They call Winnipeg the “Chicago of the North,” and it’s not just because of the architecture—it’s the killer comedy scene. This city punches way above its weight class when it comes to laughs.
Whether you’re planning a corporate gala, a wedding reception, or a charity fundraiser, bringing in a local pro changes the entire vibe. There is nothing quite like a room full of people bonding over shared Manitoba miseries and joys.
Finding the best comedians for hire in Winnipeg means looking for authentic, independent talent. We’ve curated this list based on pros who are easy to contact directly and have a proven track record of bringing the house down.
While many of these acts are fully independent, platforms like AGNT are also making it easier than ever to secure verified local entertainers safely.
The Top 10 Comedians for Hire in Winnipeg
Ready to bring down the house? We’ve scouted the local scene to find the funniest, most reliable, and truly independent talent available. These performers know exactly how to work a Winnipeg crowd and are ready to make your next event unforgettable.
Big Daddy Tazz (The Bi-Polar Buddha)
Big Daddy Tazz is a total legend around here. Known as the “Bi-Polar Buddha,” his show is a unique cocktail of belly laughs and mental health advocacy. He doesn’t just crack wise; he opens up about life’s struggles in a way that is hilarious and healing.
This makes him one of the most versatile comedians for hire in Winnipeg, especially for corporate wellness events or fundraisers where you want the entertainment to mean something.
- Focus: Mental health advocacy mixed with belly laughs.
- Best For: Corporate wellness events, fundraisers, and motivational comedy.
Matt Falk (Clean & Corporate Friendly)
If you are worried about HR calling you the next morning, Matt Falk is your guy. He has carved out a massive niche as one of the few truly “squeaky clean” comics who is actually hilarious.
His high-energy act is polished enough for big corporate stages and safe enough for church basements, without ever feeling watered down.
Matt has millions of views on his Dry Bar Comedy specials and has placed in the World Series of Comedy in Las Vegas. When people ask for recommendations on family-friendly comedians Winnipeg has to offer, Matt is almost always the first name on the list because he guarantees big laughs without the cringe factor.
- Focus: High-energy, clean comedy that is “99% HR approved.”
- Best For: Conservative corporate crowds, church groups, and all-ages events.
Dean Jenkinson (The Comedy Veteran)
Dean Jenkinson is the kind of comedian that other comedians stop to watch. He is incredibly sharp, clever, and brings a level of writing quality that you don’t see every day. That’s probably because he’s been a writer for This Hour Has 22 Minutes since 2007 and has penned material for major names like The Muppets and Joan Rivers.
If you need someone who can read a sophisticated room and deliver smart, witty material without relying on cheap tricks, Dean is your best bet.
He stands out among the top comedians Winnipeg has produced because he blends that prairie charm with world-class writing chops, making him perfect for high-stakes galas where the entertainment needs to be intelligent.
- Focus: Smart, writing-focused humor (writer for This Hour Has 22 Minutes).
- Best For: Professional associations, awards galas, and smart audiences.
Dan Verville (The Relatable Host)
Dan Verville is the kind of guy everyone feels like they already know. He’s a regular headliner at Rumor’s Comedy Club and has been featured on CBC Radio’s Laugh Out Loud, but his real superpower is his relatability. He takes everyday absurdities—like grocery shopping or turning into his father—and spins them into gold.
Because he is so naturally engaging and likable, Dan is a fantastic choice if you need a comedian Winnipeg locals will instantly connect with. He is also a top-tier emcee who can keep a festival or casual corporate party moving smoothly without ever letting the energy dip.
- Focus: Observational humor and excellent emcee skills.
- Best For: Hosting duties, festivals, and casual corporate parties.
Paul Rabliauskas (The TV Star)
You probably recognize Paul Rabliauskas from his smash-hit CTV sitcom, Acting Good, which he created and stars in. But before he was a TV star, he was grinding it out on stages across the country, perfecting his craft.
His comedy draws deeply from his experiences living on the Poplar River First Nation and navigating life in the city, delivered with a charm that is impossible to resist.
Booking Paul brings a level of star power that few others can match. His storytelling is masterful, his perspective is unique, and he is undeniably one of the best comedians that you can hire in Winnipeg if you want a headline act that will have your guests bragging about the event for months.
- Focus: Indigenous perspective, storytelling, and star power (creator of CTV’s Acting Good).
- Best For: Headline performances and events seeking a big name.
Dana Smith (The Sketch & Stand-Up Pro)
If your event leans a bit more creative or alternative, Dana Smith is a brilliant choice. As a member of the acclaimed sketch group HUNKS, she has performed at San Francisco Sketchfest and the Chicago Sketch Comedy Festival.
Her solo stand-up is just as impressive—smart, satirical, and often tackling topics that standard club comics miss.
She is perfect for arts festivals, progressive corporate functions, or any crowd that appreciates comedy with a bit more edge and intellect. When searching for unique comedians for hire in Winnipeg, Dana stands out because she brings that improv-honed quickness to every single set.
- Focus: Sketch comedy (member of the group HUNKS), stand-up, and satirical writing.
- Best For: Creative events, arts festivals, and audiences who enjoy smart, alternative comedy.
Chad Anderson (The Storyteller)
Chad Anderson doesn’t just tell jokes; he spins narratives that pull you in. Originally from The Pas and a proud Cree comedian, Chad’s style is disarmingly honest. He mines his own life for material—tackling heavy subjects like fatherhood, tragedy, and racism—and somehow makes them hilarious without losing their weight.
