First off, stand-up comedy is the HARDEST thing in the world. Professional comics spend decades honing their craft. That being said, nothing about Kellyanne Conway strikes me as funny! Unless it's Kate Mckinnon impersonating her on SNL, but you be the judge.
The cringeworthy footage is from when President Donald Trump’s advisor was running The Polling Company and competed in a “Funniest Celebrity in Washington D.C.” charity contest in 1998.