Rollin Penner Comedy

Top Performer

Winnipeg, MB

$150 – $2,000 per event

Travels up to 120 miles

Get a free quick quote
Promotional video thumbnail 1 for Rollin Penner Comedy

Married with Children

Promotional video thumbnail 2 for Rollin Penner Comedy

Religious sex ed

Promotional video thumbnail 3 for Rollin Penner Comedy

Aging gracelessly

Gallery photo 1 of Rollin Penner Comedy
Gallery photo 2 of Rollin Penner Comedy
Gallery photo 3 of Rollin Penner Comedy

Overview

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!


Reviews

4 reviews

Small thumbnail image for reviewer Heather T.

Heather T.

November 25, 2025
Verified review

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!!

Hired as: Comedian, Stand-Up Comedian


Small thumbnail image for reviewer Josh C.

Josh C.

December 4, 2024
Verified review

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.

Hired as: Comedian, Stand-Up Comedian

Small thumbnail image for Rollin Penner Comedy

Rollin Penner Comedy

Thank you so much Josh. The whole night was a pleasure!


Small thumbnail image for reviewer Shannon K.

Shannon K.

March 27, 2023
Verified review

Great

Was an amazing show and would highly recommend

Hired as: Stand-Up Comedian


Small thumbnail image for reviewer Daron H.

Daron H.

April 29, 2018
Verified review

Wife's 60th birthday dinner

Very 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

Write a review

Booking information

Price range: $150 – $2,000 per event

Gig length: 15 - 90 minutes

What to expect

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.

About

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.

Upcoming booked events

December 2026

04

Friday

Corporate Event

8:30pm - 9:30pm

•

Winnipeg, MB

Past booked events

November 2025

28

Friday

Christmas Party

7:30pm - 8:00pm

•

Springfield, MB

22

Saturday

Birthday Party

10:00pm - 11:00pm

•

Winnipeg, MB

March 2025

27

Thursday

Birthday Party

2:00pm - 2:45pm

•

Winnipeg, MB

November 2024

30

Saturday

Christmas Party

6:00pm - 7:00pm

•

Kenora, ON

March 2023

18

Saturday

Restaurant/Bar Event

7:00pm - 8:00pm

•

Winnipeg Beach, MB

October 2022

15

Saturday

Birthday Party

8:00pm - 8:45pm

•

Winnipeg, MB

December 2018

14

Friday

Birthday Party

7:00pm - 9:00pm

•

Winnipeg, MB

April 2018

28

Saturday

Birthday Party

7:00pm - 9:30pm

•

Winnipeg, MB

21

Saturday

Comedy Night at the Lorette Bar

8:00pm - 10:30pm

12

Thursday

Winnipeg Comedy Fest

9:00pm - 11:00pm

Setup requirements

Performer has his own PA equipment available for small or larger rooms.

Check out these featured profiles

Featured

Jody Fuller: Comedian. Speaker. Writer. Soldier.

4.97 (126)
Top Performer
131 Verified bookings

  • Birmingham, AL
  • Corporate Comedian
  • Contact for pricing

Wilma S. said “Jody was great! We had him come to a women’s fundraiser at our church. Easy to work with and such a great personality. We would definitely invite him back. ”
Featured

Frank Andreen

5.0 (1)
2 Verified bookings

  • Hawley, MN
  • Stand-Up Comedian
  • Contact for pricing

Matthew A. said “Every year, our church does a Harvest Festival and we bring in an entertainer or performer. Last year, we had Frank. He brought passion, humor and music in his unique and lighthearted way! We love... ”
Featured

Ben Marcotte

1 Verified booking

  • Minneapolis, MN
  • Stand-Up Comedian
  • Contact for pricing

Ben Marcotte is originally from rural Minnesota but is now based in Minneapolis. His unique blend of storytelling covers various topics from being a...
Featured

Lola Lemon Drag Queen Host and Comedian

5.0 (8)
Top Performer
10 Verified bookings

  • Minneapolis, MN
  • Drag Queen
  • Starts at $100

Haley F. said “Lola was amazing. From the planning of the event to the day of, Lola Lemon was INCREDIBLE! Such a fun add to a bachelorette party! She made everyone feel included and we all had the best time! ”