I've been on a tear man. Complete 180 on Anime.
First one I got into was Samurai Champloo. Masterful show, hated the filler episodes, but the core of the show itself was perfection for me. Loved every bit of it, including the incredibly bittersweet ending.
Then watched Michiko E Hatchin. Really enjoyed that one too. Thought the ending was going to go somewhere else, but it was satisfying nonetheless.
After that was "Haven't You Heard? I'm Sakamoto". It's about a dude who can do no wrong, everything he does he does in the most nonchalant, stylish way possible. This was hands down one of the funniest shows I've watched in my life. Uproariously funny, I actually got my girlfriend to watch it with me. And she is hardcore against subtitle anime, but this show was golden. The ending hurt so bad, you really just wanted it to go on forever.
Just started watching To Be Hero today. A little raunchy, but it's still pretty funny. You've gotta be a mega weeb to be able to watch this show tho. The subtitles FLY by, and sometimes theres two characters talking at once.
Next is One Punch Man, then Cowboy Bebop.