The RIFF Toronto

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Unearthing How Creatives Go from Good to Great. Toronto’s Creatives. We feed ’em. They talk. The hosts and guests never know what we’ll serve from Toronto’s world-renowned culinary scene. A my-toronto Show and PodcastHosted by internationally acclaimed Toronto artists: Visual Artist Gary O’Brien and Jazz Fusion Guitarist Jeremy Green.   From the comedy clubs of the core to the music venues of the west end, to Juno Award winners and Michelin-rated artists, The Riff is a chill hang with today’s inspiring artists in every form; on a mission to spark the creativity that lives inside everyone.

  1. Nov 4

    She Turned Bad Dates Into Billions of Views

    The RIFF S2 ep7 - Charlotte Dobre What happens when a classically trained actress, jazz vocalist, and one of YouTube's most authentic comedic voices sits down to talk about bad dates, embracing cringe, and turning pain into art? You get this episode of The Riff. Charlotte Dobre joins hosts Gary O'Brien and Jeremy Green to share her journey from being the weird kid with poop jokes to building a global audience of over 2.6 million subscribers and billions of views on YouTube. She opens up about her classical theater training at the University of Victoria, jazz vocal studies at the Victoria Conservatory of Music, and her time as lead host and writer for InformOverload — all of which shaped the unfiltered, genuine reaction style that made her channel a phenomenon. Charlotte dives deep into how she developed her comedic voice, the self-deprecation women in comedy still face, and why she believes the best comedy comes from truth and pain. She discusses the parasocial relationships with her audience, how social media algorithms reward negativity, and why she eventually had to step back from daily posting to protect her mental health. She also shares the story behind writing and self-funding her romantic comedy pilot Textuationships — inspired by her own Toronto dating disasters — which earned an official screening at the Toronto International Film Festival. Plus: setting boundaries in dating, how she met her husband, channeling negative energy into creativity, and why embracing the cringe is the key to making great art. If you enjoyed this conversation, hit that Like button, drop a comment with your favorite moment, and Subscribe to The Riff for more episodes exploring the creative thread that drives extraordinary people. Share this episode with someone who needs to hear that it's okay to be cringe. #CharlotteDobre #TheRiffPodcast #Comedy #YouTubeCreator #TorontoComedy #CreativeThread #EmbracingCringe #StandUpComedy #ContentCreation #PodcastInterview Resources Mentioned Charlotte Dobre's YouTube Channel: https://www.youtube.com/@CharlotteDobre Charlotte Dobre's Official Website: https://www.charlottedobre.net/ The Riff Podcast: https://my-toronto.ca/the-riff/ The Riff on Buzzsprout: https://theriff.buzzsprout.com/ mytoronto.ca (Show Sponsor): https://my-toronto.ca/ University of Victoria (BFA in Theatre): https://www.uvic.ca/ New York Film Academy: https://www.nyfa.edu/ Victoria Conservatory of Music: https://vcm.ca/ InformOverload (YouTube Channel): https://www.youtube.com/@InformOverload TIFF — Toronto International Film Festival: https://www.tiff.net/ Som Tum Jinda (Michelin-recommended Thai restaurant, 76 Gerrard St E, Toronto): https://somtumjinda.ca/ Isabella's Donuts (The Beaches, 2066 Queen St E, Toronto): https://isabellasdonuts.com/ YouTube Chapters 0:00 Pre-Show Banter: Horrible Dating Stories 0:47 Welcome to The Riff 1:42 Gary & Jeremy Catch Up 2:20 Gary's Electric Avenue Air Trumpet 3:29 Jeremy's Sex Machine Reaction 4:31 Introducing Charlotte Dobre 5:56 Charlotte's Missy Elliott Reaction 6:36 Childhood & Comedy Origins 8:15 Classical Theater & Jazz Training 9:29 Falling in Love With Jazz 10:45 Jazz Improvisation vs. Rehearsed Music 12:10 Comedy Influences: Lucille Ball & Carol Burnett 14:08 Relationship Comedy & Bad Dates 15:57 Dating for the Plot 17:33 Comedy, Pain & Truth 18:13 Calling Out Negative Behavior Online 19:56 Coping With Negative Stories 21:30 Social Media Algorithms & Negativity 22:37 Building a Relatable Audience 23:58 The Exhaustion of Being Authentic Online 25:36 Finding Comedy in Everyday Life 26:50 Channeling Pain Into Art 27:18 Humor as a Coping Mechanism 28:23 British Comedy & Dark Humor 29:01 Comedy Through Adversity 30:03 Charlotte's Own Bad Decisions 31:51 Setting Boundaries & Meeting Her Husband 33:01 Creating the Textuationships Pilot 36:53 Foodie Segment: Som Tum Jinda & Isabella's Donuts 40:53 The Creative Thread: Going From Good to Great 43:18 Embracing the Cringe 44:50 The Fear of Bombing 47:13 Where to Find Charlotte Dobre 48:02 Post-Interview Reflections Send us Fan Mail Support the show Want to watch this episode on YouTube? Subscribe to our YouTube channel

