I have a friend I want to introduce to anime but I don't know where to start. I'm thinking Cowboy Bebop would be a great starter. It's funny, action packed, serious in a good way, well voiced, beautifully drawn, and intense. But after that, I'm stuck. Sailor Moon will always be my #1 favorite anime, but as a middle aged guy, I don't think he'd be into it (err, or maybe he would... D: ).
What series or movies may you suggest I show him to get him into the game?
If he likes Bebop, perhaps stick to series in a similar vein until he's a fan of the medium and willing to explore genres. Baccano, Black Lagoon, Darker than Black, GitS: SaC, Samurai Champloo, etc...
Do you know what kind of TV/movies he enjoys normally? That would be helpful, just show him anime that are similar.
Haibane Renmei
Coyote Ragtime Show [ducks]
Black Lagoon (as >>2 mentioned)
Trigun
Big O
Gunslinger Girl
Serial Experiments Lain
RahXephon
Read Or Die
Shakugan no Shana
Fullmetal Alchemist [ducks AGAIN]
why not start him off with a movie?
>>3
MVB detected!
Sci-fi:
Planetes is a must watch, then, and I'll reiterate DtB and GitS: SaC. I don't really like Trigun but that might be a good choice. Any mecha anime will do in a pinch.
Horror:
Hmm. Well, in my opinion, you don't know of too many horror anime because there aren't too many that are good.
Boogiepop Phantom and Higurashi, possibly. Both of these are very weird shows though and I wouldn't show them to a beginning anime fan.
>>4 Serial Experiments Lain
That is not a good idea for a starter =.=
>>9 depends on how much a thinker the person is
Boogiepop Phantom [Seconded]
Nods
Chobits is a pretty good starter anime.
Perfect Blue
Escaflowne
>>10
It really does. Lain is one I have shown with much success to anime neophytes who liked movies like Memento or The Usual Suspects.
>>13
I know people who absolutely hated Chobits, so I'm not sure it's as good of an idea as you think. Besides which, for a middle-aged guy (such as the OP is dealing with), the romantic comedy genre might not be the best. Among CLAMP works, xxxHolic might be better for that case.
The Big O [Seconded]
Kino no Tabi
Akira ofcoure, and Ghost in the Shell.