Comedian Volodymyr Zelenskyy vs the then president of Ukraine Petro Poroshenko.

From Wiki: "In place of traditional campaign rallies, [Zelenskyy] conducted stand-up comedy routines across Ukraine with his production company Kvartal 95."

So I guess that counts...

Zelenskyy v Putin?

Only in cartoons.

I mean, there was that time Roy Hattersley was supposed to be on HIGNFY and he didn't turn up, so they replaced him with a tub of lard on the basis that it was "liable to give much the same performance and imbued with many of the same qualities".

Not as deranged as what's going on in the USA right now, but it was fucking funny.

Chaplin and Hitler come to mind, but I think a big difference is politicians traditionally believe they are above petty spats with comedians. Trump, being the giant narcissist bitch he is, can't help himself but engage.

Lenny (1974) https://www.imdb.com/title/tt0071746/

Had a hard time believing it was a true story.

https://en.wikipedia.org/wiki/Lenny_Bruce

Bassem Youssef and Egyptian President Mohamed Morsi?

https://en.wikipedia.org/wiki/Bassem_Youssef

“Leader”? No.