    She Turned Bad Dates Into Billions of Views

  2. Oct 21

    She Won an Oscar for Frankenstein - Here's What It Really Took

    The RIFF S2 ep.6 -Cliona Furey Final YouTube Description She won an Oscar for Frankenstein and has spent 15 years as Guillermo del Toro's go-to hair designer — and today she's telling us everything. On this episode of The Riff, Oscar and BAFTA-winning hair designer Cliona Fury (Crimson Peak, Nightmare Alley, Priscilla) joins hosts Gary and Jeremy for a candid conversation about building a career in film, working alongside legendary directors, and what it really takes to go from good to great. Cliona shares how she went from an opera house wig-making apprentice to one of the most in-demand hair designers in film, the discipline she learned from years in theater, and what it's really like on set with Guillermo del Toro — from his obsessive attention to detail to the code words his longtime crew uses to read his mind. She dives deep into her Oscar-winning work on Frankenstein, the meticulous historical research behind Priscilla, and the emotional toll and reward of owning your craft in a high-pressure industry. Plus, Gary shares a personal update on a hand-painted portrait of Rush drummer Neil Peart, and the crew heads to Union Station's German beer hall Wurst and Brazilian chocolate shop Chocolata Brigaderos for this episode's foodie segment, powered by MyToronto.ca. Whether you're an aspiring artist, film industry hopeful, or just love hearing how the movie magic really happens, this episode is packed with insight, honesty, and a few surprising stories from a career at the top of the industry. 👍 If you enjoyed this episode, give it a like, drop a comment with your favorite moment, subscribe for new episodes every week, and share it with someone who'd love it too. #TheRiffPodcast #ClionaFury #GuillermoDelToro #Frankenstein #HairAndMakeup #FilmIndustry #BehindTheScenes #TorontoPodcast #CreativeProcess #OscarWinner Resources Mentioned MyToronto: https://www.mytoronto.ca Wurst (Union Station / King St): https://wurstkitchen.com Zing Candy: https://www.zingcandy.com Netflix (Frankenstein behind-the-scenes special): https://www.netflix.com YouTube Chapters  0:00 Welcome to The Riff 0:48 Catching Up with Jeremy — Toto Concert Story 2:46 Gary's Neil Peart Portrait Reveal 5:04 Guest Introduction: Cliona Fury 6:13 Meet Cliona Fury 6:50 How Cliona Got Into Hair Design 7:53 Growing Up on Film Sets 14:13 Working with Guillermo del Toro 19:28 Behind the Scenes of Priscilla 26:28 Winning the Oscar for Frankenstein 33:13 Advice for Aspiring Artists 37:37 What's on the Table Today 39:04 Foodie Segment: Wurst & Chocolata Brigaderos 43:16 The Creative Thread: Good vs. Great 47:22 Thanking Cliona 49:00 Closing Thoughts Send us Fan Mail Support the show Want to watch this episode on YouTube? Subscribe to our YouTube channel

    She Won an Oscar for Frankenstein - Here's What It Really Took

  3. Oct 7

    Inside Hollywood’s Prop Workshop — Crafting Swords, Space Suits, Robots & Movie Magic

