It is supposed to be difficult making new friends after 30. This is a truism so agreed upon that the New York Times regularly runs the same article about it, wistfully reminiscing about the halcyon days of a youth passed by. But that’s not always the case, especially for guys like Austin (Paul Rudd), that affable dude with the cool-new-kid hair and a rockin’ ‘satche that inexplicably matches the one Rudd sported in Anchorman. This delightful creation in Andrew DeYong’s venom-laced comedy, Friendship, leans heavily on Rudd’s famed charm and eternal youthfulness. Not only is Austin made to deliberately echo Brian Fantana and the general good vibes of 2000s, Judd Apatow-produced bromances like I Love You Man (which Rudd also starred in, albeit as the square), but the movie likewise trades on a preternaturally boyish charm. Whether you squint or stare, you’ll see in Austin that chill guy who could always hang and forever win over new pals, be it in elementary, middle, or high school. Or for that matter middle age. Yet Friendship is not Austin’s movie; it’s Craig’s (Tim Robinson), a put-upon schlub so desperate for approval that his very countenance conjures another boyhood staple: the lonely nerd whose otherwise sympathetic isolation somehow becomes exhausting. And then, eventually, infuriating. Writer-director DeYoung’s script carefully crafts a house of cards around Craig’s life that back in the I Love You Man and Ron Burgundy days could have held together long enough to duct tape on a Hollywood happy ending. Therein lies the real black-hearted brilliance of the piece though. This isn’t a love letter to bromances, or a contrived lament about the lonely male epidemic; it’s a cruel, nihilistic, and positively delightful indictment of the fragility that fuels both our fantasies and failures. And the tragedy of Craig is that he’s got a front row seat to see how this cycle continues, if he would only ever look around and stop whining. The first act of Friendship certainly puts you in the poor bastard’s shoes. In the first scene during a group-help session for cancer patients, Craig’s wife Tami (Kate Mara) reveals she’s been in remission for months. She also says she hasn’t had an orgasm in twice as long. Craig swallows his embarrassment and pride in the same breath, just as he does in the next sequence when Tami and their teenage son (Jack Dylan Grazer) ignore Craig as he pleads for one of them to see “the new Marvel” with him. Fine, want to go to dinner with dad? Do anything!? Yet his wife and child are literally framed as practical lovers, with the son kissing his mom goodbye for the night, while Craig sits alone in a recliner abandoned in a wide frame. It might as well be a desert island. In this context, Craig falling for Rudd’s dreamy smile and nonchalant demeanor after Austin and his wife move in next door makes sense. It’s even sweet as Austin leads Craig on an adventure through the local sewer like this is the fun half of a Stephen King book about kids and clowns. Later he invites the neighbor to see his cover band with the bros. Through it all, DeYoung suffuses the film with the tension of a punchline withheld. The slow boil awkwardness of Robinson’s overeager smile begs for the shoe to drop—for the bad thing to happen. It might therefore take most of the film for some to realize Craig is the bad thing. And like a bomb, it’s only a matter of time before he consumes everyone near him in a cringe comedy inferno. The appeal of this approach is that Friendship takes on the gait and suspense of a New Hollywood tragedy while slowly extracting its laughs ever at Craig’s expense. In another’s hands, this might have really been a eulogy about the loss of connection in the age of technology. But right down to the revelation of Craig’s career as an app designer who’s responsible for making smartphone programs more addictive, the emphasis is Craig is the author of his own lifelong cosmic joke. Mara’s Tami is clearly drowning Craig out, but dropped lines about off-screen subplots involving her high school ex clue us into the fact Craig is even less engaged in the lives of his family. Everything from his subjective point-of-view is confirmation that he’s taken for granted and neglected; a victim befitting his age. But if he represents any kind of damaged masculinity, it is of the fragile, deluded variety that in a different time would have worn a mohawk and followed Harvey Keitel down a dark alley. Today, it’s a wonder he isn’t whining on X about there being a Latina Snow White. Robinson’s macabre pity-party grows only louder as the indignities pile up and we finally enter the outright surreal. In its most successful moments, the film even achieves a fairytale dreaminess. It’s almost a happily ever after as we watch this schmuck torch friendships, a marriage, and a career all while in constant search for why no one cares. The answers he discovers, particularly after going on a mind-altering drug trip to discover his inner-truth, marks the hardest I’ve laughed at a movie theater in at least a year. Join our mailing list Get the best of Den of Geek delivered right to your inbox! Friendship is in theaters on May 9. Learn more about Den of Geek’s review process and why you can trust our recommendations here.