This is a comedy skit for a roast of Rudy Giuliani from 2000, when Giuliani was the mayor of New York, and Donald Trump’s multi-casino bankruptcy, failed mortgage business, failed travel business, and failed steak business were still a few years in the future.
To borrow a line from Business Insider: “The skit was good for a few laughs at the turn of the 20th century. But now it reappears routinely to baffle the internet as the lives of its two protagonists take stranger and stranger turns.”