    Walter KlassenFX - The RIFF-S2 ep5 - Ever wonder how your favorite movies fake it — and make it look real? In this episode of The Riff, we sit down with Taku Desai, Chief Creative Officer of Walter Klassen FX — a Toronto-based special effects studio that's been behind the magic of Guillermo del Toro's Frankenstein, The Boys, The Handmaid's Tale, Captain America, Star Trek, Shazam, The Shape of Water, Reacher, and many more. We go inside the world of practical effects — how they build mechanical machine guns that don't fire, swords in five different materials for five different stunts, space helmets with hidden fans and magnetic battery covers, and animatronic animals so anatomically accurate you can't tell them from the real thing. Plus: Why are filmmakers ditching CGI and going back to practical effects? Is AI about to change everything again? And what does it take to build a career doing something this cool? We also talk Jack White's no-phones concert experience and why it felt like going back in time, Jeremy's jazz album In Motion hitting #1 on American radio, and we taste some incredible Nashville Hot Chicken from Chen Chen's at The Well in Toronto. 🎬 If you love film, behind-the-scenes magic, or the craft of making things with your hands — this one's for you. 📍 Walter Klassen FX: walterklassenfx (Instagram) | walterklassen.com 🎵 Jeremy Green – In Motion — out now - www.jeremygreenguitar.com Sponsored by mytoronto.ca — explore Toronto like a local. Subscribe, like, and hit the bell so you never miss an episode of The Riff. Send us Fan Mail Support the show Want to watch this episode on YouTube? Subscribe to our YouTube channel

    Inside Hollywood’s Prop Workshop — Crafting Swords, Space Suits, Robots & Movie Magic

  4. Sep 23

    Working With Major Artists: What Publicists See (Stories from the Road)

    The RIFF S2 - ep4 -Dawn Dwyer Pappas What is it actually like working with major artists behind the scenes? In this episode of The Riff, we sit down with an experienced music publicist who has worked at the highest levels of the industry. This conversation goes beyond theory and into real moments from the road, from press days to high-pressure situations where everything is on the line. These are grounded, human stories about supporting artists, managing energy, and helping things hold together when it matters most. We get into: • What working with top-level artists is really like day-to-day • How publicists support artists in high-pressure situations • The moments that don’t go as planned… and how they’re handled • What it takes to maintain momentum at a high level If you’ve ever wondered what happens around major artists when the spotlight isn’t on, this is a rare inside look. #MusicIndustry #Publicist #NSYNC #ChristinaAguilera #WWE #MusicBusiness #TorontoPodcast #BehindTheScenes #EntertainmentIndustry #PodcastClips Resources Mentioned WWE: https://www.wwe.com Sony Music Canada: https://www.sonymusic.ca BMG: https://www.bmg.com EMI/Universal Music Canada: https://www.universalmusic.ca Spotify: https://www.spotify.com myToronto.ca: https://www.mytoronto.ca YouTube Chapters 0:00 Cold open — the Christina Aguilera hotel story 1:10 Intro to The Riff Toronto 8:48 What does a music publicist actually do? 17:31 Life on the road with Christina Aguilera 21:20 Publicist vs. doing it yourself as an artist 26:36 Rule #1: never want it more than the artist 34:39 Behind the scenes at WWE 39:34 Ric Flair's book and other wild stories 46:05 The creative side of being a publicist 48:42 Food segment: Montreal bagels & Papa Roti coffee 58:43 Final thoughts and goodbye Send us Fan Mail Support the show Want to watch this episode on YouTube? Subscribe to our YouTube channel

    Working With Major Artists: What Publicists See (Stories from the Road)

