Highest flying piston multi engine aircraft while carrying a 1,000 kg. payload (47,910 ft.): B-29
Highest flying piston single engine aircraft (56,046 ft.): Ca.161
Highest flying float plane (44,429 ft.): Ca.161 Idro
Highest flying cargo aircraft with 88,200 lb. payload (43,830 ft.): C-17
Highest flying helicopter (40,820 ft.): SA-315 Lama
Highest flying turbine helicopter with 2,000 kg. payload (28,743 ft.): CH-54/S-64
Highest flying piston multi-engine drone (67,028 ft.): Condor
Highest flying single engine turboprop (53,574 ft.): Egrett
Highest flying jet fighter seaplane (54,800 ft.): F2Y
Highest flying zoom flight of a U.S. jet aircraft (103,389 ft.): F-104
Highest flying electric propeller aircraft (96,863 ft.): Helios
High flying absolute zoom flight of a manned jet aircraft (123,523.58 ft.): MiG-25
Highest flying four engine jet seaplane bomber (40,000 ft.): P6M
Highest flying manned balloon (127,851 ft.): Red Bull Stratos
Highest flying rocket plane while transporting two passengers (367,441 ft.): SpaceShipOne
Highest flying sustained horizontal flight (85,069 ft.): SR-71
Highest flying twin pusher prop (60,897 ft.): Strato 2C
Highest flying rocket plane taking off from the ground (79,452 ft.): Sud-Ouest Trident II
Highest flying single engine piloted aircraft (68,700 ft.): U-2
Highest flying manned aircraft (354,199 ft.): X-15
Highest flying unpowered glider (76,124 ft.) Perlan II
Highest flying drone aircraft (110,000 ft.): X-43A
Highest flying kite (16,009 ft.): 12 sq. meter DT delta
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You don’t have a category for highest flying multi-engine turboprop.
The Tupolev Tu-95 Service ceiling: 13,716 m (45,000 ft), assuming that this is
without a payload [bombs] & with a limited amount of fuel & the usual Russian / Soviet Exaggeration.
Something smaller & more efficient must have flown higher…