SNL writer isn’t afraid to make audiences laugh … and squirm

Advertisement

Advertise with us

Calling from a North Carolina airport in a voice just above a whisper, Maddie Wiener sounds more like a thoughtful friend than a comedian whose act includes jokes about sex, depression, body image and questionable behaviour.

Read this article for free:

or

Already have an account? Log in here »

To continue reading, please subscribe:

Subscribe and receive a limited-edition Free Press branded hat or tote.

Digital Subscription

One year of digital access for only $205*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles

*First annual payment billed as $205.00 + GST for one year. This annual subscription will automatically renew at $233.00 + GST every 52 weeks (10% off the regular annual price of $259.35). Offer available to new and qualified returning subscribers only. Cancel any time.

To continue reading, please subscribe:

Add Free Press access to your Brandon Sun subscription for only an additional

$1 for the first 4 weeks*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles
Start now

*Your next Brandon Sun subscription payment will increase by $1.00 and you will be charged $17.95 plus GST for four weeks. After four weeks, your payment will increase to $24.95 plus GST every four weeks.

Calling from a North Carolina airport in a voice just above a whisper, Maddie Wiener sounds more like a thoughtful friend than a comedian whose act includes jokes about sex, depression, body image and questionable behaviour.

Beneath the soft-spoken delivery is a comedian who delights in making audiences squirm.

Whether onstage, in the writers’ room at Saturday Night Live or behind the microphone as co-host of the We’re Having Gay Sex podcast, Wiener has built a following by taking audiences to uncomfortable places and finding the laughs in what most people would rather leave unsaid.

Supplied
                                Maddie Wiener has learned to love taking the audience to uncomfortable places.

Supplied

Maddie Wiener has learned to love taking the audience to uncomfortable places.

“I do love a laugh that’s also a groan. Like, ‘Oh, I didn’t want to laugh at that, but that got me.’ That’s kind of my favourite button to push,” says Wiener, who makes her Rumor’s Comedy Club debut from today to Saturday.

She isn’t interested in easy punchlines. Much of her material starts with questions she’s asking herself, awkward truths she’d rather not admit, or thoughts most people would rather not expose for all to see — or laugh at.

“When it’s something where you’re like, ‘Oh, I actually am embarrassed to admit that,’ there’s usually something really funny on the other side of it,” she says.

That sort of self-examination runs through almost everything she talks about. During a conversation that bounces from free speech and comedy to Alzheimer’s, sexism and pet rabbits, Wiener seems to genuinely enjoy pulling apart ideas to see what makes things tick.

“I like thinking about stuff,” she says. “Human consciousness is this thing that happened to me.”

It’s not exactly the answer you’d expect from someone who spends her nights offering up self-deprecation as a means to make strangers laugh.

Growing up, Wiener wasn’t the class clown. She describes herself as a straight-A student, a teacher’s pet and a dedicated rule-follower.

Then she discovered standup at 16.

“I thought it was the greatest thing ever.”

Part of that attraction, she says, came from finally finding a place where talking too much was encouraged. She credits her father with helping shape the way she sees the world. He encouraged her to question authority and challenge assumptions rather than simply accept them.

“It wasn’t disrespectful to question authority,” she says. “I think it’s made me an adult who values questioning things.”

That instinct shows up everywhere in her comedy. Rather than telling long personal stories, Wiener says she’s more interested in exploring ideas and observations, which can sometimes come from difficult places.

Part of her current set focuses on her father’s Alzheimer’s diagnosis, a topic she discusses with his permission.

“It’s obviously been a hard experience,” she says. “But we’ve been laughing a lot about it.”

She recalls an older comic telling younger performers there are no bad experiences in comedy because anything can become material.

“The worst thing in your life can happen and you’re like, ‘Well, I have this other thing that I can turn it into,’” she says. “It’s a really fun way to metabolize the world.”

Wiener is also candid about being a woman in standup. She says audience members have told her they expected less from her onstage.

“’You were actually really funny,’” she recalls being told. “I don’t think that’s a compliment. I mean, I’m glad I could win you over.”

