My top 3 & the reason I think their weird:

1: Hawker Siddeley Trident; somehow manages to balance with an off centre nose gear, has 4 wheels per main landing gear giving them a weird design of rotating forwards while retraction & rotating backwards while deploying.

2: B-36 Bomber; just search it up & see for yourself…

3: Boeing B-52; the landing gears on the belly retract & deploy sideways, can’t they just retract & deploy forwards & backwards?