Currently have 41 types without sub classes as in 747 100/ 200 etc. First ever flight was a Britannia (1967) and I managed one of the Air Toulouse Caravelles just before they were withdrawn. Slightly off the wall ones were an NAMC YS11 in Trinidad and an Aero Commander on a scheduled service substituting for a broken Twin Otter from Barbados to Palm Island.
Love to have flown more prop types so I guess DC6, Vanguard, Viscount. Recently added a C152 as I have just started PPL.