From Stephen Fry on attempting suicide to Mary Beard on goat sex, how does Richard Herring get stars to be so refreshingly frank? And did he go too far with Stephen Merchant?

Michael Parkinson’s greatest failure was that he never asked Muhammad Ali if he had ever tried to fellate himself. Parky’s understandable instinct not to have his face caved in deprived the world of what you can be sure would have been a compelling answer.

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One person who would doubtless have asked it is Richard Herring. His Richard Herring’s Leicester Square Theatre Podcast (or RHLSTP) often includes that very question. Not directed at Ali, sadly, but at almost every British male comedian and personality you can think of. The answer, almost every time, is yes. Make of that what you will.

As crude and juvenile as it sounds, it actually demonstrates two reasons why the British standup comic – whose interview with Les Dennis recently went viral for his tale of a plumber mistaking Dennis’s then-wife Amanda Holden for his daughter – is not-so-quietly becoming the best celebrity interviewer in the land. One: in this age of public relations tyranny and image paranoia, it is refreshing to see a celebrity asked such a shocking and unusual question. Two: it invariably produces interesting answers.

In the case of Herring’s famous interview with Stephen Fry, in which the actor revealed that he had recently attempted suicide, the ‘cock question’ generates by far the biggest laugh of the night, asked as it is right after a Fry treatise on the exquisite pain of adolescent passion. It’s that puncturing of the deferential norms of the celebrity interview that makes Herring so good. And crucially, the question causes Fry to launch into a long and brilliant answer that touches on “the forward curl” technique, the great ballet dancer Nijinsky and former chairman of the Labour party Tom Driberg.

You might think it would only work with a talk show master like Fry, but it seems that self-fellatio makes everyone interesting, either by setting them up for a joke or by embarrassing them into saying something unprepared. In the case of Mary Beard, when asked it about Julius Caesar, it leads to a fascinating discussion about epicurean philosophy and consensual sex with a goat.

Facebook Twitter Pinterest Exquisite pain ... Richard Herring with Stephen Fry. Photograph: Kirsten Mcternan

In his interviews, Herring always affects a slightly exaggerated version of himself as an embittered old comic who resents the success of others. This gives him licence to flirt thrillingly with rudeness. And it begins almost immediately with the introductions. After a not-so-subtle dig at his past excesses, Steve Coogan is “best known as Tommy from The Indian in the Cupboard”. Eddie Izzard is “best known as Reepicheep from the Chronicles of Narnia” and Greg Davies “as Hercules on Nelly Nut Live”. This amusing antidote to the fawning guests can expect on more mainstream chatshows adds an air of exciting unpredictability. However, it can cause trouble such as when, as Herring has admitted, he took it too far when he jokingly introduced Stephen Merchant as a “definite paedophile”. Merchant copes with it amusingly, but it set an uncomfortable tone for the rest of the interview, which becomes fractious by the end after Herring is unnecessarily rude about Extras. Usually Herring’s willingness to criticise, or at least question, his interviewees’ less lauded work is one of the best things about the show. On this occasion, it strayed into churlishness.

Aside from Merchant, the interviews are always good natured and very funny. In the Les Dennis interview, the Family Fortunes presenter talks movingly about the early death of his double-act partner Dustin Gee. Then, after a pause in which you think the interview might veer into grief porn, Herring perfectly breaks the sombre mood by saying “I wish my double-act partner had died”. It’s a moment that provokes uncontrollable laughter from Dennis and the audience alike. Similar paroxysms of delight occur often in his interviews with Greg Davies. One such moment happens after Davies tells a particularly ripe story about the day he skived off work as a teacher and while smugly sitting in his underwear on a velour sofa cocked his leg and “filled my pants full of shit”.

What sets RHLSTP apart from the likes of Graham Norton or Jonathan Ross is the luxury of interviewing just one guest for an hour or more. That time is something you simply don’t get on modern chatshows so, as entertaining as they can be, the conversation rarely touches on anything deeper than whether the guest gets recognised in Tesco. Stephen Fry’s suicide admission simply would not have happened on Graham Norton.

In that sense, Herring is a much-needed throwback to people like Michael Parkinson who, at least in the early days, was afforded plenty of time with each of his guests. Perhaps Herring’s next celebrity should be the great Yorkshireman himself. Let’s face it, who wouldn’t want to hear about his forward curl.