Is this inequality always true? $$ \bigl\lvert\,\underbrace{\sin(\sin(\cdots \sin}_{N\text{ times}}(x)\cdots))\bigr\rvert\le\bigl\lvert\,\underbrace{\sin(\sin( \cdots \sin}_{N-1\text{ times}}(1)\cdots))\bigr\rvert $$
I think so, for example for $N=2$ we have:
$|\sin(x)|\leq 1$ therefore $|\sin(\sin(x))|\leq |\sin(1)|$
Sorry, but I remember you that the $\sin$ function is strictly increasing only in $Z_1=\displaystyle\bigcup_{k\in\mathbb{Z}}\left[-\frac{\pi}{2}+2k\pi,\frac{\pi}{2}+2k\pi\right]$ and therefore: \begin{equation} \forall x\in Z_1,\,\sin(\sin x)\leq\sin(1),\,1>\sin 1>0; \end{equation} while in $Z_2=\displaystyle\bigcup_{k\in\mathbb{Z}}\left[\frac{\pi}{2}+2k\pi,\frac{3\pi}{2}+2k\pi\right]=Z_1+\pi$ the $\sin$ function is strictly decreasing and therefore: \begin{gather} \forall x\in Z_2,\exists y\in Z_1:x=y+\pi\Rightarrow\\ \Rightarrow\sin(\sin(x))=\sin(\sin(y+\pi))=\sin(-\sin(y))=-\sin(\sin(y))\geq-\sin(1). \end{gather} From all this: \begin{equation} \forall x\in\mathbb{R},\,|\sin(\sin(x))|\leq|\sin1|, \end{equation} and by induction you can prove the claim.
Is it all clear?