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These are the titles that I keep coming back to and watching again and again over time. I do make changes to this list from time to time as my tastes change and I get introduced to new titles. I wanted to make a separate list of titles that I especially like, regardless of how I thought they should be rated.

Personal Favorites Rating
Azumanga Daioh (TV) Masterpiece
This series is just plain fun. Comedy anime can be pretty hit or miss for me, but I was laughing out loud a lot while watching Azumanga Daioh. There is no big overarching plot, but the format of following the girls through their 3 years of high school and all the goofy things that happen to them works well. I very much liked the main characters as each one was well developed and all got their moment in the spotlight throughout the course of the series, while the supporting cast also added variety and some great gags. As someone who loved his time in high school, the ending of this series really got to me too. It captured very well the frantic rush to graduation and everything that goes with it -- preparation for college, celebrations with friends, finals, and the bittersweet realization that while finishing high school is a great accomplishment it also means the end of a wonderful time in life where you get to spend every day with friends and don't have all the worries of the adult world pressing in quite yet.
Cowboy Bebop (TV) Masterpiece (dub & sub)
I'm not sure what I can say about Bebop that hasn't been said 100 times already by 100 other people, but I'll just mention why it's one of my very favorite anime. With "Bebop" in the title, you would expect great attention to be given to the music, and that is certainly the case. Yoko Kanno's soundtrack is varied in style but consistent in its high quality. I loved it so much that I actually imported the special 4 CD complete soundtrack boxset from Japan. It ended up costing me more than the anime series did, and is still the most expensive CD set I have ever purchased but it was worth it. I don't normally like a highly episodic series like this as much as I like series that have a continuous storyline developed over the course of their entire run. But Bebop is just so well done and the individual stories are so good that I didn't really mind the format in this case. One thing that I thought was interesting was that during the course of my first viewing of the series I didn't think I had developed a very strong sense of attachment to any of the characters until the last four episodes when I found that pretty much without my realizing it they had woven such complete and compelling backstories that I was fully hooked in and hanging on every moment to see what was going to happen. I love the fact that although the show is mostly episodic that little by little, here and there, they found a way to fully flesh out Spike, Jet, Faye, and Ed so that you care very strongly what happens to all of them at the end. The stories that dealt directly with with character development and backgrounds were also among the strongest of the series. I think my very favorite episodes are the two part Jupiter Jazz story that is the midpoint of the series. Of course, no comment on Bebop would be complete without mentioning the ending. All I will say about it is that I thought it was perfectly suited to the story and that the actual execution of the final three episodes are as near to the perfect example of how to wrap up an anime series as you are likely to find.
Crest of the Stars (TV) Excellent
El-Hazard: The Magnificent World (OAV) Excellent
I will be the first to admit that I probably like El Hazard more than any objective, rational person would, but it just works for me. Looking at some of the individual elements of the show, the collection of clichés seems like a recipe for disaster: people transported from our world to a parallel dimension where they have to help save the world, the childhood friend with secret feelings for the main character, the tough on the outside yet sensitive on the inside girl, the aging woman desperate to find a husband, the princess in distress, a hot springs episode, a harem-type story element, a crazy high school rival, not one but two ultimate weapons of mass destruction, GIANT BUGS…! But somehow, some way, it all fits together to make a funny, touching, and thoroughly enjoyable story. In the end, El Hazard is about overcoming the past, redemption, and not giving up on someone you love, all wrapped up in a wacky and fun package. This is a show that I have watched over and over, and I love it every time.
Gunslinger Girl (TV) Excellent
Haibane Renmei (TV) Masterpiece
Kino's Journey (TV) Masterpiece
Kino's Journey is a wonderful series of mostly self contained episodes that follow the travelers Kino and the sentient motorcycle Hermes. In traveling from country to country, Kino and Hermes experience many different ways of life, meet diverse people, and generally observe the human condition. This is truly a fantastic series. Each episode presents a story that looks at a different aspect of humanity and without being too preachy or over the top gives the viewer something to consider while at the same time being entertaining. The animation and music are both understated and wonderfully support the storyline. The issues considered during the series are in no way original or unique, but the stories used to examine these ideas are very creative and well thought out. Using Kino and Hermes in the role of observers gives an outsider's perspective on the events that occur, and sometimes the things they take away from their experiences are not necessarily what I would have come up with on my own. I like that this series can entertain while at the same time providing material to ponder and touching on themes that relate to our own world and experiences. It also provides some touching and emotional scenes during the course of its run. While some few people will probably find this series to be dull (if all you want is fanservice and explosions then this is not the place to look) I simply can not recommend it highly enough to anyone that doesn't mind their anime to be thought provoking as well as entertaining.
Lunar Legend Tsukihime (TV) Excellent
Mushi-Shi (TV) Masterpiece
Rurouni Kenshin: Trust & Betrayal (OAV) Masterpiece
The prequel to the Kenshin story portrayed in the TV series. No reverse blade sword, no oath of not killing, no Kaoru, Sano, or Yahiko. You won’t see any comedic moments or exclamations of “oro” from Kenshin. As would be expected in a story about an assassin in the midst of war, there is a lot of blood and some very gruesome deaths. This is the story of when Kenshin was the hitokiri battousai, and it lays the groundwork for a much deeper understanding of how he became the man we see in the television series. While seeing the television series is not required to make sense of this OAV, I saw it after watching the first two seasons of the TV show, and I really do think it has more impact that way. After spending time with Kenshin seeing him try to come to terms with his past, the story of that past only glimpsed briefly during the TV episodes is very powerful. The story has a sense of inevitability about it because you already know where Kenshin ends up years later, but while you know in general how things are going to end you don’t know the details of the story. The combination of the plot, animation, and music does a great job of involving you in the tale of Kenshin's early life, and you can't help but develop a strong attachment to the characters and really feel for their struggles and their desire to find just a bit of happiness in a chaotic world. The dichotomy in the pace of the storytelling, which goes from the frantic and well animated fights to the quiet and reflective moments Kenshin spends with Tomoe helps to illustrate Kenshin’s internal conflict. He wants to help create a world where people can live in peace without fear of violence, yet to accomplish this goal he ends up committing repeated acts of horrible violence himself. With this story we get a much better understanding of who Kenshin really is, and his character gains a depth that the TV series alone did not impart. This OAV is a great example of things done right in an anime, and it is the gem in the collection of animated Kenshin works. This show left a big impression on me, and is still one of my very favorite anime works.
Spice and Wolf (TV) Excellent
Spice and Wolf II (TV) Very good