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The 5 Most Painful Moments From Kellyanne Conway’s Newly-Discovered Stand-Up Comedy Video

The horrifically awkward stand-up routine the Trump administration really doesn't want you to see

In case you’ve spent the past few days wondering what could be more trying, bleak, or empty than America’s current political climate, we’ve got some good news.

You can stop looking.

The answer lies in this recently circulated video featuring eleven minutes of stand-up comedy from Trump campaign manager-turned-adviser Kellyanne Conway. Indulge if you’d like, but plenty of the content is addressed below, so you don’t have to do this to yourself if you don’t want to.

It’s not worse than you think it’s going to be, but it’s almost certainly as bad as you expect. It appears that she’s doing her own material, which is fine, and it’s an old enough video (November of 1998) that it seems far enough removed from today that it verges on quaint, but…’s bad.

That said, it’s not worse than a million other bad stand-up acts. However, anyone who has experienced bad stand-up knows that it’s one of the most difficult and awkward things a person can endure. So parlay that sensation with the hindsight that the video’s subject is now the smiling face of Donald Trump’s White House. That would put it shoulder-to-shoulder with a Richard Spencer-led flash mob in the hierarchy of fun.

Rather than continue to speak generally about this video’s badness, let’s get specific. These eleven minutes offer a litany of cringeworthy moments, so let’s whittle it down to a modest five.

Awful Moment #5 – A Political Humor-Themed Cabaret Number

Can politics be sexy? Maybe. But political humor can never be sexy. However, late in the video, Kellyanne Conway steadfastly refuses to take “never be sexy” as an approach to a cabaret number as she wiggles and writhes her way around hamfisted references to Newt Gingrich and his ilk. Conway’s a former pageant contestant, so I suppose the musical finale was an inevitability, but it didn’t have to be this bad.

Does she sing the line “I’ve got the pundit blues?”


It would appear that God left Washington prior to 1998.

Awful Moment #4 – Her Broken Leg

Though it’s out of frame for most of the video, Conway performs her act while nursing a broken leg. She uses her ailment as a go-to gag periodically throughout the act. That’s right. She’s using her literal broken leg as a figurative crutch. That’s some Oscar Wilde-level shit right there.

If a performer’s up there in a skirt or dress with a cast on her leg, she needs to acknowledge it, but Conway (performing prior to her marriage using her maiden name Fitzgerald) really makes a meal out of it.

Not only does she use the cast on her leg for the “break a leg” bit you can see coming in slow motion from miles away, but she also makes it the subject of a Lettermanesque top-five list about how the injury occurred. This had some promise. But the promise dies quickly, as the second entry is a quip explaining the injury occurred because Chris Matthews needed another foot to put into his mouth and he only has two.

Awful Moment #3 – It Was For A Good Cause

Ok, this isn’t a moment per se, but it certainly warrants mentioning. Kellyanne Conway did this act as part of a fundraiser for the Child Welfare League of America. I’m not above saying that it would be easier to hate-watch this if it was for something extremely partisan or antagonistic, but the foundation’s stated purpose is to aid “children and youth who may have experienced abuse, neglect, family disruption, or a range of other factors that jeopardize their safety, permanence, or well-being.”

That’s difficult to indict. If she went up there to make an ass out of herself and tell corny Washington jokes to raise money for kids who need help, let’s give credit where credit is due.

Awful Moment #2 – “Pundette”

This video hails from 1998, so Conway’s political pandering consists largely of forgotten footnotes 19 years later. For instance, she refers to herself as a “pundette.” It’s like being a pundit, but you’re also a woman. The confluence of those two qualities apparently requires a sassier, more marketable word label than “pundit,” so we got the wildly unncessarry feminine suffix attached to it.

Thankfully forgotten, “pundette” was tossed around in political cirlces back then, a term trying paradoxically to convey both novelty and legitimacy in one dumb little word.When this act was performed, the term almost exclusively referred to conservative women appearing regularly on TV to discuss the Bill Clinton scandal.

If you can get past the inherently self-deprecating nature of the label, Conways does offer a somewhat funny job description for a pundette as “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.”

(Again, this is a bit more charming if you firmly plant yourself in 1998 and aren’t reminded of her place in the world in 2017.)

Awful Moment #2 – The Custody Battle Joke

In case you get drawn in by Conway’s siren call of polling sample jokes and shout-outs to think tanks, she offers a parable that will slam you upside the head with her true nature. Musing about her pro bono work in a recent custody battle involving abused children, Conway reveals that the judge ultimately sent the kids to live with the Washington Redskins because “they don’t beat anybody.”

Aside from the distasteful nature of the joke’s premise, we’re left wondering where the creative license for the joke begins. Was her pro bono work an invention for the sake of the joke? What about the case itself? Or was it just the judge’s exhausting punchline?

We might very well spend the rest of Kellyanne Conway’s career wondering where the performance ends and the person begins. Sadly, this weird video won’t bring us any closer to the answer.

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