Remember the first time you ate an olive? You bit down and the salt hit your tongue. It felt like the whole ocean was slapping you in the face. You spat it out and yelled at whoever gave you the thing. ‘How the FUCK could anyone enjoy those?!’ you asked. A good question. But slowly, over time, your palate ’matured’, and you became addicted to the tang. Greg Proops’ podcast is like an olive. It’s sharp, insulting, disorganised and inconsistent. And it’s marvellous.

You may know Greg from Whose Line is it Anyway?. He’s the curly haired one with glasses. He describes his role on the show as supporting, next to two of the greatest improvisational minds of his time: Ryan Stiles and Colin Mocharie. But Greg does himself a disservice, proving on his podcast alone that the sharpness of his unplanned wit is comparable to Oscar Wilde with claws. Greg’s had an admirable and successful career, (including, surprisingly, voicing Bob the Builder for four seasons), and now trots around the world working extremely hard at being a fine stand up comedian.

But part of Greg’s initial saltiness is his inability to fit into any comedian’s paradigm that has come before him. He’s not interested in landing a sitcom. Not even a funky trendy one with HBO. In fact, Greg doesn’t particularly care what you fucking think. Take this argument with a heckler from his most recent podcast episode (they’re all live):

Oh no, I’m looking at you down the bar…no this isn’t a fucking cocktail lounge. There will be fucking silence in this room until I am finished tonight. You think I’m fucking kidding, I’m not fucking kidding. I’ll take the mic and I will walk down there and shove it up your ass like Alexander the fucking Great against the Persians. You will fucking taste my javelin here tonight. That’s how this fucking works. There are a thousand bars on this street. I invite you to FUCK OFF and go to one of them and be with your other douchebag dickhead drunk patty motherfucker friends, how’s that fucking grab you?

And the crowd goes wild. This is particularly vicious for Greg, but indicative of his underlying attitude. He’s pissed off at the world. But he manipulates his rage like a craftsmen. At times it’s hilarious and we’re laughing at him. At other times, it’s tragic. In his best moments, when he goes into his ‘boring preachy part’, he is capable of leading a revolution.

The premise of the podcast is beautifully vague. Titled ‘The Smartest Man in the World’, Greg performs live to a crowd every week for free. He has semi-prepared talking points, but for the most part it’s a 90 minute improvised one man show live every week. The sheer ballsy bravery of this is only matched by the fact that he almost always pulls it off. The title works off Greg’s schitck: a faux arrogance that seeps through his rage. Listeners send in questions and must adress him in some sort of imaginative salute: ‘Your Most Proop-full-ness’ etc. But Proops is actually fiercely intelligent, and delivers profound and intelligent stand up apparently off the cuff.

This is how he opened a recent show:

Hallelujah! Once again the Proopcast takes to the butterfly’s wings that are so extent all around Chicago. As we once more take to the ether on the wing’s of a butterfly here at the fabulous Zany’s on North Wells, Chicago’s oldest and grandest comedy club. We seek to connect with each and every one of you out there in Proopland, so if you’re listening now at the gym working that stair master this is an awesome time to pour yourself a drink from that little flask you brought with you. If you’re sitting at home, this is a great time to light one up. And if you’re at work, why don’t you take a break? For about an hour and twenty-five minutes.

He’s poetic, and drier than a fucking nun’s nasty. He often refers to the show as a ‘vodcast’, as is he is delivered vodka throughout the show by whatever bar he’s playing at. He is an enormous supporter of recreational cannabis use, and is possibly the best mascot for that campaign. His frequent taking of drugs has apparently done nothing to damage his work ethic or sharpness of wit. It’s here that the podcast draws its most easy criticism. Greg makes pot and drink look fucking cool.

That aside, this is a cool guy, and the podcast will teach you about cool. Greg will often talk on men’s fashion. He wears a collared shirt everywhere, and most often a suit. This, along with his sipping of vodka throughout the show, gives him a vintage cool that is reminiscent of a Mad Men era of masculinity. Greg’s other favourite topics include: funk music, old movies, Negro league baseball and European and American politics. These potentially alienating niche interests are filtered through genuine passion and humour that make you want to learn more. I didn’t know who Satchel Paige was before listening to this show. Now I do. He’s fucking amazing.

His best moments are his insights into politics and media. Greg taught me about the occupy movement in a genuine and meaningful way. And the International Monetary Fund. And the recent Frech elections. His frequent discourse on the war on women is awe-inspiring. He is one of the most sensible and accesible voices on contemporary feminism I’ve encountered, and in this way is the very model of an honourable man. Because of him I want to know more and act more in making the world a better place. This from a ‘comedian’ who improvises a 90 minute show every week.

Greg’s comedy then is  a great marriage of past and present. There is so much about him that is of a different era: the suit, the drinking, the homage to a more Golden Age. The podcast itself feels at times like something from a great philosophical Greecian discourse or debate. The live format means there’s always a risk of something falling flat, but this happens so rarely. Greg slaps a crowd around and then leads them. It’s like Tristan Tzara, just slightly more organised. He enjoys ideas. And satire. And won’t stand fools. Yet his outlook is so forward, so progressive, that even in his cynicism he is filled with hope for the future. In 90 minutes, every week, Greg destroys the world and then builds it up again.

Oh, no! I haven’t lost hope at all! Look, we’re all here–we’re all having a good time on Sunday night! I just read you a lot of depressing shit like that and talk about these things because you have to think about them sometimes. I haven’t lost hope at all. There’s going to be abortion; there’s going to be health care; there’s going to be medical marijuana; there’s going to be peace in the world; there’s going to be homosexual marriage: all this is going to happen, because all the generation that hates it and is against it and is fervent about it is going to die. I may not get to see it, but . . . The people who are young right now don’t care about any of those things: they care about technology; they care about eating; they care about learning. They’re curious; they want to find out things; they want the world to be bigger; they want to know about other people in other places; they want to inform themselves and use analytical thinking; they don’t trust the traditional media sources that we’ve all been poisoned to fucking listen to like the television and the newspapers and all the shit that comes up on the Internet: they learn to fucking discern because they have to pick out pieces of information all the time. So, I have nothing but fucking hope for the world.

I would quote him more, but the thoughts are so tangential and disorganised that you really have to experience it for yourself. Stick with it for a couple of episodes. Like I said, Greg produces something so different to anything that’s out there that it can take a while to get your head around it. For that reason he should be celebrated. I desperately want to have a drink with him. Cheers.

Here’s the website and the link to iTunes.