I watched 11 minutes of Kellyanne Conway doing standup. It took me 28 hours.

Kellyanne Conway was not a hit at standup comedy. We still wish we'd stuck with it.

Kellyanne Conway was not a hit at standup comedy. We still wish we'd stuck with it.

 [Editor’s note: This week, a previously forgotten video clip began circulating of Kellyanne Conway, a senior adviser to President Donald Trump, doing standup comedy in Washington, D.C. City Pages asked Twin Cities comedian Rana May to watch the clip and give us her professional and personal opinion of Conway’s work. It took a little while.]


From the description on Youtube, it appears this is from a charity event in 1998. I looked up the logo on the banner, and it’s for the Child Welfare League of America. Which means, at one point, Kellyanne Conway gave a shit.

0:11 – 0:30

Kellyanne holds the mic very close to her face, as if someone might take it away. She self consciously makes an inside joke about being quoted accurately by a man who may be named “Ralph Hello.” The crowd seems to understand. They laugh. It sounds like the crowd is mostly men. Men who aren’t afraid to laugh.

0:30 – 0:35

Kellyanne Conway, previously Kellyanne Fiztpatrick, back when she cared about children, reveals that her leg is in a cast. She makes a joke about breaking her leg in both the literal and figurative sense. She then injects a non-sequitur that she believes is a sequitur: “And you think blondes are dumb.” Conway is blonde, but it’s still impossible to tell why she said this. The important thing is, she came very close to saying, “You think dumbs are blonde.” This is the only part I laughed at.

At this point I took a little break to fill out a job application and send out another resumé, because I not only need a job, but a job with healthcare, before the Trump administration rescinds protection for people with pre-existing conditions. I stupidly got an MRI the last day on my old insurance, and found out I have arthritis.

0:35 – 0:45

Kellyanne pauses to check her notes. I get it.

0:45 - 01:20

Kellyanne makes a shocking revelation that she has a “congenital deformity,” i.e. birth defect. I also have what my mom used to call “a congenital hip." This made me feel close to her for 10 seconds... until I hoped that she would experience a set of circumstances that led to her paying hundreds of extra dollars per month to get health insurance to cover completely random anomalies that were present at birth.

Suddenly I couldn’t take anymore. I put on my sweater coat and some lipstick and went to meet some friends. I think everyone knows the experience of watching comedy is optimized with the right amount of alcohol intake. I had three drinks and then went to a bar close to my house, where I saw an old friend whose name rhymes with my name. We used to date the same guy and he would mix our names up. That was in 1998, when Conway’s standup video was made. That guy is still a shithead and so is Kellyanne Conway.


Kellyanne launches into a list of five “real” reasons why she has a cast on her foot. She’s really milking this goddamn cast thing. Again it’s all inside jokes, and bragging about who she rubs shoulders with. (“Having just two of his own, Chris Matthews needed another foot to stick in his mouth.”)

People who try standup for the first time often write way too many jokes about doing comedy. Everyone forgives their narcissistic meta jokes because it’s their first time. But none of those people went on to become the Counselor to the President and invent the term "alternative fact."

And then in a vanilla-as-fuck move, she makes fun of Fred Thompson (R.I.P.) and his alleged “bizarre and kinky foot fetish.” She was likely just making a joke, and he never had a foot fetish. But if he did, it’s still the most widely known and accepted fetish. It’s not like he peed on her. Which also is totally fine, and I’m not gonna kink shame here. Everyone should pee on someone they love.

Also did I mention she invented the term “alternative fact” live on TV last weekend?

For some reason, I am reminded this video was made before 9/11.

At this point I stopped paying attention. I made some coffee and thought about how someone had just asked me to do an unpaid charity show. Just like Kellyanne Conway! The difference is she was a lawyer who owned a polling firm, and decided she’d be great at standup comedy, whereas I am a comedian.

It’s hard to tell what kind of circumstances led up to this hot mess of a standup set, but I have to think it was the widespread belief that doing comedy is easy, mixed with Conway’s colleagues' excitement at watching her fail.


It appears that this is some sort of comedy contest, and she is now attempting to roast the other comedians. I would love to know who won. She makes fun of Bill Ginsburg, former lawyer for Monica Lewinsky; Bill Thomas, editor of a Washington, D.C. magazine that stopped printing in 2000; and Norm Orenstein, which Conway says sounds like the name of a baby. (This leads me to believe she has never met a baby.) Some of these people she’s roasting are dead. They’ll be joined soon by thousands of Americans who can’t afford to have cancer.

3:10- 4:10

She makes a joke about a “pundette” being a “lightweight lightweight.” I really don’t understand it. Is she saying men are fat? I have no idea. And that is ok because not all comedy is for everybody. This comedy is for the people in the room -- people who I wish would have stopped her from the horrors she is inflicting on them, then, and me now.

Then she makes some street jokes, substituting “pundette” for blonde. Street jokes are just regular jokes with a set-up and punchline that people tell each other casually. “Why did the chicken…?” or, “A guy walks into a bar…” or, in Kellyanne’s case: “How many pundettes can you fit in a shower? I don’t know, they keep slipping down the drain.” I suppose someone, somewhere, makes up these jokes. But she didn’t. In regular standup, this is frowned upon by comedians. But whatever. You’re supposed to cheat at a charity contest, right?

Like 6:00 until whatever

I have a little hangover but it was worth it. Kellyanne says people don’t like lawyer jokes, then proceeds to do a lawyer joke about child abuse at an event where the backdrop says “Protect America’s Children.”

7:51ish I think

“I do politics.”

What does this mean?

8:00 - 8:39

She comes up with some slogans for upcoming campaigns. They don’t make any sense. Maybe it’s history. Maybe it’s her. It’s probably her.

9:00 until the end of this goddamn horror show

This is bizarre. She puts on a red boa and does an a cappella song in a New York-maybe-Italian-maybe-Bronx-type accent. The song is called “Pundette Blues.” This makes sense because of course the history of the blues is deeply intertwined with New York Italians. It’s really long, and it’s full of clever little rhymes like, “Kosovo now tops the news/only guy in my life is Chris Matthews.” And: “Lead story now is Saddam Hussein/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.” It’s important to note here that nobody is laughing.

Something bizarre and quite awful happens to people when they try comedy for the first time. They get addicted, immediately, and after investing all of fifteen minutes decide to spend years pursuing this thing they only tried once in their life.

It ruins people’s lives. If I had a time machine, I would go back to 1998 and find Kellyanne Conway on this night, in this room, and catch her by the wrist just as she was hobbling off stage on her non-cast leg.

“Kellyanne,” I’d say, “didn’t it feel good to have the respect of your peers? Wasn’t that great? You’re never going to believe me, but I’m from the future -- by the way, heads-up, a few of these guys are not long for this earth -- and I came here to say you have a very bright future in standup comedy. What I need you to do is walk out of here tonight and become a comedian. Quit doing politics. Sell your house, move to LA and start going to open mics. Trust me, Kellyanne. If you do that, everything is going to be so much better.”

Watch Conway's ... "comedy" performance below.