- Drunken pal of Prince Hal: FALSTAFF
- ____ on the Tracks, someone's fifteenth studio album: BLOOD
- Michael of Threat Level: Midnight: SCARN
- OR: The name of this city has come to mean "kidnap" or, in Australian English, "slingshot": SHANGHAI
- Abandoned, miserable, lonesome, wretched: FORLORN
- Quality distinguished by pedants from "precision": ACCURACY
- Infamous party boy Worthington: COREY
- OR: Creepy place, full of graves and skeletons: CEMETERY
- Olympian cupbearer: HEBE
The GIF of Wario is from the original Mario Party for the Nintendo 64, and his flavor text is trying to point you at the "Mario's Rainbow Castle" board. This is the only board in the game that has a distinct start and finish, instead of going around in a loop. But it does have branching paths! So you can fill in the answers above in order like this:
The letters on the red spaces and Bowser spaces (the "worst places" Wario mentions) spell out the answer, FAILURE. Which N64-era Mario(?) game says "Failure!" in a high-pitched voice if you mess up? I remember this very strongly, but I can't figure out where it's from.