Destiny's child-No no no (innovative daring & risky. Beyoncé created a new style of singing)
Destiny's child-Bills Bills Bills (a breath of fresh air in the boysband/mickey house preteen singers)
Destiny's chil- Survivor (a song with a message finally on the radio)
Beyoncé-crazy in love (first song wih a horn section to smash since the 70's)
Destiny's child-lose my breath (Beyoncé bringing Darkchild back)
Beyoncé-Deja vu (Beyoncé bringing Jazz music back on the radio)
Beyoncé-if I were a boy (Beyoncé bringing pop/rock music back on the radio)
Beyoncé-RTW(girls) (Beyoncé bringing African music to US radios)

Would "Gimme More" count?

If you think that WFL is risky, I have no idea why you would think WANEGBT is not risky.

Dying over the responses in this thread

Skyscraper and Russian Roulette

Yes, Yes, Yes, Yes, Yes, Yes, Yes, Yes.......

born this way received nearly universal positive reviews not as far as being acclaimed but almost all reviews were positive

Some of your choices aren't even risky. Releasing a very pop single like Taylor's is not risky at all. It's just to get an easy hit. Oh and some of those Beyoncé singles? IIWAB isn't pop/rock nor risky. It's an r&b/pop ballad, somewhat comparable to Irreplaceable. RTW is not "African music" just because of the drums, have any of you heard Diplo's work? Drums =/= African music.

And now back on-topic. When I think about it, there aren't any good examples for risky singles who smashed. A lot of them do somewhat OK, like Russian Roulette. That single was risky because of the Chris Brown story and because she has never had a slow song as a first single. But a lot of the risky singles flop, like Nelly Furtado's Bigger the Better.

SexyBack was definitely risky. Releasing at a time when dance-pop was not dominating radio, and the song having a weird spoken repetitive chorus. I remembered my friends trashing it when they heard it for the first time, but soon growing to love it once it became a hit.

We Found Love was risky? WE FOUND LOVE???

These are the songs that come to my mind:

Kelly Clarkson - Mr. Know It All
Demi Lovato - Skyscraper
Justin Bieber - Boyfriend
Train - Hey Soul Sister
Foster The People - Pumped Up Kicks

Born This Way.

Wait, that's what it's about?

Becvause its not country at all, and she has a large country stanbase. And having the country remix not being the itunes version put a lot of her fans off

And in what world is WANEGBT RISKY?

How is Born This Way risky when it's the same kind of dance music she was doing for the better part of two years before?

Writing like this
Dosen't take the fact that "Never" is one of the most safe singles ever its a sure hit

A REAL risk would be...

Ne-Yo's "Closer." It was a risk because Ne-Yo had just become a big hit in R&B with his two previous albums. "Closer" was nothing like "So Sick" or "Do You." It was a straight up house track, but it was good and worked in his favor. Too bad doing dance trash has done nothing for his career in the long-run, though.