The Simpsons: "Sideshow Bob's Last Gleaming"
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The Simpsons: "Sideshow Bob's Last Gleaming"

Sideshow Bob steals the show—oh, and a nuke.

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The Simpsons (Classic)

"Sideshow Bob's Last Gleaming"

Season 7, Episode 9

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“Sideshow Bob’s Last Gleaming” (season seven, episode nine: originally aired 11/26/95)

Wherein Sideshow Bob thinks we’ll meet again, don’t know where, don’t know when…

As Erik pointed out last week, The Simpsons’ season seven boasts some of the deftest blending of heart and laughs in the show’s storied history. Episodes like “Mother Simpson,” “Bart Sells His Soul,” Lisa The Vegetarian,” “Marge Be Not Proud,” and “Lisa The Iconoclast” exhibit a mastery of shifting comic tone so assured as to cement this season’s legacy as not only one of the best in Simpsons history, but in sitcom history. Another reason for the acclaim is an episode like “Sideshow Bob’s Last Gleaming,” which exemplifies another classic Simpsons’ skill—that of smacking big, outlandish yuks into the cheap seats, this time with the MVP assistance of returning pinch hitter Kelsey Grammer as Sideshow Bob.

Some might mark this as the point where, as Smithers might say, Krusty’s former sidekick “crossed that line between everyday villainy and cartoonish supervillany,” but it’s not like it was a huge leap for Bob to take, purloined nukes or no nukes, and Grammer’s performance here is truly a wonder to behold. First seen contentedly attempting to maintain his cultural muscles building Westminster Cathedral in a bottle (“Edward the confessor himself could not have done better,” he boasts), the spectacle of Krusty’s continuing lowbrow TV buffoonery (plus that of Vanessa Redgrave spouting “horny grandma” jokes on an American sitcom) finally pushes Bob back over the edge. Stealing away during an outing at air show at the local Air Force base, Bob hijacks a nuke and the Duff blimp, demands that Springfield unplug the TV drug forever, tries to kill Bart (again), actually detonates the (thankfully faulty) bomb, and then kidnaps Bart to kill the defiantly schticky Krusty (broadcasting from a civil defense shack in “the remote alkali flats of the Springfield badlands”). And while it’s all as broad a setup as it sounds, what launches “Sideshow Bob’s Last Gleaming” into classic status (apart from the performances of Grammer and one other guest star we’ll get to), is how sharp and tight the script is. A fact all the more surprising since executive producer Bill Oakley once described it as "one of the most arduous rewrites in the history of the show."

A freelance script from future Seinfeld writer Spike Feresten, apparently the entire season seven writers’ room tore the thing down to its bare bones before cobbling it back together. Disproving the “too many cooks” cliché, all that combined effort team-rewrote this one into a parade ground of non-stop laughs and a playground for Grammer and the rest of the cast, who uniformly deliver some of their strongest—and most specific—performances of the season. Heart is heart, but the sheer volume of great comedy herein is almost embarrassingly generous.

That profligacy of jokes just keeps giving, with one good gag amplified by a seemingly superfluous follow-up. When R. Lee Ermey’s Colonel Leslie “Hap” Hapablap underwhelms the air show crowd with an exhibition of box kites, we get Martin proudly explaining that box kites were invented “as a way of drying wet string.” First introduced as “the pride of the American air force—the British-made harrier jump jet,” the jet gag is subtly followed up with a trio of the planes unobtrusively hovering in order to hear Bob’s ultimatum on the base’s “Tyranno-vision” screen. When Hapablap’s search for Bob turns up nothing but “Porno! Porno! Porno!,” we’re treated to a freeze-frame gag of “Granny Fanny” and (the peerlessly brilliant) “American Breast Enthusiast.” After their failure to shoot down Bob’s hijacked Wright Brothers plane (“Bogey’s airspeed not sufficient for intercept. Suggest we get out and walk”), the pilot’s deadpan pronouncement cuts to two Top Gunners trudging in formation, arms outstretched, behind the ever-so-slow-moving antique. The colonel’s unexpectedly poetic paean to the glory of flight (quoting John Gillespie Magee, Jr.—yes, I did have to look that up), segues into his straight-faced description of flight as “the dream of man and flightless bird alike.” In the Dr. Strangelove-ian war room, Mayor Quimby’s fatuous hypocrisy begins with the self-serious “Our city will not negotiate with terrorists. Is there a city nearby that will?” before he’s given another classic Quimby-ism, “It’s time to face up to the un-face-up-to-able.” And, in a storied Milhouse moment, his furious F-15-seated imaginary strafing of his parents and therapist (“Take that Dr. Sally Waxler!”) ends up with him unexpectedly sent skyward with the ejector seat button. It’s as if, tasked with propping up a tottering script, the collective might of the writers found the desperate mom-strength of a parent seeing her child pinned under a car.

