Slang dictionary
riddle me this
[rid-l mee this]
What does riddle me this mean?
Riddle me this is a stock phrase used to introduce a riddle, joke, observation, or question.
Where does riddle me this come from?

TheÌýphrase riddle me this appears as early as 1615 to present a small brainteaser. One notable early use comes in 1693 fromÌýEnglish author John Dryden’s translation of an ancient Roman satire. In it, a speaker says, “Riddle me this, and guess him if you can, Who bears a nation in a single man?” (The Greeks, for what it’s worth.)
In an English play from 1700, a character again uses the riddle me this construction to introduce a puzzle:Ìý“Riddle me this, then. What’s that goes round the house and round the house and never touches the house?” The speaker is joking about how he led a group in circles rather than heading straight home.
In 1924, the American Folklore Society recorded that “riddle me this, riddle me that, guess me this riddle and perhaps not” was used in Jamaica as a formulaic chant before riddles. By the mid-1900s, riddle me this was well established as a familiar stock phrase.ÌýA Broadway musical,ÌýRiddle Me This, was staged in 1933. A book of popular riddles was published underÌýRiddle Me ThisÌýin 1940.
In the 1960s Batman TV series, the villain The Riddler, played by Frank Gorshin, often prefaced riddles he would use to taunt Batman with the phraseÌýriddle me this.ÌýIn 1966, Gorshin released a novelty song in character reciting a number or riddles prefaced by his catchphrase.ÌýActor Jim Carey memorably used “Riddle me this, riddle me that” when playing the villain inÌýJoel Schumacher’s 1995 Batman Forever. Gorshin and Carey helped cement the phrase Riddle me this, Batman in the popular lexicon.ÌýFor example, a 2009 Adweek article used the phrase to open an article considering whether a writers’ strike led to a proliferation of reality TV shows or vice versa.
Examples of riddle me this
Who uses riddle me this?
In colloquial speech and writing, riddle me this is sometimes used rhetorically to question conventional wisdom, point to a perceived contradiction or hypocrisy, or make wry observations. An article in the railway trade journalÌýThe Signalman’s Journal, for example, used the phrase in questioning why government subsidies are readily accepted for airlines and trucking companies but not passenger rail service.
Riddle me this, Batman can be used in any of the contexts, owing to the phrase’s association with the Riddler. A 2011 book of philosophical essays related to Batman was titled Riddle Me This, Batman. Also, thanks and allusion to Batman’s Riddler, riddle me this is often paired with riddle me that for further expressive effect.
Note
This is not meant to be a formal definition of riddle me this like most terms we define on Dictionary.com, but is rather an informal word summary that hopefully touches upon the key aspects of the meaning and usage of riddle me this that will help our users expand their word mastery.