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Watch Kellyanne Conway’s Awkward 1998 Stand-Up Routine

Top Trump adviser bumbles through bits about punditry in unearthed clip from charity event

Long before she was one of Donald Trump‘s top spin masters, Kellyanne Conway was a burgeoning pollster and pundit – and, as a recently unearthed video shows, a one-time fumbling stand-up comedian. In a video first posted by a user to C-SPAN, Conway (then Kellyanne Fitzpatrick) delivers a cringeworthy 11-minute set packed with a special brand of dad humor for deeply embedded Washington insiders.

The clip is dated November 26th, 1998 and Conway’s set is part of an event called, “D.C.’s Funniest Celebrity Charity Event.” Conway, apparently in a cast, opens with a few “break a leg” jokes, including a “Top Five” list for how her injury occurred: “Number four: Having just two of his own, Chris Matthews needed someone else’s foot to stick in his mouth.”

Later, Conway goes on an extended bit about being a “pundette,” a term coined at the time to describe young female pundits like herself, Ann Coulter, Laura Ingraham and Maureen Dowd, per the A.V. Club. In what’s possibly her most Nineties joke in a set filled with them , Conway quips: “What’s the one difference between a pundette and Ally McBeal? Ally McBeal‘s on a major network.”

At the end of her set, Conway grabs a feather boa and makes a handful of passing remarks about the investigation into Bill Clinton’s affair with Monica Lewinsky before launching into her grand finale: An original a cappella lounge song with the clunky hook, “I’ve got the pundit blues.”

In This Article: Donald Trump

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