Michelle Wolf, the comedian known for her sharp political satire and stand-up routines, continues to build her career following her 2018 roast of then-President Donald Trump at the White House Correspondents’ Dinner. Wolf’s set drew significant attention, particularly a joke about White House Press Secretary Sarah Huckabee Sanders burning facts to make eyeshadow, which sparked considerable controversy. Reflecting on the backlash, Wolf said she would now aim to be even more pointed in her commentary, especially given the administration's ongoing actions.

Wolf’s rise in comedy began after a brief and ill-timed career in finance. She arrived in New York in the summer of 2007 to work at Bear Stearns just weeks after two of its hedge funds collapsed. She describes her time there as joining “a sinking ship” but denies any responsibility for the 2008 financial crisis. The crisis indirectly motivated her to pursue comedy full-time after attending a taping of Saturday Night Live with friends in 2008. Inspired by the performers’ improv backgrounds, she took classes while still working in finance, slowly shifting to part-time jobs before leaving the industry entirely.

Wolf’s comedy repertoire includes writing for Late Night with Seth Meyers, collaborating with comedians like Hannibal Buress and Chris Rock, and joining The Daily Show with Trevor Noah in 2016. Her stand-up shows, including her HBO special Nice Lady and Netflix special The Well, often tackle challenging topics such as racial prejudice, sexual assault, abortion, and gender roles, with a style that targets all genders equally. Even since becoming a mother, Wolf maintains a provocative approach, rejecting the notion that parenthood should temper her material.

Now based between Barcelona and London due to family considerations, Wolf cites improved healthcare, food quality, and especially safer schools as reasons for relocating to Europe. She highlighted the absence of school shooting drills as a particularly important factor, acknowledging that such comments may elicit criticism from some in the U.S. political right. Nevertheless, she continues to emphasize that her comedy holds both political sides accountable and dismisses criticisms of cancel culture, arguing that while people can be upset by what comedians say, the freedom to express controversial opinions remains intact.

Wolf has also voiced concern over the growing clout of some U.S. comedians and podcast hosts, particularly those who platformed Trump before his presidency. She criticized the irresponsibility of spreading potentially unverified information to large audiences and the failure to challenge offensive behavior, especially on shows hosted by figures like Joe Rogan. While Wolf appeared on Rogan’s podcast in 2019, she now regards it as part of a broader problem with misogyny and a lack of accountability in certain comedy circles.

Discussing her views on the relationship between comedians and political power, Wolf expressed discomfort with stand-ups who align too closely with presidents or political figures, regardless of party affiliation. She prefers comedy that critiques power structures from an independent standpoint, citing George Carlin as a model.

Despite the mixed reactions to her 2018 White House performance—including Trump publicly calling her a “filthy” comedian and this year’s Correspondents’ Dinner being disrupted by a gunman—Wolf has not ruled out returning to the event. She stated that she would be open to another invitation, provided there is clarity about the nature of her act, and remains active with a current UK tour and a planned U.S. tour in November.