YOU SAID:
He looks up grinning like a devil.
INTO JAPANESE
彼は悪魔のように笑いながら見上げます。
BACK INTO ENGLISH
He looks up with a devilish grin.
INTO JAPANESE
彼は悪魔のような笑みを浮かべて見上げる。
BACK INTO ENGLISH
He looks up with a devilish grin.
That didn't even make that much sense in English.