Playing out at times like an extended monologue by the floppy-haired, bespectacled one in your anxiety therapy group, Simon Amstell’s stand-up is at times painfully honest, poignantly perceptive and wryly self-aware.

Simon Amstell’s rise from pop-culture pundit, casually cutting down any hapless celebrity who he confronts, to stand-up “artiste” craving to be taken more seriously, may warrant thankless comparisons to his friend and peer Russell Brand. However, Amstell presents himself as much more of a dedicated student of the craft. Peering through his thick-rimmed glasses and whimsy-fringe, analysing his crowd and calculating when to deliver the sting in whatever self-deprecating story he is recounting, there is a cool precision to his words. His slow, poised, ballerina-like amble onto the Northcott Theatre’s stage is that of a philosophy professor, rather than the “performing clown” he purports to be.

It’s this craftsmanship which elevates his scrupulous self-scrutiny from the late-night ramblings of some humourless undergrad having just read Kant, to something far more intimate and hilarious.

An anecdote about a trip to France with his current boyfriend, during which he spends time fantasising about a well-lubricated young man in a sex dungeon, exemplified his ability to unearth the most absurd inner thoughts and turn them into relatable (who hasn’t fantasised about a lubed-up dungeon boy?) internal conflicts of desire and logic, of the unconscious and the conscious. He has stripped down comedy to its most basic functions and, in the process, highlighting the disjunction between what we think we think and what we really think. I think.

Like Brand, however, Amstell can occasionally drift into a level of narcissistic self-awareness which risks isolation from the crowd. By dissecting the moment he made a “controversial” comment on Radio 1, in which he compared the station’s racial separation from the predominantly black-hosted 1extra on the day of Nelson Mandela’s death, Amstell risked alienating the audience, mutating what was initially intimate confessions into what felt more like readings from masturbatory memoirs. That isn’t to say Mr. Amstell isn’t aware of this, though.

His ego is an essential character in his stand-up, a constant antagonist who threatens to derail our vulnerable, fame-stricken protagonist. Like some schizophrenic cat-and-mouse chase, the audience is constantly hoping that the humble persona will eventually succeed, yet it’s impossible to deny the ludicrous enjoyment of hearing a scrawny, awkward young man believe that, even if just for a moment, he was God.

To Be Free is a natural sequel to his debut tour, Numb, illustrating the comedian’s evolution from confessing his crippling insecurities and inability to “live in the moment”, to wrestling with his own egomania in the wake of becoming a more credible celebrity; arguably an artist. Leaving the audience with his pseudo-Buddhist reflection that to be free of the ego is to find truth, Simon naturally applies this to an autistic child masturbating on a bus, outlining that in our self-aware culture, seriousness requires the ridiculous, and vice versa.