Thanks to Nic’s internet-fu we heard about Dave Chappelle’s three pop-up shows being staged at the Winter Garden Theatre this week, and were able to snag some tickets before it quickly sold out. Given that it’d been almost six years since the reclusive stand-up comedian had performed in Toronto after quitting his cable show, really not all that surprising. Accompanied by DJ Future the Prince (Drake’s official deejay) the crowd was entertained with his beats as the theatre filed in for the performance, before the opening comic Gilson Lubin came out and did a great job warming up the crowd with a routine strongly peppered with jokes from around Toronto and references to the TTC.

Due to complaints however from the city about his Monday show were he smoked on stage, Dave Chappelle was not allowed to do so Tuesday night, which might have contributed to some of the clunkiness with his transitions as he clearly seemed to be jonesing for a cigarette. Amusingly this did provoke a joint being thrown on stage by a member of the audience, followed by some sort of pipe and a cigarette lighter. As you can imagine there was a lot of interest in seeming him actually smoke the proffered drugs, but would never be realized as he made jokes about him being jailed later that night strung out on the PCP which no doubt laced the joint.

This however did inform some of his opening routine with some commentary on Canadian policies/politics, but also how Canada really needs to start a war so the rest of the world takes our flag seriously. And while there was a lot of vintage Chappelle throughout the show, there certainly has been a change in tone with his material as he now talks more about getting old, and not being to go out like he used to, but has also incorporated his quitting the Dave Chappelle Show and the tabloid headlines and paparazzi that follow him and his family now into the routine.

Beyond tales of his trials and tribulations in show business, his material also touched upon his travels across the United States, American politics, and plenty more. However it does appear that he’s still working out the kinks, and while a really good show, did meander at times, or just petered out as he moved with the comedic flow. Confessing that he didn’t have a big finish yet, he thanked the crowd sincerely for their support and walked out to one of his favourite Jay-Z songs.

Overall it was an entertaining night that literally left you crying tears. Anyone who’s lucky enough to make it out to the last show tonight should not be disappointed.