As mere SLF may I offer you a few, with favourite pilots (the type you know will always find the only flat spot in 100 miles to put you down in an emergency - the myth all pax believe):
Ghana Airways,when still under BOAC supervision, DC3 flown by Peter Dorkenoo.
Aden Airways DC3, especially when landed downwind on dirt into a mountain side at somewhere like Dhala by John Gross.
Mustique Airways Islander, flown by Celia Alexander, speciality: landing at (unlit) base after nightfall, so that you'll not miss your dinner date (or hers).
For the rustic experience: Silver City Bristol Freighter car ferries - stuff your hankie in the window frame to block the draft and stop it rattling, but not even the SRN4 or Eurostar have beaten 20 minutes cross-channel.
And for a true shuttle experience, the Electras between Rio and Sao Paulo in the '80s (who operated them?)