I've brought this up before, but it's worth a re-mention after you said this.
Leo Hulsman tried breaking his wife, Dora Hall into "the biz" in a strikingly similar way. The difference?
Leo Hulsman being the owner of the SOLO cup company meant he had a lot of money. He also diversified somewhat by owning real estate in the form of a few recording studios and sound stages. He also had rapports with some actors and singers as YUGE BIDNESS owners could handily afford to rub elbows with movers and shakers.
So one thing he did was allow Dora to LARP Dean Martin and Flip Wilson by recording cringey variety shows and then try getting them syndicated.
Once Upon a Tour was one such example I spoke about before. Hulsman bribed the likes of Oliver, Rich Little, Frank Sinatra Jr. and Rosie Grier to appear. They did, but holy shit... And you could just see with your own eyes the classic "Bitch, that check better fucking clear!" in their eyes and on their faces with each performance.
Still got nowhere with syndication. Still got nowhere in da bidness. Why? Because Dora Hall is so transcendingly bad, you will get hickeys from all the sucktitude. Just like the greasy gourd.
Check the first five minutes at least: Russell Greer quality shit "jokes" while not trusting the audience along with Russell Greer tier pest action.