The silly prop has some serious comedy history. The pickle was given to Fallon by previous “Late Night” host Conan O'Brien in 2009. O’Brien received the pickle from David Letterman‘s staff in 1993. Before that, the giant plastic pickle was a staple decoration in the Letterman offices.
A few days before Fallon’s first “Late Night” (which was on Mar. 2, 2009), the charming comedian shared the pickle’s tale — and a sweet letter — from his predecessor in an online video.
“Whenever you’re done — which won’t be for a long time — make sure you pass it on to the next sap,” O’Brien penned and Fallon read aloud. “Knock ‘em dead.”
Fallon opined at the time: “It just kind of put everything in perspective, even though I’m holding a giant pickle …What a great tradition this is and what a great honor that I’m following in the footsteps of these great comedians.”
Below is another photo of the ceremonious moment. Watch Fallon discussing the tradition in 2009 beneath that: