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Pop culture obsessives writing for the pop culture obsessed.

The Simpsons’ “super-sized rap Gatsby episode” is best in its low-key charms

Kevin Michael Richardson as Jay G (Screenshot: Fox)
Kevin Michael Richardson as Jay G (Screenshot: Fox)
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For all the hype about “The Great Phatsby” being The Simpsons’ first-ever hour-long episode, and the understandable skepticism about its description as “a rap-flavored parody of The Great Gatsby,” the episode’s origins are decidedly more modest. “This was just going to be a regular episode, but the table read went so well, in a fit of passion and excitement and ambition and excess, we decided to supersize it,” is how Simpsons executive producer Matt Selman puts it, and that makes sense when looking at the final product.

The story—Mr. Burns is befriended, then swindled, by a rap mogul—could be the synopsis of any old Simpsons episode, centering as it does on a side character and hanging as it does on a high-concept hook. The episode is even neatly halved (all the easier to syndicate with) at the 22-minute mark, when Homer (acting as the Nick Carraway-esque narrator) kicks off the rest of the episode by pronouncing, “F. Scott Fitzgerald once wrote there are no second acts in American lives. But he never said anything about second parts in American TV shows.” And each half of the super-sized episode even has an underbaked B-story of its own, as Lisa is wooed by a rich little jerk and Marge opens a darling and impractical boutique, both in Mr. Burns’ tony, West Egg-style summer residence of Middle Hampton.


That all being said, the episode’s charms are better than modest. If, as Selman says, ”The Great Phatsby” sort of mushroomed in the process, it’s understandable, as guest stars Kevin Michael Richardson (as Burns’ nemesis Jay G) and Keegan-Michael Key (as former Jay G musical collaborator Jazzy James) do stellar work in sizeable roles. Richardson has done multiple spots on the show in recent years and is such a versatile and comfortable presence on The Simpsons that he’s become something of an unofficial regular. And nobody has to sell Key at this point, as his ability to inhabit comic characters in short order is ideal for his role as the former rapper turned high-end candle salesman here. And with a brief but juicy role for Empire’s Taraji P. Henson (as Praline, Jay G’s very Cookie-like ex-wife who joins Mr. Burns revenge plan in the second half), and amusing cameos from real life rap royalty RZA, Common, and Snoop Dogg, there’s enough legitimate blackness to make the whole ”Simpsons do a rap episode” thing less cringe-inducing than perhaps the initial description made it sound.

Plus, the episode looks great. From Burns’ shadowy Xanadu-like mansion, to Jay G’s opulent Gastby-style gala (Jay G shouts out to Baz Luhrmann for design help), to the old-timey flashbacks of Burns’ party-throwing heyday (Babe Ruth swats a huge diamond into the night), to Burns poverty-stricken digs in the Burns family crypt, the styling of the episode is ambitious enough to give credence to those thinking there’ll be another Simpsons movie someday. Even though a Burns-centric theatrical film isn’t anyone’s first call, there’s enough emotional sweep to the Burns-Jay G relationship to make “The Great Phatsby” feel significant enough to carry one. The actors are the biggest reason, both Harry Shearer and Richardson throwing themselves fully into their characters, with Richardson’s sonorous gravitas and Shearer’s lived-in craftiness in finding Burns’ center matching up as equally formidable friends, then foes. When narrator Homer sums up their eventual rapprochement (both being mostly-evil billionaires after all), his words carry the improbable weight of significance, despite them both, as said, being really big jerks. Says Homer of Burns, “His ruthless will to power would beat on forever in another man’s heart.” Aww. Hey, wait.

(Photo: Fox)
(Photo: Fox)

Anyway, the longer running time leaves plenty of room for gags to breathe, something credited co-writers Selman and Dan Greaney take advantage of. Homer the slow-thinker is one of my favorite Simpsons comedy stylings, and the mid-episode gag where Homer narrates every extended, tortuous symptom of Burns’ agony at being swindled out of his fortune is just great. (“The loneliest moment in someone’s life is watching their whole world fall apart. And all they can do is stare blankly. Oh no—wait, he’s crying now. That’s worse… Oh, he tripped over a dog!”) Jay G’s house party (and the very “gay steel mill” vibe he brings to the nuclear plant once he takes that over) all contain enough inventive excess to keep the ee entertained—I especially liked the women being launched into the pool by strongmen hitting those carnival bell-ringers, and the people performing wind-tunnel stunts over the vibrations from the enormous speakers. And I loved Smithers’ runner where, after being sent to coldest Canada to procure ice for Burns’ own, abortive party (“A quarter ton of lake ice. Hand sawn and tong carried.”), he’s shown on a Jack London trek that eventually pits him against wolves, bears, moose, a bear throwing a moose at him, and an unruly French-Canadian biker gang, before finally showing up as Burns’ and Jay G’s life-saving deus ex machina. (Mostly melted ice makes a fine cushion when plummeting from a falling chandelier.)


