The one that hooked me, even though it took years to get going again was Saturn through a cheap reflector back in the late 60's.
The GAE in '17 brings me to tears being I was able to share it with my youngest daughter and her son, my youngest grandson.
A first total eclipse for us all.
Thanks to you here on the SGL, I can add the Mercury transit and Luna occulting Mars.
Two not really actual astronomy, but science/space was witnessing Apollo 11 launch at the Cape.
The other is a memory that will forever be with me! I was quite casually watching the Space Shuttle Challenger lifting off in the distance through my telephoto lens, just to use up the last of the film on the roll. Just as I focused it manually, it exploded.
I think I took a dozen images, the last showing contrails from the debris falling.