What to watch--Anime

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I want to start watching Anime on Viki. Which ones are best for crossovers/shipping?

I know heaps of anime, but not a lot about "Viki", looking at their site seems to only show only a few pretty old titles, so I would probably recommend using a different site, AniLinkz is what I use.

Following your other criteria:
If you mean "crossovers" as in shows that interact with each other, I can't think of many strictly true answers. Although what does come to mind is CLAMP, which apparently has series crossovers, a likely one to have seen before would be Card Captors which apparently has made crossover appearances in Tsubasa Reservoir Chronicles with other series like Chobits. I am mostly aware though of Kobato that had actual crossover episodes and characters from CLAMP shows.

If you mean "crossovers" like references to other things like pop culture and other anime? There would be Hayate the Combat no Gotoku, Haiyore Nyaruko-san, Lucky Star, Seto no Hanayome, and maybe Choujigen Game Neptune The Animation if you were into game culture.

If you meant "crossovers" as in something popular in the fanfiction side, well I can't be too helpful, it would probably best to search that on say google. I get THIS PAGE from searching fanfiction, but I am not really into that.

As for "shipping", that I can probably help with.
Free! was a recent big success, especially with female viewers, due to all the guy on guy ships.
Maybe Fairy Tail, that has its fair amount.
Hetalia is apparently popular, but I don't know much about it.
And I can think of Magical Girl Lyrical Nanoha which has its shipping, and popular with fan crossovers. Which I would also recommend Puella Magi Madoka Magica, which is pretty popular and garnered the same attention.

I hope that I was helpful somehow.

Here are some anime crossovers and ships that I've come up with. Hopefully it might give you some ideas:

Blue Exorcist x Madoka Magica

Rin x Madoka

Shiemi x Madoka

Yukio x Homura

Bon x Kyoko

Izumo x Kyoko

Blue Exorcist x Panty & Stocking

Rin x Panty

Yukio x Stocking

Shiemi x Brief

Rin x Scanty

Yukio x Kneesocks

Amaimon x Stocking (I didn't invent this, but it's popular)

Evangelion x Madoka Magica

Shinji x Madoka

Kaworu x Homura

Rei x Homura

Asuka x Kyoko

Elfen Lied x Higurashi no Naku Koro Ni

Lucy/Nyu x Mion

Nana x Rena

I have to go run some errands but I really hope I gave you some good suggestions.

Attack on Titan!