he hasn't shown too much development. Still the headstrong, stupid, impossible to kill do-gooder. So pure and naive it makes me sick. As narrow minded in his goals as Itachi. Can be funny though.
#1 Sakura- I also had high hopes for this character early on. Thought she could be the strategist, peacekeeper, support for genjutsu part of the team. All she's done since the Chuunin Survival Round is complain, cry, be worried, make others worry, get in the way, oggle Sasuke and then rinse and repeat. Inner Sakura hasn't manifested anywhere, she's thankfully been put on the back burner and is only important because Naruto is fond of her.