We Talked to Two Philly Comedians About Kellyanne Conway’s Stand-Up

Kellyanne Conway is an advisor to the most powerful person in the world, President Donald Trump. The South Jersey native was originally a Ted Cruz supporter, but joined the Trump campaign and became the campaign manager in August. She led the campaign to an upset victory over Hillary Clinton in November, and is now a White House counselor. She became famous last week when she called Donald Trump’s lies “alternative facts.”

And back in 1998, she told a child abuse joke at a child welfare benefit.

The above comedy routine, performed by Conway at the 1998 Washington’s Funniest Celebrity contest, first surfaced on C-Span’s website and has been aggregated around the Internet. I figured such a powerful woman’s stand-up set needed some professional analysis. So I forced two comedians to watch it: Longtime local funnyman Chip Chantry and Blake Wexler, a Philly native who has worked with Todd Glass and on Key & Peele.

But first, Conway’s joke.

“Very few people know that I still practice law,” says Conway, who was Kellyanne Fitzpatrick before she was married. “I had a case in D.C. recently. It would have broken your hearts. It certainly broke mine. It was a custody battle. Vicious divorce, horrible custody battle. Little Becky and Little Tommy, and the judge says, ‘You’re old enough, kids. Becky, who do you want to live with?’ And she says, ‘Please don’t make us live with mommy, because she beats us.’ And the judge says, ‘Okay, Tommy, who do you want to live with.’ He says, ‘Your honor,’ holding back tears and holding on to his little sister Becky, ‘we can’t live with daddy because daddy beats us.’ The judge says, ‘Done! Go and live with the Redskins because they don’t beat anybody.”

Just as Conway — who immediately says she’s an Eagles fan, in a season where the team went 3-13 — is telling her child abuse/football joke, the camera zooms out to reveal the organization benefitting from this comedy event: the Child Welfare League of America.

“I’m sure anyone could seem relatively normal for a couple of minutes, but the longer you’re up there, the more of a chance we see who you really are,” Wexler says. “She literally made a joke about abused children just for a football punchline. You know, you could made a joke about football without bringing up abused children in a blasé manner … You could have talked about two restaurants you didn’t like and have the same punchline, but she went with one of the saddest things you could bring up.”

Chantry also laughed at her choice of jokes about blond “pundettes” (women who talk on cable news, which was apparently a portmanteau people used in the late ’90s): “Those are offensive jokes from like second grade about starving people — that’s all it is. I heard that and knew it was offensive in second grade.”

Conway also ends her routine with a song, about the trials and tribulations of being a “pundette” on cable news. (This stand-up bit was so long ago that not only does Conway joke about MSNBC’s low viewership, but she jokes about FOX News having low ratings.) “The song went on for days,” Chantry says. “My favorite part was when she wasn’t singing.”

Both Wexler and Chantry say they wouldn’t normally be so hard on a first-time stand-up comic. But since she’s become a mouthpiece for the much-hated president, they were happy to critique her performance. Would stand-up comics watch her set and laugh at her in the future?

“She told alternative jokes,” Chantry said. “I could see Donald Trump picking her after seeing her sing that song. It’s long and painful to watch, but I took a lot of enjoyment taking in that pain.”

Wexler had a different take: “I actually hated every second of it, and I hope no one watches it.”

There’s one more interesting thing about Conway’s set. Washington’s Funniest Celebrity has been around since 1994. But it frequently raised little to no money for the children’s charities it pledged to support. In 2009, the man who organized the event blamed the charities for not doing enough legwork to make money. In 2014, it ditched the pretense and dropped the charity aspect.

In summary: Kellyanne Conway did a stand-up bit at an event with a track record of giving little to know money to charity. Sounds like something her current boss would do, honestly. Now that’s the start of a pretty good joke — it just needs a little work.