He has been featured on CBC’s The Debaters and released a fantastic album, Live at Wee Johnny’s. If you want a performer who connects on a deeper, more personal level while still delivering punchline after punchline, Chad is a fantastic addition to any lineup.
- Focus: Personal stories, fatherhood, and overcoming tragedy with humor.
- Best For: Comedy clubs, private parties, and resilient crowds.
Scott Porteous (The Comedy Dangerist)
Scott Porteous offers a two-for-one deal that you won’t find anywhere else. You can book him as Scott—a sharp, rapid-fire stand-up with nearly 20 years of experience—or as his alter-ego, Herbert Henries, the world’s only “Comedy Dangerist.”
Herbert is a character act that mixes awkward anti-comedy with “dangerous” stunts (that are usually more hilarious than life-threatening). He recently took this act to Canada’s Got Talent, earning praise from Howie Mandel.
If you are scouting for unique comedians for hire in Winnipeg who can offer a completely different experience for your guests, Scott is the wildcard you need.
- Focus: Versatile stand-up and character comedy (Herbert Henries).
- Best For: Clubs, festivals, and events wanting something unique.
Ben Walker (The Quick Wit)
Ben Walker is the master of the “quick wit.” As a regular host at Rumor’s Comedy Club and a three-time semi-finalist for SiriusXM’s Next Top Comic, he has honed a style that is fast, responsive, and incredibly engaging.
He doesn’t just recite a script; he reads the room and interacts with the crowd in a way that feels spontaneous and electric.
This makes him one of the most exciting comedians that you can book for events in Winnipeg, especially if you want an emcee who can handle hecklers (playfully) or keep the energy high during long awards ceremonies.
- Focus: Off-the-cuff humor and crowd engagement.
- Best For: Corporate events, fundraisers, and clubs.
Ryan Pilling (The Magic of Comedy)
Sometimes a microphone just isn’t enough. If you want interaction that gets the whole room involved, Ryan Pilling is a phenomenal choice. While he is based in Calgary, he is a frequent flyer to Winnipeg and a top-rated highlight on the AGNT platform.
His show is a high-energy blend of impressive magic and clean, sharp comedy that is perfect for corporate mixers or after-dinner entertainment.
He’s not just a guy doing card tricks; he’s an entertainer who makes your guests part of the act, ensuring the laughs are shared and the memories stick.
- Focus: A highlight from the AGNT platform. Although Calgary-based, he frequently services Winnipeg with a blend of magic and comedy.
- Best For: Interactive corporate events where you need more than just a microphone.
How to Hire a Comedian in Winnipeg (Buying Guide)
Booking talent doesn’t have to be a gamble. If you have never hired a stand-up comic before, here is what you need to know to ensure your event is a smashing success.
Budgeting: What to Expect in Terms of Cost
The cost of hiring a comedian in Winnipeg can vary significantly depending on their experience and “fame” level.
- Local Pros & Club Regulars: For a solid 30-45 minute set from a talented local pro (like many on this list), expect to budget between $700 and $1,500.
- Corporate Specialists: For experienced corporate acts who specialize in clean, tailored material (like Matt Falk or Big Daddy Tazz), fees often range from $1,500 to $5,000+.
- TV Stars: If you are looking for a nationally recognized name (like Paul Rabliauskas), you are likely looking at $5,000 to $10,000+, plus travel riders if they are touring.
Always ask if travel and accommodation are included in the quote, especially if you are bringing in talent from outside the city perimeter.
Vetting: Checking Videos and Reviews
Never book a comedian sight unseen.
- Watch Recent Clips: Ask for a video from the last 12 months. Comedy styles evolve, and you want to make sure their current material matches your event’s vibe.
- Check “Corporate” References: Being funny in a dark club is different than being funny at a brightly lit corporate luncheon. Ask for testimonials specifically from previous corporate clients to ensure they can handle a professional environment.
- Read the Room: If your event is for a church group or a conservative industry, verify their “clean” credentials. A “clean” set means no swearing and no controversial topics—make sure you and the comic have the same definition of “clean.”
Contracts: Why Platforms Like AGNT or Direct Contracts Matter
Handshakes are great, but contracts save friendships (and events).
- Direct Booking: Many of the independent comedians for hire in Winnipeg listed above can be booked directly through their websites. This often saves you agency fees, but it means you are responsible for handling the contract and deposit yourself.
- Booking Platforms: Using a platform like AGNT adds a layer of security. They vet the talent for you, handle the payments securely (so you aren’t e-transferring a stranger), and provide a standardized contract that protects both you and the performer. If a comedian cancels last minute, a platform can often help you find a replacement faster than you could on your own.
Conclusion
Winnipeg isn’t just cold; it’s cool, thanks to a comedy scene that rivals any major city. From the mental health advocacy of Big Daddy Tazz to the sharp wit of Ben Walker and the magic of Ryan Pilling, this city offers a performer for every possible vibe. Whether you need squeaky-clean corporate humor or an edgy club set, the local talent pool runs deep.
Supporting these independent artists not only guarantees a killer event but also keeps the local arts community thriving. If you are ready to book one of the best comedians for hire in Winnipeg, reach out to them directly or browse AGNT for a seamless, secure booking experience. Your guests—and your stress levels—will thank you.
Also check our article: Best Magicians for Hire in Winnipeg for Private Events
