Randomly watched a Freebirds in the WWF match from the Spectrum, where they get the big babyface rock star entrance with Cyndi Lauper and David Wolff seconding them. And I'm well aware of this as a big idea of Vince's around the time, but it still just seems so WEIRD that it happened, in the manner that it did.
Anything comes to mind as being similarly out of place, even though you're well aware of it happening?
(And not Russo insanity like Heel Canadian Jim Duggan. Too easy.)
Robocop the character acting as a legit second for Sting in 1990.
Honky Tonk Man in WCW.