It can hardly be said that there’s a shortage of formidable talkshow hosts in 2018. If anything, the form has undergone a renaissance thanks to Donald Trump, who’s provided for late-night television a salvo of punchlines and a new jolt of life. Those who’ve chosen to more brazenly address his presidency, like Stephen Colbert and Samantha Bee, have benefited enormously as a result, while hosts like Jimmy Fallon, who takes a more chirpy, apolitical approach, have seen their ratings dip.

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But ever since Colbert took over the late-night slot at CBS in 2015, there’s been a glaring void in the genre left by the departure of David Letterman. When he returns on Friday, with a new long-form talkshow on Netflix and a Gandalfian beard born of temporary retirement, that void will be filled. One way to measure the tectonic significance of Letterman’s comeback? His first guest will be none other than Barack Obama.

Throughout his nearly three-year absence from television, Letterman insisted repeatedly that he didn’t miss it. But perhaps the opportunity to get back in the game by way of a streaming service convinced him he did. On My Next Guest Needs No Introduction with David Letterman – a mouthful of a name – Letterman will sit down with the likes of Obama, Jay-Z, Malala Yousafzai and Tina Fey, conducting interviews and field pieces. The bite-sized first season will consist of six episodes, released monthly, and the more open-ended format should be an ideal display for Letterman’s talents, which in 30 years of late-night television never waned; he can play the irritable curmudgeon, the hard-nosed journalist and the affable jester with equal dynamism.

But it remains to be seen whether Letterman can match his past success on a new, less procedural platform. He won’t be the first comic to take his talents to a streaming service: Chelsea Handler and Sarah Silverman have attempted similarly structured shows on Netflix and Hulu, respectively, with middling results. Handler’s eponymously named talkshow, which she launched with the express purpose of moving away from celebrity gossip and towards more socially conscious subject matters, was a mixed bag, often funny but generally pedantic. Handler’s show was cancelled late last year after two seasons; its host has resolved to become more engaged politically.

Silverman’s venture had similar intentions: with I Love You, America, the comic brought her brand of urban, Jewish humor to the heartlands to find some common ground between Trump voters and the “coastal elites”. It’s a quick, compassionate show, but it’s yielded little publicity or viral clips on YouTube which, for better or worse, is about the only existing barometer to measure the success of a streaming program such as this.

Though neither shows were entirely unsuccessful, they also weren’t disruptive forces. Where Jimmy Kimmel seemed to effect real change in using his show as a soapbox to discuss the Affordable Care Act, Handler and Silverman were stymied rather than liberated by the sheer volume of entertainment offered by streaming services. Each had a difficult time standing out.

Letterman’s series will have a leg-up thanks to its inaugural guest; the interview will be Obama’s first talkshow appearance since Trump took office, and if anyone can coax the famously diplomatic former president into candor, Letterman would be the safest bet. Ever the raconteur, Letterman’s hour-long show will allow him to further sink his teeth into whatever he chooses to cover – recent interviews with New York magazine and the Washington Post suggest Trump is on his mind – without the clockwork constraints of network television. The conversational format should also give him space to show off that well-honed balance of sarcasm and curiosity.

Facebook Twitter Pinterest David Letterman in a still from his new Netflix series. Photograph: Joe Pugliese/Netflix

The move to Netflix also places Letterman in competition with longtime counterpart Jay Leno, who bowed out of late-night just a year before Letterman to start his own web series, Jay Leno’s Garage, at NBC online. Of course, Letterman never saw it as a rivalry, but their careers have undeniable parallels. Reflecting on those days when he and Leno went head-to-head in the ratings every night, Letterman told the Washington Post: “It was ‘The Late Night Wars,’ oh, ‘Jay’s winning, nobody likes me, and everybody likes Jay.’ Now I think, what was that? Who’s at war here? There’s no war any more. And I think, why was I in the war?”

Even so, Garage is a far more niche foray into the genre than My Next Guest, since it’s primarily about Leno’s love of cars. It’s an imprecise bellwether for how well Letterman’s show, which has more star power and seems more broadly focused, will fare. Somewhere between both of these projects is Jerry Seinfeld’s Comedians in Cars Getting Coffee, which also streams online and, as its self-explanatory title would suggest, is an amusingly relaxed half-hour low on production quality but high on charm.

With Netflix in his corner, Letterman’s new series will have both. And although the platform doesn’t release viewing figures for its programs, there’s been enough hype for Letterman’s return to suggest fans will be logging on at midnight on Thursday to watch the premiere (or, at least, to see Obama).

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A lot has changed since Letterman last hosted The Late Show. Although he was never particularly strident when it came to politics, digging into Trump is now something of a prerequisite to having a successful talkshow. But that shouldn’t be a problem, either.

Not only does one imagine he’s champing at the bit to talk about the state of the union, but Letterman’s relationship with Trump goes back three decades, having soured after Letterman pulled one of his guest’s branded ties out from behind his desk and told Trump, who seconds before had been railing against China for taking American jobs, that his ties were made – where else? – in China. The ensuing silence showed Letterman’s unique ability to combat boorishness with snark and wit.

While Letterman, in a far-ranging conversation with Vulture, strayed from criticizing Jimmy Fallon’s notoriously lightweight interview with Trump, he did hint at how he’ll approach the subject on his own series: “I don’t want to criticize Jimmy Fallon,” he said, “but I can only tell you what I would have done in that situation: I would have gone to work on Trump.” And while Netflix hasn’t proven itself to be an ideal destination for talkshow hosts, talkshows have emerged as ground zero for a good presidential skewering; it’s hard to think of anyone better equipped than Letterman to make those ends meet.