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MacDraw and Freehand.

I know there are modern vector/bezier-drawing alternatives, like OmniGraffle and Sketch and Affinity Designer. But both MacDraw and Freehand balanced functionality and simplicity and directness so well. In MacDraw, I could make technical drawings really quickly. In Freehand, I could do everything I could do in Illustrator, but with much better grid-snapping and typography. And I loved its 'morphing' tool (it wasn't called that), where you could take two objects (even type) and it would interpolate them and make these beautiful shapes.



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