  5. Sep 2

    From Uncle Trent's garage to iHeart's Top 40 Rock Charts

    Johnny Ross - The RIFF S2 ep3 Johnny Ross, frontman of Canadian rock band Learhaven, joins Gary and Jeremy on The Riff Toronto for one of our most honest and entertaining conversations yet. Johnny breaks down the wild chaos of touring Spain and Switzerland (burst pipes, gear crashes, and empty venues that filled up in 5 minutes flat), the story behind "Soulbreaker" landing on Hockey Night in Canada, and why his obsession with '70s tone, vintage gear, and vinyl isn't nostalgia — it's a philosophy. We get into the real talk: why comfort is the enemy of great art, what it actually takes to build a band that lasts, and the one thing Johnny says every great — from Zeppelin to Warren Buffett — has in common. Plus, Gary and Jeremy try Quan Quan on the Esplanade — a Vietnamese hidden gem with a 4.9 ⭐ Google rating that looks like a convenience store from the outside. 🎸 What's in this episode: 0:00 — Intro & the Rush T-shirt story10:00 — Johnny's origin story: Uncle Trent's garage, drums & the family instruments20:00 — Hockey goalie → rock frontman (the connection is real)30:00 — Building Learhaven, the writing process & vintage tone obsession33:00 — The European tour: burst pipes, gear crashes & packed venues45:00 — "Soulbreaker," vinyl, and the art of the album52:00 — What separates the greats? Johnny's answer: "artistic nicotine"🔗 Follow Johnny Ross & Learhaven: 🌐 Website: learhaven.com 📸 Instagram: @JohnnyRoss5th | @Learhaven 🎵 Stream "Soulbreaker" on all platforms 🌆 Toronto's best kept food secret: 📍 Quan Quan — 140 The Esplanade, Toronto 🌐 mytoronto.ca 🎙️ Follow The Riff Toronto: 📸 Instagram: @TheRiffToronto 🌐 mytoronto.ca If this episode fired you up, hit that subscribe button — it's how we keep landing guests like this. #TheRiff #JohnnyRoss #Learhaven #Soulbreaker #CanadianRock #TorontoMusic #RockPodcast #IndieRock #MusicPodcast #VinylCommunity #TorontoPodcast #HockeyNightInCanada #iHeartRadio #RockMusic #MusicianLife #BandLife #TorontoEats #QuanQuan #MyToronto #CreativeThread #RockAndRoll #PodcastLife #NewMusicAlert #LocalMusic #TorontoLocal Send us Fan Mail Support the show Want to watch this episode on YouTube? Subscribe to our YouTube channel

    From Uncle Trent's garage to iHeart's Top 40 Rock Charts

  6. Aug 5

    Why 99% of Content Creators Fail (And How He Didn't)

    Dontoverthinkitchip  - The RIFF S2 ep2 He quit a 6-figure insurance job with only $500/month coming in — and went $75K into debt chasing a dream. Three years later, he's landing brand deals with PlayStation, Nissan, the Toronto Blue Jays, and Chipotle, with 16 million views from nearly 6 million accounts. This is the story of @dontoverthinkitchip. In this episode of The Riff, Gary and Jeremy sit down with Toronto-based content creator Chip — the force behind one of Canada's fastest-rising social media channels. What started as a sports betting page in December 2023 has evolved into a full-time viral content machine built on relatable comedy skits, Toronto food culture, and one unbreakable rule: post every single day. In this episode: Why Chip walked away from a six-figure career with almost nothing in the bankThe real daily grind behind viral content (hint: it starts at 5:30 AM)How he sent 20 DMs a day to restaurants and turned $250 gigs into major brand contractsWhy your biggest supporters will never be the people you grew up withThe moment in Saskatchewan at minus 40 that almost broke him — and what kept him goingHow brands are now paying creators NOT to talk about their productWhy going viral overnight is actually less valuable than the slow grindThe Kevin James obsession that shaped his entire comedic styleWhat consistency + originality actually looks like in practiceWhy 99% of creators quit — and the one mindset shift that separates those who make itPlus: The guys taste pulled pork brisket mac & cheese from Smoke'N Bones on Baldwin Street — and Chip makes a case for why Baldwin Street is the most underrated food strip in Toronto. Whether you're a content creator, an entrepreneur, or just someone who's been sitting on a dream they haven't acted on yet — this one's for you. 🎙️ The Riff — where creativity winds its way through food, music, art, and everything in between. Hosted by Gary & Jeremy, brought to you from the heart of Toronto. 📍 Food feature sponsored by mytoronto.ca — your guide to exploring Toronto like a local. 🔔 Subscribe so you never miss an episode. Follow Chip: Instagram/TikTok/Facebook: @dontoverthinkitchip Follow The Riff: [Your social links here] Explore Toronto: mytoronto.ca --- #ContentCreator #Toronto #TheRiff #DontOverthinkItChip #TorontoFood #SocialMedia #CreatorEconomy #Entrepreneurship #SmokNBones #BaldwinStreet Send us Fan Mail Support the show Want to watch this episode on YouTube? Subscribe to our YouTube channel

    Why 99% of Content Creators Fail (And How He Didn't)

