1) Lockheed L1011 - Hands down the coolest airplane ever produced
2) Boeing 757-200 - They are just a damn sexy airplane, whereas the -300 looks like an anorexic chick.
3) Douglas DC-3 - Although I was born way after they were used in commercial service, I still enjoy watching them fly regularly as Mosquito Control spraying aircraft out of my home airport. 60 years+ of service.
4) DeHavilland Comet - The overall design was almost a work of art. The engines as an integral part of the wing and the fuselage shape just make this plane stick out in my head.
5) McDonnell Douglas MD
-80 - Not one most people would choose, but I was trained in it while at Continental, so it now holds a special place in my heart.