Leo Calvin Rosten was a Polish-born American author, teacher and researcher. He is branded as a comedian in the sphere of screenwriting, stories, journalism and lexicography of Yiddish, a standard German language of Ashkenazi Jewish origin. He was a language connoisseur who familiarized Americans with terms and expressions of a different lingo. He brought into light the distinctive Jewish culture, their concepts and beliefs through his work in Yiddish; and how it has augmented the present day English. Through his writings, he reflected the nuance world of meanings profoundly buried within a tale, joke, idiom or other modulations related to it. His writings never failed to reveal his humoristic approach. He was a voracious reader with a broad array of intellect. He is best-known for his stories about the night school ‘prodigy’ Hyman Kaplan, written under the pseudonym Leonard Q. Ross and his encyclopedic ‘The joys of Yiddish’, is full of Jewish anecdotes and humor. His witty style of writing is quite apparent in critically acclaimed ’Hyman Kaplan’ which has been compared to the comic characters of Dickens and Shakespeare by the critics. It is one of the most-read classic works of American humor.