It's definitely a toss up for me. I think at this point I've seen The Melancholy of Haruhi Suzumiya more than any other series. It's pretty much my go to series whenever I'm down. It has it's issues, but I really like the characters
I've also watched both Boogiepop series and Bloom Into You many times as well
edit - adding D-Frag as well for feel good series I watch almost once a year
I can't stop rewatching the old Gundam OVAs like 0083 and 08th MS Team, something abvout everything down to the stunning OPs just drags me back every time.
On the other hand, I've started and never finished The Big O more times than I can count, and I've watched the first episode of Haibane Renmei sixty thousand times, and not one second of the series beyond that.
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Tell me about it! Every time I inevitably (re)pick it up I love the whole ride right up until fate throws me for a loop and I have to focus on something else and put it on hold. Repeat three more times. I have had more luck going slow and steady watching the OG sailor moon one ep a day.
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I am once again asking Gundam fans to watch Victory Gundam. :bernie:
Its Tomino at his absolute nuttiest and still manages to be one of his best shows.
I haven't seen those Gundam OVAs! I'll have to check them out. Gundam Wing was one of the first anime I got into when I was growing up (along with the rest of the Toonami block)