At Rumor’s, she promises a mix of material ranging from pet rabbits to depression and suicide. The combination can sound jarring on paper, but the goal isn’t shock value.

“You can expect dark, you can expect weird,” she says. “But hopefully in a way that brings everyone on board.”

fparts@freepress.mb.ca

Report Error Submit a Tip

More Stories

Mosque’s restorative justice program helps newcomers find their way

Josiah Neufeld 10 minute read Preview

Mosque’s restorative justice program helps newcomers find their way

Josiah Neufeld 10 minute read Yesterday at 10:13 AM CDT

The Masjid Bilal is a chunky grey building just off Logan Avenue surrounded by warehouses and railyards. It looks more like a bunker than a mosque.

But on a summer Friday afternoon, its green-and-white carpeted interior is humming with activity. Two men in white robes and flat woolen caps are seated on the carpet poring over a copy of the Qur’an. A few young boys dodge through hallways, poking curious noses into open doors. At the back, next to a table piled with prayer mats, two girls in hijabs share schoolyard gossip. In the kitchen, women are cooking up pots of rice and chicken for people who will soon arrive for Friday prayers.

The Masjid Bilal is a community hub for members of Winnipeg’s African diaspora as well as Muslims from many other countries.

It’s also home to the Bilal Community and Family Centre, an innovative, community-centred nonprofit that is meeting vital needs for newcomers in this city.

Read
Yesterday at 10:13 AM CDT

WestJet adding two new direct flights from Winnipeg to warm-weather destinations

Aaron Epp 2 minute read Preview

WestJet adding two new direct flights from Winnipeg to warm-weather destinations

Aaron Epp 2 minute read 9:28 AM CDT

WestJet will launch direct flights to two more warm destinations this winter.

On Monday, the Alberta-based airline announced a direct route between Winnipeg and Punta Cana, Dominican Republic, and a direct route between Winnipeg and Belize City, Belize.

Each will be offered once a week, starting on Nov. 28 and Dec. 14, respectively.

The additions support the growing demand for options to warm weather destinations, John Weatherill, executive vice-president and chief commercial officer of WestJet, said in a news release Monday.

Read
9:28 AM CDT

Letters, July 20

6 minute read Preview

Letters, July 20

6 minute read 2:01 AM CDT

Erna Buffie’s recent commentary was a breath of fresh air and a much-needed reality check for our city’s leadership. I strongly support her assertion that true public service requires prioritizing people, communities and the environment over an outdated, debt-fuelled model of endless expansion.

Read
2:01 AM CDT

Puzzles Palace

1 minute read Monday, Jul. 13, 2026

To solve our puzzles, please subscribe with this special offer: |

‘Heartbreaking loss’: Sandy Bay First Nation offers condolences after apparent dog attack

Morgan Modjeski 3 minute read Preview

‘Heartbreaking loss’: Sandy Bay First Nation offers condolences after apparent dog attack

Morgan Modjeski 3 minute read Yesterday at 12:52 PM CDT

Leaders with the Sandy Bay Ojibway First Nation are offering their condolences after an animal rescue worker died following an apparent dog attack in the community and say the “stray and aggressive” animals are a longstanding issue.

Amanda Nobiss, 37, was volunteering in the community on the shores of Lake Manitoba with K9 Advocacy. Her remains were discovered on Friday morning.

The Manitoba First Nations Police Service said in a news release that it had been contacted by a friend of Amanda’s who was trying to locate her, around 12:45 a.m.

Using her cellphone location, police determined she appeared to be in Sandy Bay, said the release. Resources were dispatched to the area, including a drone, but due to the large radius of the cellphone “ping,” no one was located until 6 a.m.

Read
Yesterday at 12:52 PM CDT

A team — and league — of our own

Editorial 4 minute read Preview

A team — and league — of our own

Editorial 4 minute read 2:01 AM CDT

North American interest in soccer is at an all-time high. No wonder, given that Canada, Mexico and the United States have hosted the men’s World Cup for the past seven weeks.

Read
2:01 AM CDT