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I am each day making the art in illustrator more complete and now comes the time where I decide to invest in an animation program/route. I hear at times for people to use Toon Boom but the problem is I don't see a ton of tutorials and it seems like it's more for hand drawn animation. So, I'd use AE for example to draw out 15 or so frames for my robot rolling animation, adjusting the lines in different areas and then use a script to export that to a spritesheet I suppose. The main thing I want to avoid is the stiff puppet animation I see in many flash animations. So, do you guys have any thoughts on starting on either of these two programs for 2D animation or tips in general in relation to this process?

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The stiff puppet animation you see is not a result of flash, but rather enabled by it. I've seen really great animations done in flash, it just depends on how you use the software. If you make an arm movieclip and put it on a spline or just rotate it in place then yes, you'll get the puppet animation. Flash has functionality to ghost previous and next frames, to help you draw smooth transitions. I've used it to draw pretty smooth stick figure animations before (my art abilities are limited).

I think the major difference you need to factor into your choice is the type of drawing you want to do. I find flash better to draw things precisely. If I need it do be symmetric, with equivalent angles on every side, flash does it better for me. For example, drawing tanks, cannons, spaceships.

Actually making them look good, artistically, becomes a challenge. Sure you can apply a simple gradient, but I find it harder to add the "finishing touches" in flash. I usually export to images that I finish in Paint.NET or something.

Of course, flash is very expensive. If you have access to it, or have lots of spare money, I recommend using it. Other wise, I have tried Toon Boom and it didn't seem that bad. I just was familiar with Flash and Paint.NET, so that's what I used.

I don't feel that flash will be worth it to you for the price. But you should at least download a trial and see for yourself.

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I haven't used Flash for a very long time, but I do remember it supporting 'tweening' which is where you move each vertex by hand for each keyframe and then Flash generates the inbetween frames. This is esstenially what Disney was doing for decades so of course you can achieve fantastic results with it. The downside is it's very time consuming. Programs like Anime Studio support a 2d version of the skin/bones animation found in 3d applications like Maya. A similar thing is called Puppet Warp in Photoshop CS5. In this you set up a skeleton behind your hand-draw art and then you can just move the skelton to where you like (within limits) and the art move with it, smoothly bending at the joins.

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