Sideshow Bob is wasted in a Simpsons holiday episode with no reason to exist
“Just general Scrooge-iness.”
Bah, humbug, and happy holidays filled with suspect mall Santas, decorated Buddha statues, dreidel roulette (always bet on shin), and all your family’s commercialized religious foofaraw. Toss in some not especially effective celebrity cameos, two-to-three (maybe four) plots hastily whammed together, and a truly baffling amount of ends credits filler, and you’ve got yourself a latter-day Simpsons Christmas episode! Ho, ho, humbug.
“Bobby, It’s Cold Outside,” (title referring to one aforementioned credits filler gag) at least sees everyone’s favorite ineffective psycho would-be murderer back in town for the holidays. Of all the recurring, non-cast characters, Bob’s the one most likely to brighten up my day/any episode, simply due to Kelsey Grammer’s obvious joy in the villainous role. (Plus, they always let him sing—put “Carol Of The Bells” on your Sideshow Bob mix CD.) The never-to-end saga of Robert Underdunk Terwilliger’s bloodlust for the blood of one Bart Simpson stretches all the way back to The Simpsons’ 12th-ever episode, and he’s been swinging and whiffing hard for some 29 years at this point. Like most recurring characters and bits, Bob’s appearances have waxed and waned in comic effectiveness, but, hey, always nice to have Grammer in the house, once more essaying his second-most(?) famous role.
Sadly, the ravages of time haven’t been kind to Bob (either as character or plot engine). Holed up as a lonely, murmuringly homicidal lighthouse keeper come Christmastime, we see Bob fending off the advances of a lonely woman named Cassandra, a muffin basket-toting romantic interest whose main role here is to spur flashbacks of Bob’s obsession with Bart, and how he escaped from prison this time. (Simple head-clonk and unobservant guard.) Perfunctoriness is less of of problem when Bob’s in town (just get to the scheming), although couching Bob’s villainy in some sort of psychological framework makes for better homicidal near-misses, and that’s where “Bobby, It’s Cold Outside” falters out of the gate. Rushing past Cassandra (just as the uninterested Bob does), the plot sees a couple of unexplained guys drive up to recruit Bob to be a mall Santa. Okay, so get Bob into the red suit and let’s get rolling, I guess.
Then there’s a parallel plot where someone’s stealing all Springfielders’ holiday deliveries from their front porches (including one poor unfortunate’s porch repairing kit), a development that’s left to sit out in the cold for a while. Lenny takes the lead on this one, which, hi Lenny. Meanwhile, Marge scuttles Homer’s amorous plans for some snuggling to Roma (boy, will he be disappointed it’s not about the ribs guy), demanding he take the family to Santa’s Village in Ogdenville. And, we’re off! Collision course for Bart and Bob! Thrills! Chills! Excitement?
Bah. Instead, Bart—cutting line, because he’s such a scamp—winds up in Bob’s clutches, only to escape without incident because Bob’s a Method actor and has decided that Santa wouldn’t kill a little kid, even if that kid ruined his life countless times. Sure, Bart clonks Bob unconscious with a giant sucker, but nothing comes of that, as Bob’s Santa union ID lets him walk (despite being an escapee from prison?), so he can help the Simpsons solve the UPS delivery thefts? Allll right . . .
See, Lenny (after blowing himself up with a homemade gunpowder and ink thief-trap) manages to scrawl the initials S.B. on his own porch, leading Bart to suspect Sideshow Bob, and Wiggum to suspect, arrest, and then release those not especially effective guest voices, grumpy Scott Bakula and ebullient Seattle billionaire and Los Angeles Clippers owner Steve Ballmer(?) (Plus a silent Sandra Bullock, shown doing a Bird Box reference, which, okay.) The Simpsons quickly invite the multiple attempted murderer of their son into the family home without anything resembling a reason, then follow the boxed-up Bob as he’s stolen by the package bandits, leading to the revelation that S.B. is, um, Smithers and Burns? “When did Smithers start going first?,” asks Homer concerning the tortured logic of the denouement in the one funny aside of the episode.
There’s a feint toward trying to wring some emotion out of Burns’ initially motive-less petty crime spree, with Lisa probing a bit deeper, causing Burns to spill concerning his unloving parents, a Santa’s lap wish for “a hug and a smile,” and the eventual crushing disappointment that—in this episode’s version of history—sent young Monty down the road of ruthless, plutocratic supervillainy. Bob takes a whack at it, too, tossing on a convenient Santa suit to recreate Burns’ childhood memory palace and convince Springfield’s oldest, stingiest, and Scrooge-iest rich jerk that his parents’ coldness (instead of the wished-for tokens of affection, young Monty got shipped off to his first boarding school on Christmas morning, 1935) is what prepared him to be the miserable but rich old fart he is now.
As Christmas messages go (“You’re the richest man in town because of your parents’ love”), it’s some suspect stuff, which could come off like a joke-reversal of It’s A Wonderful Life (which we see Bob watching later), if not for how “Bobby, It’s Cold Outside” doesn’t set up any sort of stakes for Burns’ tacked-on journey, and, indeed, because the entire episode is one of those simultaneously overstuffed and under-baked heaps of nothing that whatever Christmas warmth you derive from it comes from the generosity of the season. The Simpsons can focus up and tell a coherent story from start to finish at this point, but, man is it rare. Here, events pile up, rather than build, and, for all the indifference Bob shows toward his singular mission in life, the fake Santa role could have been played by Lenny, for all it matters. Grammer gets so little chance to do his thing in this outing that it’s doubly disappointing. Bob usually perks things up.
And then there’s the damnable ending, where the episode’s slapdash dashing gives way to three—that’s three—lengthy tags that add exactly nothing to the main story. Burns meets Ballmer at the airport, where their billionaire-to-billionaire talk results in Burns bucking back up about being “rich beyond any sense of justice.” There’s a neat, brief bit of head-animation when Burns is unable to meet the enthusiastic Ballmer’s gaze.
Then Bob and Cassandra finally get together (hey, that’d be something more interesting for Bob to do, right?), when the seemingly clueless woman reveals that she knows exactly who Sideshow Bob is—and she’s into it. Singing a knowingly updated version of understandably out-of-favor duet “Baby, It’s Cold Outside” (Cassandra brings along a signed letter of consent), the two dance their way toward some romance, which helps Bob get over whatever feelings his nondescript adventure could have left him with. Plus the pall cast by Cassandra’s proffered gift of a rake.
And then the writers room gives us a series of joke holiday cards featuring Simpsons characters that I defy anyone on this planet to respond to with anything but forbearing recognition.
As a Simpsons Christmas episode, as a Sideshow Bob episode, “Bobby’s It’s Cold Outside” is a lump of especially dull coal. Bah.
Stray observation
- The Simpsons tune in to the Fox News Yule Log, which consists of a pile of burning books and documents (Darwin, Rachel Carson, the Bill Of Rights, the Constitution, Emily Post). Take that, corporate master propagandists.
- Burns, asked about the fates of most of his aristocratic colleagues, pronounces, sadly, “Broke, dead, a lot of hashtag Me Toos.”
- Nobody but Grammer could land a line like his excuse to Cassandra, “My gimbals need whale-oiling.”
- It’s always jarring when someone on The Simpsons is watching an actual, live-action movie. Stop it.
- Maggie gets plopped down on a truly terrifying, gnome-based ride patterned on that Elf On A Shelf nonsense, which is also genuinely terrifying. Stop it.