The Simpsons mixes The Great Gatsby with hip-hop in misfiring special

The first attempted marriage between F Scott Fitzgerald’s heralded novel The Great Gatsby and hip-hop culture was Baz Luhrmann’s 2013 film adaptation starring Leonardo DiCaprio, a gaudy yet somehow hopelessly drab undertaking that (for whatever reason) sought to reimagine Jay Z’s Izzo as a flapper anthem, among other things. Last night’s episode of The Simpsons, The Great Phatsby, tried its hand at goofily bridging the same gap between the Roaring Twenties drama and a rap music video, subjects that only meet at their appreciation of excess, only this time it was supposed to work much better because at least they would be in on the joke.

The Simpsons has been around long enough to be referenced by three generations of rappers –from De La Soul to Lil Boosie to Kendrick Lamar – and over the course of its run it has even guest starred a few, too, most notably Cypress Hill, 50 Cent, and Ludacris. In the early 90s, Bart made a rap song for the album The Simpsons Sing the Blues and some years later, in the episode Pranksta Rap, he went to a rap show that turned into a rap battle on stage and won with multisyllabic schemes. An animatronic Abraham Lincoln raps and beat boxes at Duff Gardens in Selma’s Choice. Homer raps as Poochie when he briefly gets a job on the Itchy & Scratchy show in season eight. Each and every attempt to make use of the form as a joke medium or storytelling device has been astonishingly corny and surprisingly forced. Rap and The Simpsons have flirted for some time, but not once has the relationship actually borne any fruit.

This Great Phatsby wasn’t the exception, but rather a demonstration of the rule in motion: with an opportunity to do something daring they churned out something wholly and utterly banal.

The Mr. Burns-centric episode opens with the tycoon remembering his heyday as a young overindulgent party host throwing extravagant Jay Gatsby-like soirees where entire fortunes were lost at his craps tables. In an effort to relive his youth, he decides to replicate one of these gatherings, only this time on a penny-pincher’s budget. The resulting event is terrible, and so with hopes of cheering him up, Homer takes Burns to crash another fat cat’s mansion party.

After marveling at the festivities, they long to meet the host, and are introduced to a capitalist named Jay G. (a bit on the nose, no?) When he was a young hustler, Jay found a copy of Burns’ book, the Rungs of Ruthlessness, on a seat of “a bus he jacked”, which subsequently inspired him to become a rap mogul. He is delighted to meet Burns and decrees that the party is now being held in Burns’ honor. The festivities bring back the feeling Burns was trying to recapture early on.

The party is something straight out of a Luhrmann fantasy, just one where the event planner is Cookie from Fox’s Empire — equipped with waterfalls, hor d’oeuvres delivered on motorcycles, and guests free falling over colossal subwoofers. (Attendees include Beyoncé, Spike Lee, Flavor Flav, Cornel West, and Dennis Rodman.) The two billionaires strike up a friendship, and as Homer puts it, it’s an odd couple: “A man who signed Rick Ross and a man who dated Betsy Ross.”

The relationship sours when the Obsidian Card – a supposed Black Card on steroids – Jay G gives Burns turns him back into the reckless spender he was in his youth, and bankrupts him. After his things are repossessed, Burns learns, via the Jay G diss record Monte Burnt, that the rap mogul owned the Obsidian company all along and was out to ruin him. It’s mostly downhill from there, both for Burns and for the episode, which has a tough time getting any good Great Gatsby jokes off, or any good rap jokes off, and sometimes even getting their standard jokes off, too.

Mr Burns, with Homer and Bart as his only aids, hatches a revenge scheme and what unfolds for the next half hour is a shoddy composite of rap urban legends and origin stories: Dr Dre meets Suge Knight meets Sugar Hill Gang meets Empire season one (Taraji P Henson guest stars as a not-so-subtle Cookie knock off.) Most of it is nonsensical, and very little of it is funny.

Burns, who has teamed up with his new nemesis’ ex wife (played by Henson) and an old Jay G collaborator who wrote his early raps, orchestrates a diss track with RZA, Snoop Dogg, and Common as Hate Squad and the Rhyme Crime All-Stars. The jokes are predictable: RZA references Wu-Tang Clan, Snoop Dogg smokes weed, and Common promotes peace, positivity, and spirituality. The raps are all terrible; the traditional made-for-TV slock you get when producers and writers are trying to simulate what rap music does without actually making any.

In the end, no one hears Burns’ diss because Jay G arrives as a hologram at the show to announce that all of the track’s co-conspirators sold out for money. “Selling out” is just one of the many overworked ideas the episode draws from and that well dried up when rappers were drinking Cristal. The entire adventure, if it can be called that, is a jumble of rap cliches and stale tropes: the hologram bit, a nod to Tupac’s 2012 Coachella appearance during Snoop Dogg and Dr Dre’s headlining set, is the most novel of them. The only one-liner of the show that actually lands is one Bart lets slip in passing; when on the hunt for clues about Jay G’s past, he identifies the ultimate experts on rap music as white nerds. It’s subtle and sharp, something the rest of the episode is not.

The only sneaky good moments in the episode have almost nothing to do with the rap dramedy slothfully unfolding at its center. Other members of the Simpsons family learn more about decadence and superfluity in the margins than Burns or Homer do the rest of hour. The most effective subplot finds Lisa trapped in a romance with a pretentious rich kid and at odds with her own moral compass. His appraisal of her seems to create a sketch of an apathetic upper class: “I’ve never met anyone like you – anyone with, you know, morals.” When she demands that he change, he decides to fight for a cause she likes to win her back, only to see her give up on her morals when another suitor offers VIP access to an equestrian show. It’s the entire “selling out” bit with far less window-dressing but way more punch, underscoring the cause of this hourlong misfire: more often that not, less is more, and rap is more than just shiny things.