I knew a guy, who upgraded from LHS of an ATR-72 directly to LHS of a 777. Now, this idea gives me wet dreams!
Ha! That's nothing!
Many people know/knew a guy who went from RHS is a very aristocratic sounding UK airline to Chief Training Captain (yes, it's true!) of a very smarmy sounding one.
He didn't last long, but he sacred the crap outa lotta folks in the meantime.