Phil Nichol, Soho Theatre

How far is too far? That’s the question which underlies the nihilistic versifying of Bobby Spade, white-suited barfly bard, the laureate of oedipal self-loathing who swims in a miasma of misogyny. Spade is the deeply strange, deeply funny creation of Phil Nichol. In this show the no doubt decent Nichol doesn’t get a look in. Where Rich Hall brings on his alter-ego Otis Lee Crenshaw in the second half, Nichol comes on as Spade and goes off as Spade. And, boy, does he go off.

It’s hard to credit that Spade bubbled up in the head of a Canadian comedian. Without wishing to stereotype, you expect something a little more sweet-natured from that quarter. Before two minutes were up Bobby Spade had told a series of defiant jokes about deafness, blindness and Parkinson’s. He took some getting used to. His first grim-faced recitation was greeted with bewildered silence, evidently anticipated.  “Don't spoil it with applause!” he commanded. As the performance wore on, it became necessary to disobey.

You don't need to have spent your nights being harangued in smokey clubs by jazz-backed beat poets spouting doom-laden worldviews to appreciate the subtleties, such as they were, of this startling parodic creation. Nichol evidently has a dark side which he puts into the mouth of a character who, being manifestly dysfunctional, can get away with it. Jimmy Carr does it, argued Spade as he trampled another taboo underfoot. In his pristine two-piece, episcopal shirt and carefully slicked mop he even looked a little like Carr’s demented doppelganger.

Unlike Carr, Spade sings, like a deranged Baptist preacher, possibly possessed and speaking in tongues. His songs and rhymes are unremittingly dyspeptic messages from the front line of misery and hate. “Life is grim,” proclaims one. “You can’t say that to me” screams another. He concluded with a song which enshrined the only logical response to an hour of gazing into the abyss of his own navel. Its title: “Kill Yourself”.

But not before doing damage to others. Although he claims to hate both sexes equally – in a typically adroit play on words, he’s “bi-furious” - Spade is mostly fixated on mining his catastrophic relationship with women. Naturally it all goes back to the mother who, in one free verse paean, he claims to have dispatched. Then there are the wives. He’s been married four times, divorced once, leaving open the question of how the others exited the contract. We discovered that they were all reliably unfaithful. Spade told a series of boiler-plate jokes – why did the chicken cross the road?/knock knock etc – and each time the answer led back to marital betrayal. Hilarious. One song was called “Helen Keller’s Fella”. A poem referred to Snow White’s nether topiary arrangements. “You have the most boobs” was the smoothest compliment in his locker. The only people Spade seems inclined to look up to got their own song, “Haemophiliac Albino Cowboys”, which is of course a hedge-betting exercise in scattergun offence. Spade is an expert at that.

It’s not quite true to say that Nichol is unseen in all of this. Declaiming Spade’s lyrics in rapid-fire bursts from a crumpled cribsheet, he sometimes mangled the punchline and, edging out of character, would even admit it. So how far is too far? One song got a little bit too fallopian for my taste. But others in the room carried on rocking with laughter, and not all of them sad lonely women-hating losers. Maybe even none of them.

• Phil Nichol continues at the Soho Theatre until 13 March. Book online.

Watch a clip of Phil Nichol performing as Bobby Spade at the Edinburgh Festival in 2009: