Tough one, but I have to go with TPatF, simply because it used jazz which isn't very popular with the younger audiences Disney caters to.

''Savages'' is a pretty dark song

The characters don't really sing the songs in this movie, they're mostly played in the background, and it's only 2-3 songs during all of the movie (and placed very far from each other, one playing at the start and the other at the end), serving more as montages than anything else. The film's not really a "musical" movie per se.

^I would say brave takes the LEAST risks then

Also I picked at random, I'm not sure.

Hard question...but here is my reasoning:

Beauty and the Beast, Aladdin, Pocahontas and Tangled don't really take a risk because the soundtracks are all created by a proven composer. Menken is great, but after TLM he was certainly the safe choice. All those movies repeat a proven formula.

Frozen's style is too much oriented on the popular to count as risky. I mean, this movie has a Lion King style opening, then goes wicked and finally throws in some funny song, it's like it is trying to appease every kind of taste.

And Brave is done in typical Pixar-style, the only risky thing about it is that they didn't use Henry Jackson or any of the Newman's for it.

Snow White and Cinderella are typical early Disney productions, in which different songwriter were working on a movie, whose work was then combined into a soundtrack (that is especially true for Cinderella, less for Snow White). Nothing against the approach in principle, but it does not really allow for bold choices.

Now, the choice of Jazz for Princess and the Frog is perhaps a little bit unusual for a Disney Princess movie, but not for a Disney movie in general, but it was a choice based on the setting and they did pick Randy Newman, plus, the soundtrack ended up a little bit pedestrian.

Which leaves Sleeping Beauty, The Little Mermaid and Mulan.

That is really a hard pick...Mulan kind of sticks out because of the total lack of a love song, plus, the score and the songs are not by the same composers, and therefore slightly different in style. But this is also something one could see as weakness.

The Little Mermaid is naturally THE movie which created the whole Animated Broadway Movie concept...it is also pretty bolt to mix in Sebastian's more raggy-style songs into it, and that in a way that it never feels grating but fits. That's really well done.

On the other hand though, Bruns had to rewrote the work of one of the most famous composers of all time to fit Sleeping Beauty...he repurposed pieces, and created a new soundtrack in which everything goes seamlessly together while respecting the integrity of the original. And that is in a lot of ways more difficult than create something totally new. So he edges Menken and Ashman out...just.

I was going to go with The Princess and The Frog, but then I read Swanpride's comment and she has a really good point. Close call but I've gotta go with Sleeping Beauty.

I read SwanPride's comment and it inspired me to pick the Little Mermaid. I don't think it's that difficult to take already existing music and add lyrics to it, especially when the score is already laid out for you, you've just gotta piece it together. Harder to make up your own stuff that's appropriate to a film project.

I'm surprised not as many people chose this, I understand, the music isn't very risky, but just look at the lyrics in "Savages"! The descriptions they used to describe both sides has a risk of causing controversy.

and Sleeping Beauty, Princess and the Frog and Brave.

I also was about to go with PATF, but SB makes more sense now. but after that, definitely that jazz and gospel-style music from PATF.

Brave's is a little different- most of it MUCH more realistic to the time period than Disney has done in awhile (cough Tangled) but overall there's nothing terribly standout about it so I don't think it was a big risk.

Yeah, I got a little bit carried away...I recently wrote and article about the Disney Composers (link), so I spend a lot of time looking up who did what why and how the end result sounded.

And Brave