In 1998, she was trying her hand at comedy while working as a pollster and footage of her performing at a Washington charity event has recently emerged.
One of the jokes would later echo her stardom.
"A pundit is someone who goes on TV constantly and just says the same thing over and over and over and over again, but never wears the same outfit twice," she says in the video.
In another awkward moment, she said: "Lead story now is Saddam Hussein, and I don't know nothing about that! But they'll still invite me to chat. As long as I'm blonde and not too fat!"
The footage comes as Conway attacked the Today show Wednesday for reporting that first daughter Tiffany Trump is registered to vote in New York and Pennsylvania.
Conway dismissed it as a false report, saying, "I talked last night to Tiffany Trump, and she said it is flatly false that she is registered in two states."
However, a Philadelphia County elections office confirmed to NBC that Trump's youngest daughter is registered to vote there, while public records in New York City show she is also registered in the Big Apple.