Difficult choices, it was a pleasure to read the entries and I apologize to the worthy entrants not mentioned here...
Contenders:
mattrom @31: close to winning but the required GK is a bit arcane.
fieryjack @12, patrich @ 35: Anything lampooning the 45th POTUS deserves high praise IMO.
Medalists:
Bronze - buddy @3 : I was intrigued by this self-referential paradox and couldn't have worded it better.
Silver - paul @13 with his dim punter, second by a narrow margin. Kudos and partial credit to tyke51 for admirable sportsmanship.
Gold - peterm @ 27 with
"Old maid tucks into chopped mint, not sage (9)". Practically a coin-flip vs. paul @13, I give peterm the nod due to the clever association of "sage" and "mint".
Congratulations to peterm! Enjoy the prizes. The clips are overly long, and perhaps the second is simply weird, but there are entertaining passages.
The Saint, season 3, episode 10:
https://www.youtube.com/watch?v=FHlQCHbCbBE
Imprudent Iron Phoenix, vintage kung fu film:
https://www.youtube.com/watch?v=AL16QuPjLc8