  7. Jul 14

    Electronic artist’s guide to playing big lineups

    Andrew Stasiw - The RIFF S2 ep1 Toronto's underground EDM scene has a new king — and he built it from a laptop during lockdown. Andrew Stasiw of King and Queen Events joins Gary and Jeremy on The Riff to pull back the curtain on how he went from bedroom producer to booking global heavyweights like Danny Avila, Maddox, and Sam Pacho at iconic venues like Coda — all as an independent operator competing against the monopolies. In this episode: 🎧 How to break into the EDM scene (basement to mainstage) 📈 The networking moves that actually work (cold emails are dead) 🌍 What it's REALLY like hosting international DJs in Toronto 🎶 Why reading the room separates good DJs from GREAT ones 💼 Balancing friendship and business in the music industry 🔥 Why Toronto's electronic scene is exploding RIGHT NOW Plus — we taste Rasta Pasta from Waterworks Food Hall. Jamaican-Italian fusion. Trust us on this one. Whether you're an aspiring DJ, a music lover, or an entrepreneur figuring out how to grind your way to the top — this episode hits different. Subscribe & hit the bell so you never miss a new episode of The Riff, where we chase the creative thread connecting music, food, arts, and culture. 🔗 King and Queen Events: kingqueenevents.com | @kingqueenevents ☕ Coffee by Found Coffee — Front Street, Toronto 🍝 Food by Rasta Pasta — Waterworks Food Hall, King West 🌐 Explore Toronto like a local: mytoronto.ca #TheRiff #TorontoEDM #KingQueenEvents #DJLife #TorontoNightlife #EDMToronto #Podcast #MusicBusiness #HouseMusic #Techno #AndrewStasiw #Coda #TorontoEvents Send us Fan Mail Support the show Want to watch this episode on YouTube? Subscribe to our YouTube channel

    Electronic artist’s guide to playing big lineups

  8. Jun 17

    200M Streams. No Label. No Rules.

    EMM - The Riff ep 12 She climbed into a coffin full of biting worms — and kept singing. 🎵🐛 In this episode of The Riff, Gary and Jeremy sit down with EMM — a classically trained, award-winning artist from Traverse City, Michigan who grew up surrounded by musical prodigies, moved to New York before high school, and built an independent music empire with 200 million streams entirely on her own terms. Now signed with Sony/The Orchard (while keeping full ownership of her masters), EMM is on The Dumb Tour promoting her album Black Diamond — and she stopped into The Riff studio fresh off a sold-out Toronto show at the Drake Underground. In this episode: 🎤 The coffin shoot — wrong worms, biting legs, 2 hours in bugs (and she was singing live) 🎹 Growing up at Interlochen, home of child prodigies practicing 12 hours a day 💡 Why "irrational confidence" is her secret weapon 💰 How brand deals funded her music before the music funded itself 🎧 The truth about publishing rights, predatory label contracts, and keeping your leverage 🌀 Manifestation, flow states, and "transcendence" on stage 📵 Dopamine detoxes and why boredom is rocket fuel for creativity 🍪 Gluten-free treats from Bunner's Bakery in Kensington Market (and yes, they're incredible) Whether you're an artist, entrepreneur, or just someone chasing something big — this one's for you. Follow EMM: @emminreallife (all socials) | Link in bio Explore Toronto like a local: mytoronto.ca 🔔 Like, subscribe & share — sharing is caring Send us Fan Mail Support the show Want to watch this episode on YouTube? Subscribe to our YouTube channel

    200M Streams. No Label. No Rules.
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About

Unearthing How Creatives Go from Good to Great. Toronto’s Creatives. We feed ’em. They talk. The hosts and guests never know what we’ll serve from Toronto’s world-renowned culinary scene. A my-toronto Show and PodcastHosted by internationally acclaimed Toronto artists: Visual Artist Gary O’Brien and Jazz Fusion Guitarist Jeremy Green.   From the comedy clubs of the core to the music venues of the west end, to Juno Award winners and Michelin-rated artists, The Riff is a chill hang with today’s inspiring artists in every form; on a mission to spark the creativity that lives inside everyone.

Information

  • Creator
    my-toronto.ca
  • Years Active
    2025 - 2026
  • Episodes
    19
  • Rating
    Explicit
  • Copyright
    © 2026 The RIFF Toronto
  • Show Website
    The RIFF Toronto

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