Tricky, but good translators, especially those who are competent writers in their own right, can do it.
Harry Rowohlt could do it. Among a lot of other works, he translated Shel Silverstein and absolutely nailed it.
He also used to contact ‘his’ authors whenever possible and bombarded them with questions about the tiniest details, just to get it right.
When he was about halfway through translating Frank McCourt’s Angela’s Ashes he had a bit of a writer’s block and sent a fax to McCourt, suggesting to cut things short by killing off the main protagonist. Despite this, Rowohlt and McCourt became close friends until death parted them. They used to drink together at literary conventions and sing Irish songs; the stories are legendary.
There is also the joke about a reader urging a friend to buy a particular book’s German version as “the original looses a lot in the translation”.