As the United States Supreme Court’s nine justices convened to wrestle with a question of exceptional constitutional gravity—whether former President Donald Trump had overstepped the boundaries of executive authority by unilaterally imposing broad tariffs on nearly every trading partner across the globe—a different kind of observer sat quietly in the gallery. Among the rows of lawyers, clerks, and journalists, comedian and actor John Mulaney listened attentively from the back of the courtroom. Most widely recognized for his stand‑up performances, his stint as a talk show host, and his voice role in the animated feature ‘Chip ’n Dale: Rescue Rangers,’ Mulaney was not merely a curious celebrity visiting the nation’s highest court. His presence carried a distinctly personal and intellectual purpose.
According to Akhil Reed Amar—a highly acclaimed Constitutional law scholar, Yale Law School professor, and a close mutual friend of both Mulaney and attorney Neal Katyal—the comedian’s attendance at the oral arguments that Wednesday was prompted by both friendship and genuine academic fascination. Katyal, a renowned litigator, partner at Milbank LLP, and former Acting U.S. Solicitor General, was at center stage presenting arguments on behalf of two coalitions of companies challenging the legality of Trump’s tariffs. These tariffs were enacted through the International Emergency Economic Powers Act (IEEPA), a statute ordinarily utilized to address national security emergencies rather than economic trade disputes. Amar explained to Business Insider that Mulaney, though best known for his wit and timing, possesses a deep and abiding interest in the workings of American government. “My friend John is far more than a world‑class performer,” Amar remarked. “He is, in truth, a thoughtful public intellectual who takes a serious interest in constitutional law and civic life. So it comes as no surprise that he would wish to witness firsthand one of the most consequential Supreme Court debates in recent memory—particularly since his close friend Neal Katyal was the focal advocate of the day.”
After the proceedings concluded, Mulaney infused a bit of characteristic humor into the moment by sharing on X, formerly Twitter, a courtroom illustration drawn by C‑SPAN’s communications director, Howard Mortman. With understated comedy, Mulaney captioned it, “Cheap seats but a great show.” The post underscored his knack for finding levity even in august institutions. Earlier that year, Katyal had revealed during the Aspen Ideas Festival that he and Mulaney were collaborating on an upcoming television project—a drama‑comedy centering on the Supreme Court itself. Katyal described it as a series reminiscent of ‘The West Wing,’ aiming to illuminate judicial decision‑making through storytelling. “I’m writing it with John Mulaney,” he said, noting that their shared ambition is to harness popular media and the performing arts to provoke meaningful public reflection on the concept of justice. Whether the duo continued their discussion about the series after the day’s session remains undisclosed; neither Katyal nor Mulaney’s representatives provided comment to Business Insider regarding that possibility.
Mulaney’s enthusiasm for the law is hardly spontaneous—it is, in fact, a legacy. His parents, Ellen and Charles Mulaney, are both accomplished attorneys who graduated from Yale Law School. Ellen served for years as a professor at Northwestern University’s law school, while Charles built a distinguished career as a corporate attorney at the prestigious firm Skadden Arps. Their shared professional background created an environment in which dinner‑table conversations often revolved around judicial theories and legal precedents, nurturing Mulaney’s lifelong curiosity about the legal system.
Wednesday’s Supreme Court event marked at least the second occasion when Mulaney shared a room with a sitting justice. Earlier in 2024, during a Yale Law School reunion, Justice Sonia Sotomayor sat in the audience as Mulaney moderated a session titled “Conversation on Textualist Approaches of Constitutional Interpretation,” featuring both Amar and Katyal. It was during this sphere of interdisciplinary dialogue—where legal scholarship intersected with intellectual curiosity—that Mulaney’s engagement deepened. Amar has recounted that his friendship with Mulaney began when Ellen Mulaney encouraged her son to listen to Amar’s podcast, ‘America’s Constitution.’ Fascinated, John devoured all 250 episodes, later inviting Amar to Chicago for a live discussion celebrating his mother’s birthday. Amar smilingly recalled that Mulaney “nerded out about law” during the event, hosting his mother’s friends for an animated conversation about constitutional principles—a testament to how genuinely and earnestly he approaches subjects few comedians ever explore.
