“I thought you would be terrible but you weren’t.”

Rollin Penner is a sharp, observational stand-up whose dry wit and fearless honesty turn mundane events into laugh-out-loud moments. Rollin mines relationships, modern culture, religion, technology and a host of other subjects for his material, which he delivers with a disarmingly casual stage presence that sometimes belies the dark truths hidden inside the jokes.

A confident storyteller and master of timing, Rollin balances his fearless humor with surprising warmth, and his relentless honesty with unexpected kindness. And his killer punchlines will stay with audiences long after the lights go up.

Rollin is a seasoned performer equally comfortable as a host, feature or headliner. His credits include:

-over 300 comedy sketches written and performed on CBC Radio

-over 200 comic stories published in newspapers including the Winnipeg Free Press

-numerous appearances at The Winnipeg Comedy Festival

-regular host, feature and headliner for Yuk Yuks Comedy Clubs

-Headliner at Rumors Comedy Club

-Headliner at numerous private and Corporate events across Manitoba and Ontario

Don’t let his well dressed grandfatherly appearance fool you! Rollin Penner is a menace to bigots, unabashedly woke, and does not suffer fools gladly. Enjoy him while you can, he won’t be around forever.

Reviews

Verified by GigSalad

Great entertainer!!

I hired Rollin for my husband’s 50th birthday party and he was fantastic! The crowd of about 60 people loved his performance and thought he was very funny. Rollin took the time in advance of the event to get to know us a bit then incorporated some of those personal pieces into his show-amazing touch to the birthday celebration!

Rollin arrived on time, he came with all of the equipment he needed, was incredibly professional, he was very funny, and really great to work with.

It is several days later and we are still receiving positive comments from our guests. I highly recommend Rollin if you are looking for a great comedian!

Rollin, thanks so much for the show-it really was a wonderful performance to celebrate a milestone birthday!!

• Rating: 5 stars

• Reviewer: Heather Turzak

• Event date: November 22nd, 2025

Very accommodating, funny and outstanding guy

We hired him for a company Christmas party and he went above and beyond for us. He opted to use his own speakers at no cost which was much larger than our original speaker, came up with a plan that he thought would be the most beneficial and let us have the final say. Rollin was very kind, funny and a pleasure to have around during the party. Would recommend him for any event.

• Rating: 5 stars

• Reviewer: Josh C

• Event date: November 30th, 2024

• Services provided: Comedian, Stand-Up Comedian

Very funny

Very funny , we wanted some good clean entertainment. Rollin provided some music with interactive jokes and funny stories involving our family and his. We'd definitely recommend for a family event. Thanks Rollin!

• Rating: 5 stars

• Reviewer: Daron Hansen

• Event date: April 28th, 2018

• Services provided: Comedian