The debate over offensive comedy might feel as though it's been raging forever, but one person stands way out on the extreme fringes of that discussion. From quips about the then-imprisoned Nelson Mandela ('a cunt') to the entire Canadian population ('moosefuckers') and the missing Madeleine McCann (no, we're not printing any of that stuff here, sorry), Jerry Sadowitz has pulled not a single punch in his decades of stand-up gore.

As if to soften the outrage for those meek-mannered liberals among us, the oft-repeated suggestion is made that there's no greater target for his material than himself. Certainly, in interviews and onstage, Sadowitz emanates a deep self-loathing and appears brimful of regrets; in a 2011 Guardian interview, he bemoaned his 'completely wasted life'. His ire is particularly aimed at those he views as pretenders (Jimmy Carr, Ricky Gervais and Frankie Boyle are continually namechecked in this regard) who have romped off with all the glory and recognition that should rightfully have been his.

But he does have one skill that none of the above can wield: the ability to throw an amazing sleight-of-hand card trick into the mix, almost as a means of temporarily leavening the unfiltered degradation of his routines. There's no doubt that the New Jersey-born, Glasgow-raised Sadowitz is one of the most talented comics of his generation (everyone from Janey Godley to Richard Herring have touted him as a hero and influence). But you have to wonder just how far he might have gone had he been more inclined to play the game. In an age when stand-up and the internet have gone stratospheric in terms of both quality and quantity, Jerry Sadowitz remains comedy's version of the dark web.

King's Theatre, Edinburgh, Fri 23 Sep; Pavilion Theatre, Glasgow, Fri 30 Sep.