The admiration between the two men evolved into creative collaboration. Earlier this year, Mulaney lent his distinctive voice to the audiobook version of Amar’s work ‘Born Equal,’ bringing the dense legal prose to life for a broader audience. On the eve of the Supreme Court hearing, Mulaney even reached out to Amar seeking a copy of an amicus brief authored by Amar’s brother, Professor Vikram Amar of the University of California, Davis. That brief, which analyzed how presidential powers rarely revert to Congress once extended, became directly relevant to the very issues debated before the Court. “John is a serious guy,” Akhil Amar emphasized. “He genuinely wants to read the briefs.”
The overlapping worlds of Mulaney and Katyal are not confined to the courtroom or academic symposiums—they spill into the realm of entertainment as well. In May, Katyal appeared on Mulaney’s Netflix show ‘Everybody’s Live with John Mulaney,’ where the two shared an unconventional discussion on property law and squatting. With characteristic humor, Katyal quipped that landlords are “a sorry bunch” for being “the only people outside of England who call themselves lords.” The tables turned the previous year when Mulaney joined Katyal’s legal podcast ‘Courtside,’ engaging in a sophisticated yet humorous conversation about the challenges faced by prosecutors investigating presidents. Katyal affectionately referred to Mulaney as a ‘Constitutional law nerd,’ crediting him as one of the inspirations for launching the podcast. “He’s constantly texting me thoughtful questions about obscure Supreme Court cases,” Katyal revealed. “And they’re genuinely good ones.”
Although Mulaney remained silent during Wednesday’s arguments, the hearing itself was punctuated by moments of levity that drew laughter in the courtroom—a rarity in such solemn proceedings. According to the official Supreme Court transcript, the justices and audience laughed eleven times. One particularly intellectual jest came from Justice Samuel Alito, who teased Katyal for invoking the nondelegation doctrine—a principle asserting that executive agencies cannot wield powers not specifically granted by Congress. With gentle irony, Alito remarked, “I never imagined you’d become known as the man who revived the nondelegation argument,” referring to Katyal’s prior role in defending broad agency powers during the Obama administration. The courtroom responded with chuckles, revealing that even serious constitutional debates leave room for humor.
Another moment of comic tension emerged when Oregon Solicitor General Benjamin Gutman, arguing for twelve states opposed to the tariffs, sparred verbally with Justice Brett Kavanaugh. Kavanaugh observed that Gutman’s logic contained “a doughnut hole,” questioning his distinction between the president’s authority to impose embargoes under IEEPA and his inability to levy taxes. Gutman swiftly countered, suggesting that while tariffs might resemble embargoes superficially, the two instruments were fundamentally distinct because taxes raise revenue for the government. “It’s not a doughnut hole—it’s a different kind of pastry,” Gutman quipped, provoking laughter throughout the room. Kavanaugh conceded with amusement, replying, “That’s a good one.”
What began as merely another day in the nation’s highest court consequently transformed into a convergence of law, intellect, and comedy. For John Mulaney, it represented not just an act of friendship but also a reaffirmation of his deep respect for the American legal tradition—one that continues to fascinate him as both a citizen and a storyteller. From courtroom benches to the creative halls of television production, he and Neal Katyal exemplify how the boundaries between disciplines can blur, and how humor and jurisprudence can coexist—revealing that even amid the gravitas of constitutional debate, there is room for curiosity, collaboration, and the occasional well‑timed laugh.
Sourse: https://www.businessinsider.com/john-mulaney-supreme-court-tariff-argument-supporting-lawyer-neal-katyal-2025-11
