YOU SAID:

wow that was extremely bad dude

INTO JAPANESE

うわー、それは非常に悪い男でした

BACK INTO ENGLISH

Wow that was a very bad man

INTO JAPANESE

うわー、とても悪い男でした

BACK INTO ENGLISH

Wow, that was a very bad guy.

INTO JAPANESE

うわー、とても悪い奴だった。

BACK INTO ENGLISH

Wow, that was a very bad guy.