This could be quite a list. Some of these date back to the 1970s when I first started flying. A lot of these are right seat or back seat, but some I actually had the stick/yoke in my hand. Here goes...
Very first flight in a Boeing 707, after basic training, Feb 1967, San Antonio to St. Louis.
PT-22, T-6D, T-6G, Harvard Mk II, T-28, T-34
PT-17, PT-19, BT-13, Tiger Moth
P-51D "Color Me Gone", P-51D "Ge Ge"
B-25J "Chapter 11", B-25J "Killer B", B-25J "Pacific Prowler", B-29A "FiFi"
Grumman TBM, S-2 Tracker, C-47 "Tico Belle"
Island Airlines Ford Tri-Motor, EAA Ford Tri-Motor, JU-52 "Iron Annie"
Piper Super Cub, J-3 Cub, PA-11 Cub, Piper Tomahawk, Aeronca Champ
Piper Comanche and Twin Comanche, Piper Aerostar, Piper Cherokee
Cessna 150, 152, 172, 172 Straight Tail, 185 on floats, 206, 210,
O-2/Skymaster, L-19/O-1
RLU-1 Breezy, Vans RV-8
King Air, V-Tail Bonanza, Fuji LM-1, New Standard D-25, Rockwell Twin Aero Commander
Schweizer 2-33A, Grob 2-Seat Sailplane
Sikorsky H-34, Jet Ranger, Bell 47