It takes a special kind of writer to successfully merge comedy and tragedy. In many instances, you need to make your audience feel bad for you, but you also have to grant them permission to laugh. Fusing pity, sympathy, humor, and glee into a woozy concoction of pathos is not a simple feat to pull off, but there’s a reason tragicomedy is such a potent mode of expression, one that Shakespeare favored. You invite everyone to gaze at your pain, put themselves in your shoes, and imagine going through the exact same misfortunes that have befallen you. It’s an act that calls upon both commiseration and voyeurism, a means of gesturing toward your circumstances and saying “can you believe this shit?” Some things are so ridiculous and unreal that stifling your laughter in the face of them feels like a herculean task. One of the best tragicomic writers we have right now is Open Mike Eagle. Across the rapper’s increasingly vast discography, he has dug through himself and the world around him for microscopic scrutiny, displaying them in all their hilarity and misery. On last year’s “my co-worker clark kent’s secret black box,” Eagle rapped from the perspective of someone who worked in an office with Superman-in-disguise: “This is some bullshit / I don’t know why y’all be trying to act like / Y’all don’t know who that is / This is fucked up.” 2020’s similarly superhero-themed “Sweatpants Spiderman” chronicled life as a fresh divorcé who starts “studying Kendrick” and “dressing like Hendrix” to avoid becoming washed. For DOOMED!, his first full-length collaboration with innovative producer Kenny Segal, he burrows further into heartbreak, framing it through a classically comedic lens complemented by Segal’s instrumental maze of delirium. It’s a perfect pairing, one that augments Eagle’s farcical melodramas-in-miniature through Segal’s percussive, occasionally jazzy sense of foreboding. Early on, “DOOMED!” makes a compelling case for both Eagle’s sharp pen and whimsical improvisations. He explores the multidimensional nature of heartbreak and how it manifests in all types of relationships. Romance is not an exclusive domain of disappointment; he breaks up with his therapist (she would repeat herself but was unaware of it), his barber (they ghosted him), and his primary care physician (he was on his ex’s insurance). Nearing the song’s end, he seemingly runs out of people to break up with, so he redirects his aim at insentient concepts, like all the anime shows he’s bailed on and the now-ineffective whale songs he once used to lull him into slumber. Once you think he’s aired all his grievances, he rattles a bunch more off the cuff before Segal’s beat fades out and takes him with it. He describes break-ups, his own lyrics, and watching various new movies by himself as “ass,” “shit,” “fucked up,” and, perhaps most scathingly, “not fun.” Underneath it all, Segal’s piano- and sax-heavy instrumental takes on a kaleidoscopic effect, as if Eagle is gazing through its refractions, his periphery surrounded by a bevy of bygone memories and regrets. Hemlock Ernst, AKA Future Islands’ Samuel T. Herring, joins for a gutting guest verse on “Unfinished Concrete Initials,” in which a wedding-planning session turns into an engagement-ending argument. The gravity of the scenario finds its most devastating symbol in a couch, which Ernst selects for its versatility: it fits his whole body, it’s good for hosting parties, and it’s a decent writing station and meditation spot. Meanwhile, Segal’s melancholic choir samples and lethargic drums drive home the all-consuming loneliness that rests at the song’s heart. Opening track “Out to Lunch,” which Segal adorns with sonar-like synths and uneasy woodwinds, captures Eagle’s wit and woe. He delivers the cutting line “my body’s a house that I haunt” over drums that knock with equal weight, only to cheekily apologize for “putting my sadness on main” mere moments later. As a frequent denizen of the internet, Eagle has a penchant for injecting online humor into the sorrows of real life. It’s a tactic that would dilute the message in less capable hands, but he possesses the charisma and cleverness that make it super effective. Eagle’s wordplay is impressively inventive and phonetically satisfying. He opens “The Many Hustles of My Lonely Time Traveling Uncle” with the tongue-twisting “I used to sell CDRs and VCRs and bet money on DDR in seedy bars.” On “Schrödinger’s Green Room (There but Uninvited),” he raps over booming bass and boisterous brass about eschewing enigma, instead opting for something more direct and authentic to himself. “I ain’t mysterious,” he raps. “Neither hardcore nor fake serious / I make what I make, period.” For “Infinity War Spoilers,” Segal’s plinking vibraphones and pinging ride cymbals echo the nausea of its narrator, in which Eagle repurposes Peter Parker’s famous “Mr. Stark…” scene (the song’s name told you!) to articulate his social anxieties. He keeps up the Marvel references for the final track, “Watching a Movie Called Freedom by Myself,” in which there “ain’t no post-credits scene” so “we can all just leave,” as a palpable wave of dejection—which Segal embellishes with tremolo-kissed Rhodes keys and muted snares—closes like a curtain. The moment lingers with the finality of irreparable heartbreak, and the whole thing admittedly feels a little bit ridiculous. At that point, all we can do is laugh. I mean, can you believe this shit? [Backwoodz Studioz] Grant Sharples is a writer, journalist, critic, and musician. His work has also appeared in Interview Magazine, Uproxx, Pitchfork, Stereogum, The Ringer, NME, and other publications. He lives in Kansas City. You can follow him everywhere @grantsharpies.