Back in the year 2000, writer Dave Eggers struggled to find the right title for his first memoir. What collection of words could possibly communicate the emotional enormity of losing both of one’s parents to cancer and then having to perform as a sudden surrogate to one’s younger brother? Eggers eventually stumbled upon the appropriately melodramatic moniker. The name he chose, A Heartbreaking Work of Staggering Genius, was equal parts sarcastic and sincere. It also felt grandiose enough to describe Eggers’ own slice of the confusing, oft exhilarating human experience. Now, some 21 years later comedian, musician, writer, director, and all-around tortured entertainer Bo Burnham has stumbled upon a heartbreaking work of staggering genius of his own. Bo Burnham: Inside is much more humbly named than Eggers’ classic work but it’s every bit as heartbreaking and yes, staggering. Inside is the best thing that Burnham has pulled off so far in his relatively young yet impressive career. It also might end up as a definitive bit of Western popular art to come out from the pandemic era. Speaking of death, there’s quite a lot of it in Inside. Nary a moment goes by without Burnham idealizing either his own suicide or the encroaching end of the world. The 30-year-old comedian mentions wanting to put a bullet through his brain, wanting to commit suicide by age 40, and poking fun at the commodization of “don’t hurt yourself” corporate messaging. In one song, he even identifies the end of the world as being precisely seven years from now. But one occurrence of death in the special comes at a particularly unexpected moment. And it’s the moment that I’ve not been able to shake since watching it. Despite all of the heavy subject matter, Inside is technically a comedy special. It’s most overtly and classically Burnham-ian song comes early in the proceedings. “White Woman’s Instagram” is a satirical tune about all the shallow and clout-chasing images that pop up on basic white women’s Instagram accounts. The song covers pretty much what you’d expect: a bowl of oatmeal with blueberries arranged in a peace sign, latte foam art, tiny pumpkins, and some random quote from Lord of the Rings attributed to Martin Luther King. Midway through the song, however, the content takes a hard left turn to the stunningly real and heartbreakingly empathetic. The lens of Burnham’s camera, which had been arranged into a narrow frame to resemble that of a cell phone, widen back out into a real world format then Burnham sings in all sincerity: “A photo of her mom. The caption says ‘I can’t believe it. It’s been a decade since you’ve been gone. Momma I miss you. I miss sitting with you in the front yard. Still figuring out how to keep living without you. It’s gotten a little better but it’s still hard. Momma, I got a job I love and my own apartment. Momma, I’ve got a boyfriend and I’m crazy about him. Your little girl didn’t do too bad. Momma, I love you. Give a hug and kiss to dad.’” Burnham is not breaking the fourth wall here. By all indications, both of his parents are still alive, well, and supportive of him. An earlier song in the special details the comedian trying to have a Facetime call with them. Burnham is therefore still in character as a vapid white woman in the song. And yet, among all of inconsequential social media posturing to be made fun of is one unexpected moment of real heartbreak. It’s Inside’s most remarkable moment of human kindness and empathy. Burnham has a complicated relationship with his audience, and seemingly with the rest of humanity at large. Tall, lanky, and with a confrontational stage persona, he’s always been a popular target for hecklers. In the standout closing number from his 2016 special Make Happy, he tells the audience “a part of me loves you, a part of me hates you, a part of me needs you, a part of me fears you.” By the end of this special, Burnham emerges from “Inside” looking like a scraggly Howard Hughes. An unseen audience rapturously cheers his arrival and he immediately tries to get back inside like a frightened animal. The comic also has an equally fraught relationship with technology and social media. The consummate millennial, Burnham began his songwriting and comedy career on YouTube and then got to watch as the social media space became something far more corporate and sinister. This special alone includes songs that feature Burnham criticizing Jeff Bezos and adopting the persona of the Internet’s carnival barker promising “a little bit of everything all of the time.” “White Woman’s Instagram” is then a byproduct of the two things Burnham fears the most: technology and other people. That’s why that one sincere moment tucked into it is so poignant. As someone who came up performing on the Internet, Burnham understands that most Instagram posts are performances themselves. But just like his own performances, sometimes something sincere…something real sneaks itself through. While Burnham has a sophisticated artistic vocabulary to occasionally express himself through, the vast majority of his peers merely have personal totems and some kind, honest words. In the case of this woman, all she has is a nice photo of her mom and the stark, unvarnished truth: I miss you.