First impressions count, whether you are Jon Culshaw, on a date, or doing a stand-up comedy gig.  I've heard it said that a famous comedian has about two minutes grace to make an audience like them, while for newbies the stay of execution lasts a brutal 30 seconds. I've rarely seen this confirmed as much as last night at the 99 Club in Leicester Square during Alfie Brown's set.

As soon as Brown walked on I had a sense that things were not going to go well. Just as he was about to deliver his opening line the woman in front of me appeared to take a drinks order from her chum and got up and walked to the bar. Brown caught a glimpse of this and made a quick unscripted quip about it, but not a particularly funny one. 

Immediately the momentum was diminished. The fourth wall was broken, the dynamic had shifted and the audience – who had been pretty polite during the previous act – felt that they were allowed to pipe up. Someone at the back spotted Brown's luscious locks and trimmed beard and shouted out the rather unimaginative heckle "Russell Brand", to which Brown responded with something sarcastic on the lines of "you won't see him here, you have to be funny to appear in a comedy club".

From that moment, dissing a fellow comic, it felt as if Brown had lost the audience. The next fifteen minutes was excruciatingly watchable and bum-tighteningly awkward. Slo-mo car crash time. It did not help that Brown's material is probably too sophisticated for a Friday night up-for-a-giggle Leicester Square crowd that included a boisterous hen night party sporting red frilly stetsons. But actually the hen party – the wedding had been postponed, apparently, but that's a story for a blog on bizarre punters – was quite well-behaved. It was others in the audience who objected to Brown's routines, which could be described as having a complex post-post-post-feminist angle/agenda. 

Let's just say that this was not your normal Friday night comedy club patter. A riff about Shakespeare and profane language produced few chuckles. And when Brown attempted a discourse on the innate sexism in modern culture and the tyranny of body fascism, arguing, for instance, that men would still happily have sex with women if they all stopped wearing make-up overnight, the female members of the audience just heard the bits about men having sex with women and found his remarks annoying.

The trouble was that it was not just the odd noisy, well-lubricated heckler shouting "tell us a joke". Brown had divided the entire room. He lost the audience when talking about his girlfriend's periods then nearly won the sceptics back with a quick Michael McIntyre impression. But then lost them again with a sour remark about wanting to be on television which was meant ironically. Then he won them back with a neat comparison between the backchat at his gig and the things that occur at a Chris Rock show, but then lost them again. 

Afterwards Brown tweeted that "gigs like that are always the most fun". From where I was sitting it looked more like a learning experience than fun. I'm sure on other nights, with a following wind, a sympathetic ear and a good opening Brown would do very well. There is no faulting his intellectual ambition, he just didn't have the comedic artillery to back himself up and make everyone laugh tonight. In fact it was funny that someone shouted "Russell Brand" because that was who Brown reminded me of. Not because of the hair and the facial topiary, but because he was prepared to be painfully honest and go into areas where comedians prefer not to go (and I'm not talking about Leicester Square on a Friday evening). 

For me, however, Brown's fate was sealed when he lost the crowd within 30 seconds of walking onstage. I'm sure he has had better gigs in the past and I'm sure he will have better gigs in the future. But he needs to remember that making that good first impression really matters. In fact he should know all about impressions already. It should even be in his genes. When I was researching this piece I found out that his mum is impressionist Jan Ravens. 

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