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When The Daily Show's Michelle Wolf hosts the White House Correspondents’ Association Dinner on April 28, she will become only the fifth woman to do so.
The annual dinner, put on by White House journalists, was not always a welcoming space for women. Although the event has existed since 1921, only in 1962 did female journalists gain the right to attend — in large part through the efforts of reporting legend Helen Thomas, who pushed President Kennedy to pressure the event organizers into changing their rules.
Wolf, who in December put out her HBO comedy special Michelle Wolf: Nice Lady, will be following the work of her Daily Show colleague Hasan Minhaj, who hosted last year. For the second year in a row, President Trump has elected not to attend the event — a break from past presidents. In an interview with The Hollywood Reporter, Wolf seemed unfazed. “He's terrible,” she said, “because you can't joke a joke."
In honor of Wolf’s hosting gig, we are highlighting the four trailblazing female comedians who have hosted the dinner before her.
In the same year that then-President Barack Obama introduced his Anger Translator, played by Key and Peele’s Keegan-Michael Key, Saturday Night Live star Cecily Strong led the night with scathing critiques of the media, including CNN. "Whenever a big story breaks, I can turn to CNN and watch Anthony Bourdain eat a cricket," she said. She also skewed C-SPAN, which aired the event: "Tonight’s event is being broadcast on C-SPAN. So, to some viewers watching at home on C-SPAN, hello. But to most viewers watching at home on C-SPAN, 'Meow.'"
Strong, who is now well-known for her Melania Trump impression, hosted the dinner just months before Donald Trump announced his surprise presidential bid. Among recent news events were protests that erupted in response to the death of 25-year-old African-American Baltimore resident Freddie Gray at the hands of local police. Strong didn’t shy away from the issue, quipping, “Let’s give it up for Secret Service. I don’t want to be too hard on those guys. They’re the only law-enforcement agency in the country that will get in trouble if a black man gets shot.”
In the first White House Correspondents Dinner following the inauguration of President Barack Obama, Wanda Sykes ignited controversy for her pointed jokes about the President’s critics. In response to conservative radio host Rush Limbaugh’s public hopes that Barack Obama would fail as president, Sykes said, “That’s treason. That’s not saying anything different from what Osama bin Laden is saying. … I think maybe Rush Limbaugh was the 20th hijacker but he was so strung out on Oxycontin he missed his flight.”
Sykes, an Emmy-winning writer for The Chris Rock Show who also starred in the Julia Louis-Dreyfus-led The New Adventures of Old Christine, had similar criticism for Sean Hannity. After noting that Hannity had offered to be waterboarded for charity, Sykes said, “ He can’t take a waterboarding. I can break Sean Hannity just by giving him a middle seat in coach.”
Elayne Boosler had already become one of the first women to received her own one-hour comedy special, which aired in 1986 as Party of One, when the White House Correspondents’ Association chose her to headline the dinner. Bill Clinton had just been elected president, and Boosler, a regular on political comedy shows like Politically Incorrect, had harsh words for his predecessor George H.W. Bush. On Bush’s lack of support for an automatic weapons ban, which Bush claimed could infringe on the rights of hunters, Boosler said, “I think if you need a hundred rounds to kill a deer, maybe hunting isn’t your sport.”
In a 2015 interview with Elle, Boosler remembered her time hosting the dinner — and the importance of comedy in trying political times — like this: “The worse something is, the more the public needs to see it through the [lens of] humor — to make it more understandable, less intimidating, less apocalyptic. Everything horrible demands comedy, and nothing is more horrible than the U.S. Congress these days."
At the tail end of the George H.W. Bush presidency, Paula Poundstone became the first woman to host the dinner, nine years after the tradition of comedian performances began in 1983. Poundstone, who first came to prominence through a series of stand-up specials on HBO and through her political commentary on The Tonight Show With Jay Leno, trailblazed a path for politically minded women comics.
Yet despite Poundstone’s many digs during the dinner, when she woke up the next morning, news reports focused on her choice of clothing — a white tuxedo — rather than the content of her remarks. “I think that might have been the one time that I ever thought about the fact that I was a woman,” she said to Elle. “Because would they have done that for any other performer?”
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