Wit and ligne claire
Finally I took some time to do some research about that illustrator. The one who systemematically designs my favorite New Yorker covers, his name is R Kikuo Johnson. There is a twisted wit in his narratives which plays an intriguing game with his clean style highly influenced by the “ligne claire” straight from Europe (think of Tintin). Check his website, his work and interviews here. https://www.rkikuojohnson.com