The specificity, too, seems the product of one sure, guiding hand (rather than, as apparently was the case, a crew of flailing, presumably frustrated ones). Rewatching the episode, I was struck by the light touch whereby Lisa’s allowed to solve the mystery of Bob’s whereabouts. In retrospect, I did notice that Bob’s announcement was in a slightly higher register, but it’s not commented upon until scenes later, when Lisa figures out his hiding place in the helium-filled Duff blimp. Similarly, the well-executed bit where Homer reverses the car over the security spikes sets up why he’s unable to catch up to Bob’s barely moving plane. They’re not big things, but the attention to storytelling detail enriches the whole episode. In the same vein, I appreciated how Lisa’s breathless, run-on description of how she foiled Bob’s initial plan is allowed to sound like something a little girl would say. While she remains my favorite character, Lisa’s age-appropriate childishness has been largely missing for a long time now, and I miss it. Here, Lisa’s precociousness coexists with her slightly braggy excitement, and is all the more real for it.

That performance is of a piece with the entire cast in this episode—everyone is just on, delivering lines with a crisp assurance that’s made them endure through the intervening years. There’s Hank Azaria’s tiny role as the no-nonsense tour guide, explaining that the Harrier (“One of our most dollar intensive ordinance delivery vectors”) is so simple a child could fly it. “Can I fly it?” asks Lisa. “Of course you cannot,” he rattles off with staccato precision. (I can’t tell if it’s the same guy, but the soldier who answers Marge’s panicked assertion that her kids are in the locked-down base with the gung-ho “You must be very proud, ma’am” has the same cadence.) There’s the one-line wonder prisoner who answers Chief Wiggum’s “Hey where is Sideshow Bob and that guy who eats people and takes their faces?” with a peerlessly cheery “I’m right here, chief!” And Ermey is used perfectly, his infamous Full Metal Jacket military profanity transformed into a tortured, TV-friendly lingo (“What in The World According To Garp?!”) delivered with a conviction equal to its ludicrousness. (Only the cribbed “What is your major malfunction, Sideshow Bob?” seems forced.) And the timing on the joke where Homer urges Bart to jump onto the Simpsonmobile from Bob’s plane is as adroitly executed as any in the show’s history. (The backpack inexplicably exploding is the perfect absurdist touch of escalation.)

Of course, any Sideshow Bob episode comes down to Grammer, and this is my dark horse pick for best…Bob…ever. What always makes Bob Terwilliger so evocative is the fact that he, homicidal tendencies aside for the moment, is always operating on a thrumming undercurrent of “I’m mad as hell and I’m not going to take it anymore” satire of popular culture—which includes the Simpsons (although not The Simpsons). While not as fourth wall-tickling as Frank Grimes, Bob is always essentially right about what’s wrong with the show’s world, especially when it comes to television (and double-especially when embodied by his former employer/tormenter Krusty). Looking at the opening gag, where Krusty solemnly thanks viewers for their contributions to his canned food drive, only to reveal that he’s used all the donated food to construct a Double Dare-style food obstacle course—it’s hard not to sympathize with poor Bob’s arch disgust with the medium. (Kent Brockman touting his greatest journalistic achievements including stories about “dogs that were mistakenly issued credit cards…and those that were not so lucky” can’t help, either.) Here, Grammer’s delivery of lines like “How was I to think a mere atom bomb could fell the chattering Cyclops?” and “Aviation was a gentleman’s pursuit—back before every Joe Sweat Sock could wedge himself behind a lunch tray and jet off to Raleigh-Durham” pale only next to his legendary appearance on the “Tyranno-vision,” contemptuously taunting the assembled Springfielders with the glorious “Sorry to divert your attention from all the big noises and shiny things.” (I mutter that under my breath almost daily, some 20 years later.) 

And whoever wrote his line (imitating the colonel), “That fool McGuckett sprayed runway foam all over Chuck Yeager’s Acura!” should have gotten a MacArthur grant. Bob’s a lonely, cultured (if pretentious) soul in a world that venerates the likes of Krusty and, watching our own world’s Krusty simulacra, haven’t we all longed to feel our finger linger over the big red television kill switch?

Stray observations:

  • This week in Simpsons signage: 


  • Bob, master of narrative unity: “By the way, I’m aware of the irony of appearing on television in order to decry it. So don’t bother pointing that out.”
  • They can’t all be winners for Hap. After his Garfield metaphor is met with silence: “Sorry, my wife thought that was gangbusters.” I love that he tries out his rants at home.
  • The esteemed representatives of television in the war room: Bumblebee Man, the Fourth Doctor, Urkel, Krusty.
  • “Not the Harrier! We’ve got a war tomorrow!”
  • “Duff and the Air Force: 50 Years of Flying High”
  • Thanks to Erik for letting me take on one of my favorite episodes ever—now let’s haul ass to Lollapalooza!

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