I think just about every time I've had characters look up I drew them looking up in a side profile. Getting the jawline to look right when at any partial-front or full-front-facing angle is just a pain. Even way back in art class when there was a model it still wasn't much easier. But hey sometimes you gotta try for the hard stuff!
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That's why I like using the Interview Cam, where they just talk straight at the viewer for a panel or two. Time to have more interviews!