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Herring is such a pioneer of British online comedy that it's easy to forget his first break came pre-internet, on BBC Radio in the early 1990s with erstwhile comedy partner Stewart Lee. The pair would go on to co-write and star in Fist of Fun, a sketch show first on Radio 1 and later BBC Two, before riding the alternative comedy boom to land a Sunday lunchtime slot on BBC Two for the anarchic This Morning with Richard Not Judy – an adult take on This Morning for the comedown crowd.

Even then, there was acknowledgement that a then-primitive internet could be used to engage a young and tech-savvy audience, with a request every episode for viewers to email "LeeandHerring@compuserve.com". Since the pair drifted apart as a double act, the internet has become increasingly important to Herring. He was described by Russell Brand as a "buccaneer on the fringes of a cyber-world" and has garnered a cultish following of slightly nerdy, left-leaning men who work in IT – a group upon which he relies, but still never tires of mocking.  

Thanks to their support, he's been given the freedom to embark on a number of crowd-funded online projects. This includes Richard Herring's Leicester Square Theatre Podcast, a one-on-one chat recorded with fellow comedians and released for free on YouTube, and the stand-up and sketch show As It Occurs to Me. The success of these projects also allows Herring to indulge in more esoteric pursuits, such as Me 1 vs Me 2 Snooker, a podcast in which he plays snooker against himself and commentates on the action.

But snooker isn't the only game in which Me 1 and Me 2 do battle. Another Herring favourite – references to which are sprinkled throughout podcasts, stand-up shows and tweets – is Addams Family Pinball. And so to lure him for a chat, I tracked down a working table – a relative rarity – in Richmond's The Bear Kick.

Even as someone who's not well-versed in the game of pinball, the table is impressive. The 1992 machine is often pointed to by enthusiasts as being best-in-class, and is considerably more layered and skill-based than I had realised. Far more than a simple game of mechanical keepy-uppy, it encourages players to aim precise shots at specific bumpers and targets to rack up points – the ongoing goal being to light up all the windows of the Addams Family mansion.

"I think it's the greatest achievement of humanity, I genuinely do," Herring tells me, launching his first ball. "This is order and chaos."

Herring is serious about the pinball table's contribution to civilisation. In fact, he explains that he's never understood why certain pursuits are arbitrarily considered worthy or artistic, while others are somehow less acceptable. A good example would be his recent staging of Me 1 vs Me 2 Snooker at a performance art event in Hackney, which was dubbed "an excruciating experience of unbearable length" by Incident Magazine amid several walk-outs.

"It was amazing to do it, and it was amazing that the art people were all snooty about it," he reflects. "They were all doing things like shitting in bags… transgression doesn't have to be that obvious, does it?"

The Me 1 vs Me 2 concept is, after all, deeper than simply pushing the boundaries of entertainment. "As a kid, I played a lot of games by myself," explains Herring. "Anyone who was a bit of a lonely kid and had to while away time playing games by themselves will understand. It's about how all of us divide into two people."

Herring has become visibly frustrated by his failure to play Addams Family Pinball to the standard he knows he is capable. Skills honed on the iPad version prove difficult to transfer to a physical table, especially with me looming over his shoulder and firing off questions.

Herring is both a pendant and a perfectionist, and much of his comedy, and his foibles, come from that obsessiveness. "A lot of it is about repetition and being irritating," he says. "Both me and Stew [Lee] were kind of fascinated by that, but I think I've lived it more than he has. There's the slight obsessive thing that fuels what I do as well."

"If World War II hadn't played out exactly like it played out, none of us would be alive. So we owe our lives to World War II."

In his stand-up Herring tries to work out the genealogy of Jesus Christ and the reasoning behind "There Was an Old Lady Who Swallowed a Fly", pushing them to their furthest logical end point. "What she's doing is swallowing slightly larger predators of the previous creature – a bird is a predator of a spider, that makes perfect logical sense. Some of the choices she's about to make are ridiculous. Do not go bandying the word 'absurd' around at this juncture."

This obsessive edge is something that shines through not just in the nature of his work, but also the manner and sheer frequency in which it is delivered. Recording a daily blog for nearly 15 years, Herring says, "is the craziest thing I do. That's the thing I worry about being insane."

Another of his long-standing obsessions is with time travel fiction – specifically, its inaccuracies, which he is aiming to address with his new sitcom Everything Happens for No Reason. The series is based around parallel universes, with the principal characters able to travel not backwards or forwards in time, but sideways between universes – some only slightly altered, others significantly.

A non-broadcast pilot has been recorded for Channel 4, starring Noel Fielding as "an immortal, inter-dimensional being composed of fire" alongside Jessica Knappett and Ben Bailey-Smith, but its future is yet to be decided.

"I wanted it to make logical sense, which I think most time travel stuff doesn't," says Herring. "I get very annoyed about time travel stuff that something changes in the past and then a few things change in the future. Anything you change would change everything. If World War II hadn't played out exactly like it played out, none of us would be alive. So we owe our lives to World War II."

I am surprised just how much his penchant for over-analysis features in our conversation, and how authentic it seems. There's a genuine curiosity and desire to unpick concepts and ideas evident in Herring that would be irritating if it weren't for his self-awareness. But as with his routines, by spending so much time and energy tackling disproportionately trivial matters, he makes himself the butt of the joke.

It's a busy time for Herring right now, as he also begins his new tour, The Best, which features his favourite routines from previous shows, including his take on the Bible's opening page from 2011 show Christ on a Bike and the racist liberal routine from 2010's Hitler Moustache.

"I've concentrated more on the older ones, because I sort of feel like the people who've been coming to see me don't necessarily want to see the show I did last year," he tells me.

However, no material from 2005 show Someone Likes Yoghurt is likely to make the cut. That was Herring at his most divisive and patience-stretching, spending more than half the show analysing a comment made by a supermarket checkout worker about the nine yoghurts in his basket.

"That was partly about bringing people out to irritate them and deliberately stretching that so long that they're annoyed," he recalls. The Telegraph named it the worst comedy experience of 2005, describing it as "The kind of comedy that makes you want to scream, but not with laughter." This was something Herring previously wore as a badge of honour, but since the birth of his daughter, he now has a newfound appreciation for how rare and sacred a night out at a show can be.

"If people are coming out and they're paying to see me, I'd like them to have a nice time."

Even as we round off the interview and leave The Bear Kick, Herring is kicking himself over his failure to register a high score on The Addams Family pinball. He ends up locked in a discussion with the landlord, a pinball enthusiast of a similar age, who says he can come back and play anytime.