According to the Guardian's Edward Tew, Richard Herring is "not-so-quietly becoming the best celebrity interviewer in the land". A bold claim, to be sure, but one that I think holds some truth.
As Tew explains, the combination of puerile questioning and light-hearted disrespect that Herring adopts towards guests on his Leicester Square Theatre Podcast almost invariably succeeds in prompting hilarious anecdotes, fascinating conversations and sometimes even candid confessions. The episodes are often long and freeform, lacking much in the way of even organic structure - but then the duration of the interviews and the absence of talk show convention/niceties are precisely what make them so refreshingly different.
Of course, such an approach means that (in Herring's own words) it's "a very fine balancing act" and there are occasional moments of friction and awkwardness between interviewer and interviewee. In this regard, the episode with Stephen Merchant is unsurprisingly cited by Tew (though Herring has since suggested that the journalist is wide of the mark in his account of the source of Merchant's displeasure).
More often than not, though, the guests quickly acclimatise to the situation and are happy to go with the flow - and the result is superb entertainment. I can't recommend the episodes with Stephen Fry, Stewart Lee, Adam Buxton, Greg Davies and Bob Mortimer highly enough - but, to be honest, they're all worth a watch/listen.