Over the course of his 15-plus years on stage in his native Australia, the United Kingdom, and, now, here in the states, Jim Jefferies hasn’t shied away from speaking his mind (usually with humorous results). As the acerbic Aussie’s material developed and became exceedingly more vicious, his star as a stand-up only grew. With increased notoriety came increased scrutiny from the ever-growing audience aware of his fearless and deliberately offensive material, which only found Jefferies railing even harder against even more controversial issues and sects of society on stage. By the time the controversial comic took some verbal swings at gun enthusiasts and card-carrying feminists in his latest special (last year’s Bare), Jefferies’ pointed brand of stand-up was sustaining itself: Say something outlandish, watch the waves of outrage roll in, say even more outrageous things in next special in response to that outrage, repeat.

Saturday night was a continuation of the process, as nobody was safe from Jefferies’ functionally-hilarious ire and unique low-brow poignancy—whether they were gun owners, women, vaccination opponents, Bill Cosby, America, or even his own fans—as the comic pushed boundaries for two hour and managed to still leave Pabst Theater laughing.

Coming out to a roaring applause from what turned out to be a particularly out-of-control crowd (more on that later), Jefferies—holding his first of two on-stage cocktails and crammed into a shiny silver jacket he’d later reveal Ringo Starr convinced him to buy—came out swinging by bypassing allegations and flat out calling Bill Cosby a rapist. Having appeared in Canada days after a Cosby appearance, he was shocked to learn that two thirds of ticket holders for the sold out Cosby show still came. Meanwhile, Jefferies’ hate mail for doing said Cosby material was piling up. “These people would rather watch a clean comic who rapes than a dirty comic who has only raped a few times,” he quipped, as the Australian accent served to soften the blow.

Tone effectively set, he went down the ever-growing list of things people were angry at him for saying, including rants (complete with pantomimed masturbation) against gun-owners and people quick to cry misogyny. “If you feel you’ve learned anything this evening, it’s accidental,” he said, punctuating his regularly-repeated “These are just jokes!” message. As the set progressed and the level of his pint of booze reduced, Jefferies’ material narrowed from broad issues into more personal paths to laughter. After a tirade against anti-immunization groups, he revealed that he’d recently found out he was autistic. In one of his many bits about his two-year-old son, Jefferies discussed potty training, with a graphic (and fictional) lesson on how to handle hemorrhoids. He expressed his hopes his son would grow up to be handsome, explaining how much Jefferies (a self-proclaimed five on the scale of attractiveness) would prefer to be attractive than smart. “To be the best looking man on the planet, I’d go full retard,” he offered, before making the types of sounds and mannerisms that surely inspired emails that will soon inspire more material.

As the show wound down, Jefferies assured the increasingly outspoken audience he loved the USA, then proceeded to comment on Americans’ tendency to tout freedom—though “Not even in the top 10 of freest places—and value heritage from countries we’d never visited (with “Mick” and “Guido” jabs spliced in to hammer the point home). With the two-hour mark approaching, a member of the audience (which, as  whole, Jefferies had chided earlier for getting up too often and for phone use) screamed the inaudible utterance that finally proved to be enough for the headliner. “At what moment in your little fucking head did you think, ‘Jim’s struggling, maybe I should yell out some inane bullshit.’?” he scolded, likely set off by the previous 100-plus of audience behavior minutes as well. Unfortunately, the acknowledgment only prompted more outbursts. As another guy’s continual request for the “April 18th” bit, Jefferies responded, “I feel your life would be much better off if you stayed home and watched one of my DVDs instead.” Then some guy slurred something about wanting a radish, to which the comedian couldn’t even will himself to muster a response.

Though disjointed at times and (based on the collective patience of the talkative audience) about 20 minutes too long, Jefferies’ freewheeling and fearless set went brazenly down some taboo avenues of society and, more often than not, wound up leading to laughs.