Cowboy literally just means rancher. It was not a particularly good job in the wild west and it’s only marginally better now.

Samurai were well respected, well paid, and had social status. The downside is that they needed to kill people or die trying when their boss said to, which doesn’t sound like fun to me.

Pirates also have the problem of having to do violence on a regular basis, but without the glamour and respect of being Samurai.

All in all, I’d probably choose samurai.