High-back, leather executive chairs that let you lean backward are really cushy (and expensive), but you can achieve the same effect and not (totally) burn a hole in your wallet with the $500 Attitude Chair.
Unlike conventional seats, this contraption by Deger Cengiz is fitted with two additional legs. In normal upright position, these legs won't touch the floor. But as you lean back, they roll out to replace the two front legs that have just been lifted off the ground.
We're assuming the pair stops at a fixed angle to prevent you from tipping over. While you can't really play executive in a wooden chair like this, at least you won't embarrass yourself by falling backward.