At the point at which you hit 'submit' you will probably have assented to some kind of copyright agreement. Two different journals cannot both hold the copyright of your article, so that is a practical reason why it's not permissible.
But, as others have said, the process of reviewing a manuscript for publication is not trivial, and if anyone involved discovered that their efforts could be rendered pointless because another journal published your work first, you wouldn't end up with many friends in publishing/in your field.
I agree with the strategy of aim for the highest feasible journal and work your way down. But do be honest with yourself about what is feasible - otherwise you'll have to go through multiple rejections. Always good to get guidance from your elders on this one.