I have to cop out and do two lists... off ice and on ice moments.
I think we're looking for fairly objective moments here, not favorites. A top 5 moment can't be that time you took a girl to a game and she got so excited by a shirtless Rob Ray that she became amorous in the postgame show.
Off ice:
No particular order.
Rick's banner night... Rigas perp walk... Spin of the Wheel... Pegula Presser... Closing the Aud
Would have included the decision to tank but that probably wasn't a discrete moment.
HM: Landing Bowman?