Before Donald Trump’s first State of the Union address, late-night hosts were all sharpening their tools, with plans for live broadcasts and stellar booking feats—like Jimmy Kimmel securing Stormy Daniels, the porn star with whom the president allegedly had an affair in 2006. But making hay of Trump’s actual words proved difficult—particularly for those who focused their energies on his speech, an ominous performance that was nevertheless less bombastic than the usual Trump fare.

This set the stage for a surprising turn of events: Kimmel—a host known, until recently, for being largely apolitical—wound up with the most fascinating episode of the night, thanks to a pair of segments that were both baffling and profoundly uncomfortable. As Trump’s time in office wears on, late night’s comedians have increasingly fallen in line around one approach. Most hosts use their monologues to critique the president and his administration, riffing on the news of the day from various angles. Seth Meyers, Stephen Colbert, and Trevor Noah dig into policy; although Kimmel doesn’t shy away from those discussions, he typically resists the urge to dive too deep on any one subject. But Trump’s speech on Tuesday night was, shall we say, more “low energy” than some might have expected—leaving hosts who took the usual approach without any truly punchy lines or Twitter memes to play with. Kimmel, on the other hand, ended up with something unique; following a speech in which the president painted illegal immigrants as criminals and insisted, “Americans are dreamers, too,” the comedian’s decision to highlight the DACA debate with a pretaped segment proved both timely and difficult to watch.

Kimmel has increasingly found his niche in the shifting late-night landscape as the genre’s everyman. He paints himself as a guy who doesn’t understand policy minutiae, but seeks to learn more—and whose moral center is pronounced enough for him to call out craven policies when he sees them. Usually, when Kimmel does get political, he focuses on issues that affect him directly: he waded into the health-care debate after his son was born with a congenital heart defect, and he delivered a stirring monologue about gun control following the mass shooting in his hometown, Las Vegas, last year.

On Tuesday night, however, Kimmel made an even bolder move by airing a segment in which he sat down die-hard, DACA-opposing conservatives across from a family that relies on DACA. Unlike, say, a bit in which Kimmel impishly tricked Trump supporters into embracing Obamacare, this one was decidedly serious, and unusually raw. Late-night hosts have brought together panels to discuss such issues before, but facilitating a debate between both sides—especially on a subject this sensitive—is rare. The effort didn’t feel cynical in the way that, say, using human-rights debates to sell beer does—but it was undeniably awkward and, in the end, achieved little reconciliation between the two sides.

Kimmel himself resisted falling into easy platitudes, even when doing so would have helped him smooth over the tension. After some argument, one of the conservatives told Kimmel, “We can agree to disagree, but I know that you will concur with me that we live in the most loving, compassionate, and exceptional country.” He did not agree: “I think this country has become cruel,” Kimmel said, gesturing toward the DACA recipients. “Look at this woman and her husband who’s in the military. Where is your compassion?”

By the end, the comedian proclaimed—unsurprisingly—that he had “made almost no progress” toward inspiring empathy in the conservative group. But it was a fascinating step in Kimmel’s journey toward finding a new way to present political material—and it was just one portion of an episode that was shockingly experimental, especially for a program that is now more than 10 years old. Throughout, Kimmel flitted from a monologue focused on Trump’s State of the Union address, to the uncomfortable DACA segment, to a pretty standard interview with Kerry Washington, to a completely bonkers Stormy Daniels interview that somehow didn’t end up being most biting, uncomfortable portion of the evening. (Daniels’s sit-down was complicated by a statement purportedly from Daniels that surfaced just hours ahead of the broadcast, in which the porn star allegedly denied her reported affair with Trump; she spent her time with Kimmel dodging questions and playing coy, refusing to give straight answers one way or another, most likely to avoid violating a non-disclosure agreement.) The hour was sometimes frustrating, but it was never predictable.

Yes, the Stormy Daniels interview ended up as something of a wash; while Kimmel’s struggle to get her to say anything concrete was played for laughs, the sit-down was borderline infuriating for those who already worry about the amount of false information circulating in our national discourse. Still, their interview was undeniably fascinating television—a feat that’s increasingly hard to pull off as late night becomes ever more crowded. And as Kimmel continues to hone his brand within late night’s political landscape, this installment will be an important one to remember—for better and for worse.