With the exception of my Yahoo Tech colleagues, John Oliver might be my favorite commentator on contemporary technology.
Yes, John Oliver — the Daily Show veteran, stand-up comedian, and now host of his own comedic news show, Last Week Tonight.
Oliver’s tech-related segments, however, are great examples of what he’s doing so well. Moreover, a major part of what makes these segments so effective is the way the show has cleverly — and perhaps counterintuitively — taken advantage of contemporary tech culture to spread its message.
The program airs on HBO (which limits its audience) but has quickly become a sensation through shrewd use of our Web-era friend the viral video. By itself that wouldn’t be too surprising: Lots of comedy sketch/talk shows have figured out the power of pushing short, quick-hit bits into the online realm to reach a different audience.
Many of Oliver’s biggest Web hits, however, have been very lengthy clips — some addressing a single subject for the better part of 15 minutes.
Think about that: In an era when many of us think of video as a snack-size option to scarf on a mobile device, these clips are practically the information-age equivalent of a lavish multicourse meal.
Consider this recent segment (below) about one of the most controversial and confusing technologies of our time: military drones. It’s a tough and not particularly funny subject — yet this 13-minute video has racked up more than 3 million views.
So what’s the secret sauce here? I’d say it’s a combination of classic comedic technique melded with a surprising level of earnest journalistic effort, packaged for an audience that really does want to know more about the serious topics of the day — if only the information can be presented in a manner that goes down easy.
Tension and release — and research
There is, obviously, nothing inherently funny about deploying weaponized machinery with names like Predator and Reaper to the other side of the world to kill our nation’s enemies — and, in the process, not a few innocent civilians.
But when Last Week Tonight chooses tough topics as the focus of its long-form segments, it’s tapping into a comedic tradition: From the social critiques of Lenny Bruce through Tig Notaro’s masterful set dealing squarely with breast cancer and personal tragedy, many of comedy’s most creative practitioners have shown how to balance the tension of challenging ideas with the welcome release of laughter.
Watch the drones segment, and you’ll see a speeded-up version of this in action: You stick with Oliver through stretches of troubling, laugh-free material about how the government determines when a drone strike is allowable — and when a punchline emerges that draws a ridiculous comparison to Harvey Keitel’s nether regions, it’s not so much funny as a relief.
This is an example of how the long-form approach can actually be a strength: The pace never lets up, but working with a bigger chunk of time lets Oliver build momentum. And once you start watching, it’s surprisingly hard to stop.
Along the way, the segment taps into the great power of comedy to reveal absurd “logic” — like the idea that a target might be “appropriate” even if his identity can’t be confirmed, or that an “imminent” threat doesn’t necessarily have to happen anytime soon.
The second element of the formula that makes these videos work is more contemporary: We all know that predecessors like The Daily Show and The Colbert Report aren’t just funny, but surprisingly well reported. “We spent a lot of time this week trying to find some concrete answers to basic questions,” Oliver says toward the top of the drone segment, “and it’s surprisingly difficult.”
This turns out to be convincing as the piece unfolds: It draws heavily on mainstream media coverage, but cherrypicking from the earnest stories that, let’s face it, many of us ignore. And although I’m a fairly engaged consumer of drone-related news, it included material that was certainly new to me — from an Iranian English-language news network reporting on drone strikes to the president joking that the Jonas Brothers had better not get any ideas about taking advantage of his daughters’ fandom — “Two words: Predator drones.”
It’s easy to imagine any of these bits being the centerpiece of a much shorter clip. But stack them together, and it turns out the results are more than the sum of their parts.
A recent Rolling Stone cover story on Oliver — I told you the show is hot! — notes that the show’s producers have expanded its research staff “to keep up with their escalating ambitions” around these longer-form segments.
(As combo relevant side note and disclosure: Last Week Tonight’s executive producer, Tim Carvell, was a long-ago colleague of mine at Fortune, where he was a young hotshot known for his writing skill — and his reporting chops. He’s also the former head writer of The Daily Show; looking back, I wonder if his real insight was figuring out early that the best journalism jobs are actually in comedy?)
“We could do longer”
According to that Rolling Stone story, Oliver and his crew stumbled onto the longwatch formula by accident — struggling with an overly long segment concerning the death penalty, Oliver told the magazine, they simply concluded it would be “ridiculously funny” to experiment with giving a lot of air time to an incredibly non-comedic subject. The reaction was positive. “So from then on, we started opening up a bit, thinking, ‘Well, we could do longer.’ ”
In the context of media and entertainment in 2014, that’s a classic case of a zig when everybody else is zagging. We all know that the media has, for as long as any of us can remember, defaulted to shorter sound bites, or reducing ideas to lists and quizzes. Nobody believes we can pay attention to anything for 15 minutes. And, yet, here is proof that we can.
In fact, I’d say the third element of the subsequent success is choosing topics that are hard not because they’re controversial (like drones) but because they are, often, deadly dull. (The show’s most recent longwatch segment was about … civil forfeiture.)
Another breakthrough example along these lines also happened to concern technology: a long piece on the notoriously interest-proof subject of “net neutrality.” My colleague Jason Gilbert praised this segment back in June. All I can say is, if you think you can’t possibly endure 11-plus minutes on the subject without your head conking onto your desk, watch this video — which has 6.2 million views:
The piece copes with its own potential boring-ness by comically empathizing with the audience. (“If you want to do something evil,” Oliver declares, “put it inside something boring.”) And with an absurd bag of comedy tricks not available to traditional journalists — like explaining how Oliver’s hypothetical Nutflix service could suffer unfairly.
In another break with straight reporting, Oliver can overly call B.S., or compare Comcast’s behavior to that of a Mafioso, in a way that, I don’t know, Wolf Blitzer or Brian Williams or whoever, just can’t. The upshot is an informative argument not just about why net neutrality matters — but why you should actually be emotional about it.
The show is just as good on another eye-glazing Web-culture issue: so-called “native advertising” — how the lines between journalism and marketing are getting blurrier, and why that matters. The video runs over 11 minutes and has 2.3 million views:
Rolling Stone says Oliver is “mad as hell,” but I’m not so sure I buy that. I think he’s baffled, exasperated, and (this is the important bit) completely engaged. He comes across as a guy who is really trying to figure out what the hell is happening.
The show’s gamble is that, with Oliver as our guide, enough of us viewers feel the same way. So far, it’s winning.