Today, we know Kellyanne Conway as the grinning, lifeless hack sent onto TV shows to drastically reconfigure the truth in the wake of her boss’s negligence. (Her official title for this is “counselor to the president”—fancy!) However, back in the late ’90s, she was known as Kellyanne Fitzpatrick, and at some point in that era she did an 11-minute stand-up comedy set that climaxed in a sexy jazz number. Does that sound awful? It is more awful than you can imagine.
Her jokes—which seem, admirably, self-penned—consist of mostly inside-the-beltway stuff (Capital Style editor Bill Thomas gets served), groan-worthy Leno jokes (“New survey’s out—” one begins), and a whole lot of comments about her weight and her bad sex life. In particular, she focuses on the trials and tribulations of being a “pundette,” the then-in-vogue term for young female pundits like Conway, Ann Coulter, Laura Ingraham, Maureen Dowd, and others. While initially a bit sheepish, fumbling over her punchlines, she gets into a rhythm with the pundette stuff before launching into what appears to be an original composition entitled “The Pundette Blues,” a jazzy cabaret number featuring then-topical name-drops like Kosovo, Newt Gingrich, and Monica Lewinsky.
It is awful, awful, awful, and a brief glimpse into the hell that is a life on the fringes of Washington, cracking self-deprecating jokes at moderately attended functions to mildly tolerant pollsters. It is perhaps this exact joyless thirst for power—and an obsession with insulting TV news ratings—that brought her and Trump together. Watch it if you dare.