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Wolf was employed at Bear Stearns from 2007 to 2008, later at JPMorgan Chase, working for almost four years in mutual funds and managing accounts between the two banks. Around the time of the buyout by JPMorgan, Wolf started improv classes at the Upright Citizens Brigade and the Peoples Improv Theater (PIT). Her frustration with the imperfect and ephemeral nature of improv and the encouragement from classmates got her to audit a stand-up class at the PIT. Her first appearance on late-night television was in July 2014, when she went on Late Night with Seth Meyers. She re-appeared on numerous segments on Late Night, often as her fictional persona, "Grown-Up Annie", an adult version of Little Orphan Annie. She later held additional positions on the same show, including, most recently, as writing supervisor.
Wolf delivered a 19-minute comedy routine and was both praised and criticized for her "harsh and stinging" jokes aimed at the Trump administration--most notably at Sanders--and at the media itself. Wolf's criticism of journalism was called by one commentator "the most consequential monologue so far of the Donald Trump era." The management of C-SPAN radio considered the monologue so risqué that they stopped broadcasting it half-way through, worrying that she might violate FCC indecency guidelines and that they might get fined. Wolf's joke about Sanders using the ashes of lies to create her perfect eye makeup became the most controversial issue among the criticisms aimed at Wolf's presentation:
I actually really like Sarah. I think she's very resourceful. She burns facts, and then she uses that ash to create a perfect smoky eye. Like maybe she's born with it, maybe it's lies.[a] It's probably lies.
Journalists including Maggie Haberman of The New York Times,Mika Brzezinski of MSNBC, and Andrea Mitchell of NBC News, criticized Wolf on Twitter for targeting Sanders. Ed Henry of Fox News stated that "[i]t was disgusting, despicable."CBS News executives reportedly considered ending its participation in future dinners, but later changed its stance after the network was assured that the Correspondents' Association would "seriously consider changes to the dinner's format." Former press secretary Sean Spicer tweeted, "Tonight's #WHCD was a disgrace" to which Wolf replied, "Thank you!" The next day, Trump called several outside advisors to criticize the comedian, and he sent a series of tweets saying that the "so-called comedian" and the "filthy 'comedian' totally bombed." and called for the dinner to be discontinued or "start[ed] over."
Wolf questioned her critics from the media: "Why are you guys making this about Sarah's looks? I said she burns facts and uses the ash to create a *perfect* smoky eye. I complimented her eye makeup and her ingenuity of materials." In an interview with Terry Gross on NPR, Wolf said that the joke was not about Sanders' looks at all, it was about her lies, and there is not really a need to defend it in the first place. She said she did not attack any of the women's physical appearances unlike some male politicians such as Mitch McConnell's neck or Chris Christie's weight, but "as a woman, I have access to hit women in a way that men might not be able to hit them with jokes." Talking about her performance, "I wouldn't change a single word that I said. I'm very happy with what I said, and I'm glad I stuck to my guns."
Other journalists, including Jacob Soboroff of NBC News, Joan Walsh of CNN, Amanda Hess of The New York Times, and Wesley Lowery of The Washington Post, tweeted their support for Wolf and took the White House Correspondents' Association (WHCA) to task for the statement issued by its president, Margaret Talev. Talev wrote that the program "was meant to offer a unifying message about [the WHCA's] common commitment to a vigorous and free press while honoring civility, great reporting and scholarship winners, not to divide people," and that Wolf's "monologue was not in the spirit of that mission."James Poniewozik, writing for The New York Times, criticized the WHCA for disavowing Wolf, saying that she was "defending the mission of the White House press: sticking up for the truth. Michelle Wolf had the WHCA's back Saturday night, even if it didn't have hers the day after."The New Yorker's Masha Gessen was particularly impressed with Wolf's criticism of journalism, praising her for how she "exposed the obscenity of the fictions" of "The Age of Trump".
Wolf hosted a weekly Netflix talk show, The Break with Michelle Wolf, which premiered May 27, 2018 and was discontinued on August 18, 2018. Before the show premiered, it was announced that it would "take a break from the seriousness of late-night comedy" and "instead of making the news fun, she'll make fun of everything and everybody. There will be no preaching or political agenda--unless it's funny." She was also an executive producer for the show. Netflix released the trailer to coincide with her appearance at 2018 White House Correspondents' Dinner. Netflix ordered a 10-episode season that premiered in May 2018 and aired over 10 weeks, with the series finale on July 29, 2018. The show was cancelled after one season, having not drawn enough of a viewership to secure a renewal.
In December 2019, Netflix released Joke Show, a stand-up comedy special written and performed by Wolf.
^Parallels a Maybelline slogan, "Maybe she's born with it. Maybe it's Maybelline."