Revisiting Political Comedy: Self-Medication Through Old Jokes

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At the end of 2017, I’m doing something for mental health that most people might not consider, because it’s honestly a system I’m not sure how I fell into. I don’t even know why I thought it would work. That thing is the process of starting to work with background video/audio from old political commentary/comedy shows. Mostly, the first two seasons of Last Week Tonight, and then some podcasts, and occasionally old Daily Shows or episodes of Samantha Bee’s program from the first season. My entertainment, and my relaxation, has been transitioned into finding humor and insight from before the Trump presidency.

I feel like I’ve spent all of 2017 trying to kick the feeling that we are in the bad timeline. There was a distinct belief I instilled in myself that by reading the post-mortem on the Clinton campaign in the book Shattered that I would somehow finally let my last primal shouts be released and I would be free of the chains of the 2016 election. Or at least I would let the final burst of anger screech from my plummeting soul. Well, that book did nothing to subside my anger. Nor did showing up for events. You know what absolutely didn’t help? Working a voting location the entire day of the election, in hopes my wife and I would later celebrate our contribution to the concept of Democracy.

This has been a wound without closure and I’ve started trying experimental medicine to get the hemorrhage from bleeding out.

With that in mind it is perhaps not a surprise that I would retreat to entertainment that focuses on the news that happened under a better president. And yeah, I understand that this seems like some kind of escapism or flat-out denial. Look, it’s not like I started writing 2015 on my checks and recycling newspapers. I’m not insane. (Insert some gif of Dwight from The Office into your brain at this moment.) Instead, it was just a nice reminder of what outrage culture used to look like, before every moment was on fire.

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Jokingly, it’s a nice reminder to revisit a time when the most outrageous things we could shout about was bird dialysis or the gerrymandering of prisons. That’s a lot of what revisiting season one of Last Week Tonight is all about: We used to need to get angry about the space between structures. Whenever Obama comes up on the show, it’s not to assault him for destroying democracy, but rather to hammer him for small mistakes between the real fine print.

Still, that makes me feel good. It’s that same magic that draws you back to Leslie Knope: this nerding out over footnotes in legalese and realizing that that’s where the real battles get fought. And a return to the time where it was transgressive and rebellious to battle on the sublevel makes me feel better than remembering we’re in a period of fighting language on the bolded headline level.

For example, starting into Last Week Tonight from the beginning, like with any show, is initially an exercise in realizing how far it’s come in figuring out its own structure. The first season is plagued with side-segments that go nowhere but have their heart in the right place—usually the bits where Oliver has to interview smart people and they shit on him and he acts upset about it. Beyond that, most of the episodes (from the beginning) knew that they could fill an entire hour and therefore put their extended interviews and such online. Season 2.5 of the show is when the show started to shit on the 30 minute limitation and break out into forty minute plus episodes and it wasn’t until season 4 that it really pulls back into 30 minutes every week.

As a journey through time, the very first episode of the HBO weekly show opens with a series of jokes about Donald Sterling demanding his wife not take Instagram pictures with blacks, and puts that up against footage of Cliven Bundy, long before Bundy’s stance inspired some assholes to occupy a bird sanctuary. This is emblematic of everything that happens here: you see the first DNA strands of… no wait, the first sweater threads being pulled from the shit that will become The Shit in the years to come. It’s amazing to watch the focus fall onto the small pawn assholes that would serve as launching points for bigger, more awful death marches into The Sunken Place. It’s genuinely amazing to remember that this also began with Cliven Bundy, who could now perhaps hold political office. This was, of course, just after Chris Christie’s Bridgegate and folks still considered him A Contender.

The first episode then sinks its time into both the hyper-politicized Indian elections that became lost behind partisan shouting (foreshadowing) and then into James Clapper trying to explain that the NSA is not monitoring Americans (just before this would become The Biggest Issue). In what would be the least long-running bit on the show, Workplace Of The Week focused on NFL cheerleaders and their poor pay, lackluster coverage and hellish working conditions. I can see why this one died early. Not because it wasn’t progressive and aware, but because all of America has become the worst possible workplace.

From here, the next few episodes include Obama and Angela Merkel having a pleasant conversation, which is now brutally funny in the wake of Trump refusing to shake Merkel’s hands. But overwhelmingly, Last Week Tonight has to turn to foreign issues. The election in India is a start but one of the biggest early segments is reserved for the Sultan of Brunei because THATS HOW DEEP WE HAD TO DIG FOR CORRUPTION.

But there is also this upswing of joy. Oliver covers EuroVision when a transgender singer takes home the win and between that and the NFL drafting of Michael Sam, he shouts to camera: “Did the world feel like a better place to live this week?” And at the time it usually did. There is, perhaps central to why I was brought back here, a sense that we were on the up-swing.

There’s also so much foundation being laid for the wars to come, and this is the unbelievably hard part about revisiting this show. Season 2, which feels too late, often leans on the joke that the Presidential election is so far away that even discussing it is a waste of time. That said, even the beginning episodes of season 1 shit on Trump because, as it will not surprise you, most media has always shitted on Trump. Because he has always been shit and deserving of shit commentary. Hell, even Scrooged takes a few shots at him.

Early episodes also feature Mitch McConnell declaring war against the rest of the United States on behalf of jobs for coal miners. This seemed hilarious at the time, until Trump won from shoving this narrative. Equally humiliating, if not more so, is that Last Week Tonight sought to bring Russia/Putin and its influence to the forefront (seriously) every other week. From the capture of Ukraine forward, this show never looked away from what was happening. It is heartbreaking to see how much forewarning was on display here.

But also: you remember when Julianne Hough wore blackface to a Halloween party when portraying Crazy Eyes from Orange Is The New Black? That was once something that we tried to muster equal outrage for versus Crimea. Opposite that is climate change denial (featuring Bill Nye the Science Guy) back when we were so much further along in the climate change conversation. If there’s anything in Last Week Tonight that breaks my heart, it’s the moments where we seemed to be having conversations three years ago about how to handle the last few meters to the summit, whereas our current administration has us back at base camp.

Equally, there are early rumblings of Europe leaning into the far right, which gets dismissed as very Nazi-ish and therefore easy to dismiss, ahead of Brexit and our own right-leaning defeat. There are plenty of weird-choice based bits, like a Tamagotchi Life civil union cheat code CGI bit featuring Toad and Yoshi making out, or a remake of An American Tale that leaves me with uncanny valley chills. But yeah, that weird lean into the right is terrifying. Because via the comedy show that first makes fun of this happening abroad and then makes fun of it happening at home, you can see where the dismissal lived. And no, not within the show itself, but within all narratives around it. In fact, more than anything it confirms that idea that 2015-2017 were the years of the world leaning into “What about shaking things up?” or “Wouldn’t it be funny if this happened?” And now we all have to deal with the fallout.

This experiment in mental health started strong and enjoyed a long period of hours of being able to appreciate excellent joke structure, often dragging societal ills that have been corrected. The unfortunate part is that the largest, overriding issues are where this all failed. There are all these small line-items where real progress was made and often on behalf of this show and how it could go full-Spotlight on technicalities. But the erasure of letting an asshole become president and ushering in a new era of neo-Fascism means making peace with the loss of most of the victories. What began as a chance for the occasional societal victory lap became a greatest hits reel of what we lost.

It’s still funny though. Whatever that’s worth.

Brock Wilbur is a writer and comedian from Los Angeles who lives with his wife Vivian Kane and their cat, Cat. He is the co-author (with Nathan Rabin) of the forthcoming book Postal for the Boss Fight Books series.