Rollin Penner is a seasoned performer with years of experience in every kind of venue. He has performed for audiences of 20 and audiences of 1000 and everything in between. He is equally comfortable playing at a family birthday or a Saturday night Comedy Club.
Rollin will bring you anything from a 30 minute spot to a 60 minute solo show or a full 90 minute multi-performer show. He works with many talented comedians and can bring performers with him that are right for your event. His many years of experience and his friendly personality mean that he will be able to help you put together an entertainment package that satisfies your needs and your audience. His reviews speak for themselves!
4 reviews
Heather T.
November 25, 2025I 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!!
Hired as: Comedian, Stand-Up Comedian
Josh C.
December 4, 2024We 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.
Hired as: Comedian, Stand-Up Comedian
Rollin Penner Comedy
Thank you so much Josh. The whole night was a pleasure!
Shannon K.
March 27, 2023Was an amazing show and would highly recommend
Hired as: Stand-Up Comedian
Daron H.
April 29, 2018Very funny , we wanted some good clean entertainment. Rollin provided some music with interactive jokes and funny stories involving our family and his. Everything was tasteful and good, with the exception of the occasional use of the word ' Frigg, or Friggin'. We'd definitely recommend for a family event. Thanks Rollin!
Hired as: Comedian
Price range: $150-$2000
Gig length: 15 - 90 minutes
Expect a highly professional product tailored to your requirements. Clean if you want clean. Edgy if you want edgy. Never gratuitously dirty, never sexist, racist, or homophobic. Expect political and religious satire and a wide range of subject material. Expect to laugh a lot.
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 brand of 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 an experienced performer equally comfortable as a host, feature or headliner. His credits include:
-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
-over 300 comedy sketches written and performed on CBC Radio
-over 200 comic stories published in newspapers including the Winnipeg Free Press
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.
Rollin's favorite audience member reviews are:
"I thought you would be terrible but you weren't." John Andrews.
“Please don’t play that song again when I’m in the audience.”-Kathy Penner.
Friday
Christmas Party
7:30pm - 8:00pm
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Springfield, MB
Saturday
Birthday Party
10:00pm - 11:00pm
•
Winnipeg, MB
Thursday
Birthday Party
2:00pm - 2:45pm
•
Winnipeg, MB
Saturday
Christmas Party
6:00pm - 7:00pm
•
Kenora, ON
Saturday
Restaurant/Bar Event
7:00pm - 8:00pm
•
Winnipeg Beach, MB
Saturday
Birthday Party
8:00pm - 8:45pm
•
Winnipeg, MB
Friday
Birthday Party
7:00pm - 9:00pm
•
Winnipeg, MB
Saturday
Birthday Party
7:00pm - 9:30pm
•
Winnipeg, MB
Saturday
Comedy Night at the Lorette Bar
8:00pm - 10:30pm
Thursday
Winnipeg Comedy Fest
9:00pm - 11:00pm
Performer has his own PA equipment available for small or larger rooms.
Stand-Up Comedian
