In the last half of the 1960s, US flights regularly wound up in Havana.
Yep. That's when the first "string" of airline hijackings took place. Despite the horror of what it's like to be on the business end of a pistol, most of them ended up fairly peacefully. They almost seem like benign hijackings by today's terrorist standards. Sometimes just a poor sap that wanted to get home.
Late night monologues and various comedy skits would often poke fun at these hijackings. "Take this train to Havana!" That sort of thing.
The Legend of D.B. Cooper - Has anyone heard of him before?
Wow. This question just shows my old age, I guess. In my aged mind this is like asking "Has anyone heard of Richard Nixon before?"

I mean...to an old fart like me it's sorta like "Well, who
hasn't heard of D.B. Cooper?"
You could not have lived back then and missed it. It was the O.J. or Scott Petersen or Martha Stewart or Enron story of it's time. Big news when it happened. And very quickly developed into both real and urban legend! Books, mini-series, movies...the works. Probably a theme park or bungee-jump ride out there somewhere named after him.