To make someone cry; to move someone to tears, often by touching their emotions.
あの映画は最後の場面でみんなを泣かした。
That movie made everyone cry at the final scene.
彼の手紙が母を泣かしてしまった。
His letter brought his mother to tears.
子どもを泣かすつもりはなかったが、叱り方がきつすぎた。
I didn't mean to make the child cry, but I scolded too harshly.
To grieve or cause deep sorrow (somewhat literary/archaic usage), to make someone mourn or lament.
戦争は多くの家族を泣かしたという記録が残っている。
Records remain that the war left many families grieving.
親の死は若者を深く泣かすことがある。
The death of a parent can deeply grieve a young person.