John Oliver famously predicted that Meghan Markle’s rendezvous with royalty wouldn’t be easy, and last night he told Jimmy Fallon how he knew three years ago what the rest of the world found out via Oprah.

“I didn’t find any of it surprising,” said Oliver, the host of HBO’s Last Week Tonight, during an appearance on NBC’s Tonight Show. “That was kind of what I felt, sadly, her experience was going to be going in because, you know, I grew up, I know the royal family from a distance and they seemed like flawed people.” Oliver added, “That’s literally the kindest way I can possibly put it.”

A three-year-old video clip in which Oliver said Markle was marrying into “an emotionally stunted group of fundamentally flawed people doing a very silly pseudo job” resurfaced with Markle’s revelatory March 7 interview with Winfrey. “It’s...