But the whole rap element is what was most questionable going into this event. The Simpsons has incorporated music just fine over the years, but there has also been… unpleasantness when the show has attempted to squeeze its sensibilities into musical genres outside its traditional scope. (To be fair, the show has mocked its own musical merchandising pretty memorably.) But the rap songs in “The Great Phatsby” are co-written by Empire’s Jim Beanz (with Greaney), and meld Beanz’s beats with the show’s signature humor unobtrusively enough to be tuneful and funny. Look, The Simpsons is not the hippest show in town, and all the Harry Potter and Lord Of The Rings references are balanced with fine, energetic performances from Key and Richardson. Not to mention Common, Snoop, and RZA, whose verses on the anti-Jay G diss track see them complaining about how, for example, he stole Snoop’s handyman before his gazebo was finished and crashed Common’s jet ski. Any fears that we’d get “Rapping Homer” are, thankfully, dashed, with the show poking fun at its own signature whiteness in Homer’s enthusiastically clueless response to Jazzy James’ song. (“Whoa! It rhymed!”) Sure did, Homer. It sure did.

(Photo: Fox)
(Photo: Fox)

In the end, this star-studded ratings event is just a decent, minor-key Simpsons episode elevated more by performances, skillful and ambitious animation, and some good jokes than by either the Gatsby or “Simpsons rap” conceits. Yes, Marge forgives Homer for lying to her about going back to work at the plant rather than helping Burns by praising his “heart as big as The Ritz.” But her offhand dismissal of Lisa calling attention to the reference (“I did graduate high school.”) sums up just how important all the Fitzgerald-dropping is in the scheme of things. Better are the inventively silly jokes, like Jazzy James only being able to write when Homer reenacts Jay G’s tactic of dangling him (alleged Suge Knight-style) upside down out a skyscraper window. (“Why does this work?!”) Or Lisa’s rich little creep suitor complaining about the time he had to eat supermarket sushi. (“The shiso leaf was plastic! It’s plastic!”) Or the Twilight Zone ending of Marge’s adventure in boutique retail, where the New England-y old timer who hangs all the trophy wives’ store signs lets out a maniacal laugh as one more wealthy woman starts talking about her plans (bookmarks, wicker) for a recently empty shop. While the “event” status of “The Great Phatsby” is overblown, it’s nonetheless a perfectly enjoyable episode in its own right.

Stray observations

  • I am, as ever, a sucker for old-timey Burns-isms. Accepting the obsidian card Jay G uses to steal his money: “A charge plate? But I’ve never had one of those newfangled swipe-a-ma-jigs!”
  • And, after coming to grips with his credit card failure: “I handled it as well as a freshman at Michigan State.”
  • Naturally, Burns swears revenge on the names of the Ancient Ones, bellowing, “I swear on the squid beak of Lord Cthulhu and all his briny shoggoths!”
  • Even Burns’ slimy lawyer deserts him for Jay G. “Sign this release legally releasing the hounds. If you don’t, Mr. Jay G will release the hounds.”
  • Smithers, before his Canada adventure: “I have 45 close friends who are all pretty amazing party planners.”
  • “Affairs were launched on my dance floor, and were consummated on my floor-floor.”
  • “My eyes were clouded by the cataracts of excess. And an excess of cataracts.”
  • Homer’s assessment of Middle Hampton, “Where mansions are called cottages, and getting drunk on a boat is called sailing.”
  • “And so was forged the most unlikely of friendships. The man who discovered Rick Ross and the man who dated Betsy Ross.”
  • Hank Azaria makes rich boy Blake uniquely, comically hateable before he disappears at the end of the first episode half of this hour-long extravaganza. After Lisa calls him out for cutting the line at the ice cream parlor, his supercilious offer to buy everyone’s cone (“Is that okay, does that make it okay?”) is just right in its utter disconnect from actual human feeling.
  • Lisa, shutting down Blake’s come-on: “I would never accept an ice cream from someone whose manners are in the bottom one percent!”
  • “For her I gave up what meant most to me. Being a douche.”
  • Milhouse is Springfield’s resident expert on rap. Even Common recognizes.
  • Homer is continually assaulted by Jay G’s pet goose, Goosius. Having house-sat for someone who had six geese once, I can confirm that geese are fucking assholes.
  • Marge’s shop (probably “shoppe”) story doesn’t have much going for it, ultimately. But the names (“Peppermints and Pussy Willows by Marge,” “Next Doorables,” “Lavender Zeppelin”) are all chillingly familiar to anyone who spent summers in quaint villages. Also, I can see a lot of people clamoring for handbags made from the covers of old jukebox speakers.
  • “You can’t cobbler pineapple!” “Yet here it is.”

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