Evaluate $\int_{|z|=4}\tan z\,\mathrm dz$
$\tan z=\frac{\sin z}{\cos z}$ there is a a simple pole at $z=\frac{\pi}{2}$
$\operatorname{Res}(f,\frac{\pi}{2})=\lim_{z\to \frac{\pi}{2}}(z-\frac{\pi}{2})(\frac{\sin z}{\cos z})$
$\operatorname{Res}(f,\frac{3\pi}{2})=\lim_{z\to \frac{3\pi}{2}}(z-\frac{3\pi}{2})(\frac{\sin z}{\cos z})$
How to continue ?
You have\begin{align}\operatorname{Res}\left(\tan z,\pm\frac\pi2\right)&=\lim_{z\to\pm\frac\pi2}\left(z\mp\frac\pi2\right)\frac{\sin z}{\cos z}\\&=\lim_{z\to\pm\frac\pi2}\frac{\sin z}{\frac{\cos(z)-\cos\left(\pm\frac\pi2\right)}{z\mp\frac\pi2}}\\&=\frac{\sin\left(\pm\frac\pi2\right)}{\cos'\left(\pm\frac\pi2\right)}\\&=-1.\end{align}Besides, $\pm\frac\pi2$ are the only poles in the disc centered at $0$ with radius $4$. Therefore\begin{align}\int_{|z|=4}\tan z\,\mathrm dz&=2\pi i\left(\operatorname{Res}\left(\tan z,\frac\pi2\right)+\operatorname{Res}\left(\tan z,-\frac\pi2\right)\right)\\&=-4\pi i.\end{align}