In his third comedy special, Ramy Youssef isn’t afraid to go to dark places. Over the course of the hour-long “In Love,” Youssef defends people who appeared in pictures with Jeffrey Epstein, complains about being the only comedian not invited to the controversial Riyadh Comedy Festival and grills his audience about their fears of AI. Yet these complex topics never feel too bleak. That’s because Youssef can make discourse about even the most upsetting subjects feel like a cathartic chat with a funny best friend.

“I do sincerely believe that we’re all in it together,” he said. “I know that can sound campy, but that actually is the glue for me. The reality is we’re all thinking about those things, and we’re all experiencing a version of them. That’s why it almost feels like I have to go dark, and I have to talk about religion, money and pedophiles, because we do need the ability to push through some of that stuff.

“It’s like there’s an elephant in the room,” he added, “and maybe we can make the elephant fart.”

More than any special Youssef has released before, “In Love” proves why he’s one of comedy’s most distinct voices. He started working on it shortly after 2024’s “More Feelings.” Though the comedian notes that “In Love” is likely his most “punchline heavy” special, it transcends the typical stand-up show, evolving into a conversation between Youssef and his audience.

“In Love’s” shooting style allowed for such intimacy. Filmed at Chicago’s Hideout theater in front of an audience of roughly 100 people, the special has a cozy quality to it. “It was kind of an inverse. It was my biggest tour but then the smallest venue,” Youssef said.

He wanted the setting to feel a bit like the final scene of Martin Scorsese’s “Raging Bull,” where Robert De Niro’s Jake LaMotta — after falling from fame as a boxing champion — performs stand-up in a small club. “I always thought that was such a great portrait of what it looks like trying jokes out in front of a small crowd,” Youssef said.

That closeness is emphasized by “The Bear” creator Christopher Storer’s direction, which favors intense close-ups of Youssef’s face as he works through his feelings about complicated issues, as well as audience asides that can be half-heard — like someone asking him the name of his dog in the middle of a segment about the possibility of his pet being a #MeToo villain. Storer shot the routine on film rather than digitally, a decision that added to the scratchy authenticity of the hour and ramped up the adrenaline of the performance for Youssef. “There were a couple of tightrope things I loved because they made it feel even more like a live performance,” he said.

Most of “In Love’s” intimacy comes from Youssef himself. As the title suggests, he does share several sweet stories and jokes about his wife, whom he married in 2022. But as the hour unfolds, it becomes clear that the love Youssef is referring to isn’t just for her. It’s for his audience as well as comedy itself.

“When I first started doing stand-up, I definitely had a bunch of (classic) punchline jokes,” he said. “At a certain point I started to feel like ‘Anyone could tell this joke’ or ‘This could be a killer tweet, but why am I up here? What’s the
point of the interaction?’”

Those questions led Youssef to lean into his more sincere style. “In Love” is full of difficult exchanges with the audience, from how much people paid for their weddings to their thoughts on job security and their purpose in life. Time and time again, Youssef shows he’s not just willing but eager to go to these thorny places with a crowd, a fellowship his audience mirrors through their honest revelations.

“I want to keep pushing this format. I want to keep pushing myself,” he said. “I
want to enjoy this and find as much nuance as possible in it.”

This story first ran in the Comedy Series issue of TheWrap’s awards magazine. Read more from the issue here.