Dude Ore Monogatari is super adorable. It's a great one! And yeah it's not too old but it is from around that time.
Also I'll recommend Sk8 the Infinity for anyone who likes sports anime at all. I didn't use to be super into them but some of them get me. Especially the more extreme sports ones like this. Happy to say the characters are fun and it's go just enough ridiculous shit so far to really get me. They have only shown brief glimpses of the villain so far but what they have.... omfg.... it looks like we're about to get a skateboarder version of DIO. Even his voice sounded similar and the vampire thing is totally there. One of the main characters is a half canadian snowboarder learning to skateboard now.... I feel like I'm starting to see a trend with canadian stereotypes in anime lately....
Also I'll recommend Sk8 the Infinity for anyone who likes sports anime at all. I didn't use to be super into them but some of them get me. Especially the more extreme sports ones like this. Happy to say the characters are fun and it's go just enough ridiculous shit so far to really get me. They have only shown brief glimpses of the villain so far but what they have.... omfg.... it looks like we're about to get a skateboarder version of DIO. Even his voice sounded similar and the vampire thing is totally there. One of the main characters is a half canadian snowboarder learning to skateboard now.... I feel like I'm starting to see a trend with canadian stereotypes in anime lately....