riddle me this/that
- a catchphrase used to introduce a joke, observation, question, or riddle.
- making a demand of a listener to note a situation about to be mentioned or a question, mostly ones that are hard to explain or solve.
- posing a challenge to a person to answer a question with no apparent answer.
- used to sarcastically or humorously pay emphasis to a question, undercutting the self-assuredness of another person.
- a rhetorical way of questioning conventional wisdom.
- pointing to hypocrisy or a contradiction or creating wry observations.
- Despite acting so confidently, riddle me this: how will we get all that money within a day?
- How will you pay for all your plans if you quit your job? Riddle me that.
- Riddle me this: why was such a talented collective so horrible in their work?
Riddle me is an idiom whose use can be traced back to 1615. People use it as a way of presenting a brainteaser. A notable early use dates from 1693, when the English author John Dryden uses it in his translation of an ancient Roman satire, where the speaker says, “Riddle me this, and guess him if you can, who bears a nation in a single man.” The phrase appears in another play acted in 1700 when a character in it uses it as an introduction to a puzzle. The American Folklore Society, in 1924, has it that in Jamaica, the phrase occurred in a chant used before riddles; “riddle me this, riddle me that, and perhaps not.” It established itself by the middle of the 1900s when a Broadway musical was staged in 1933 under the title Riddle Me This. A riddle book was also published in 1940 under the title Riddle Me This.
However, its popularity rose in the 1960s when The Riddler, a villain in the Batman TV series, played by Frank Gorshin, used to preface the riddles he intended to use in taunting Batman, including Riddle me this. In Batman Forever, Jim Carey, the actor, also used the phrases “riddle me this” and “riddle me that.”