Skyler Bolks has been voted Sioux Falls Funniest Comic three times and is a four-time winner of the Boss's Comedy Club competition. Recently crowned the champion of the Argus Leader roast of South Dakota, Skyler can provide you with a high quality show featuring quickwits, strange observations, and real life experiences.
“Neither rain, nor snow, nor sleet, nor hail shall keep the comedian from his appointed rounds."
Skyler drove 100 miles through a blizzard to make our event. Highly recommend.
Non stop laughter, we were a small group and the interaction with everyone was great. This was our first comedian for a Christmas Party very much a hit!
Worked with Skylar a few times and always great on stage. Highly recommend and looking forward to working with him again.
Skyler was very easy to work with. He provided an option for a clean show to meet the needs of our corporate holiday event. He adapted his beginning content towards the group of people he was entertaining. We enjoyed the lighthearted event!
Skyker bailed us out last minute and performed his clean act for about 50 people. Hilarious and he was really good and pulling the audience into his show. Very interactive. He’s a funny dude!
Skyler did a fabulous job, everyone at the Holiday Party really enjoyed the show! I highly recommend booking him for any event you have.
Price Range: $1000 and up
Born and raised in Sioux Falls South Dakota, Skyler is a former college athlete turned stand-up comic. He has toured all over the country performing in bars, breweries, colleges, and comedy clubs from the biggest cities to the smallest towns.
Skyler was invited to headline the North Iowa Comedy Festival in 2021, a three time Sioux Falls funniest Comic, four time Larry Brinkman comedy award winner, and has been selected to perform in multiple comedy festivals in the Midwest. His show consists of one liners and short stories about Midwestern life and the experiences from a higher perspective, literally. At six foot seven he's probably the tallest comedian you've ever seen.
When he's not performing, Skyler can be found expanding his VHS collection or dropping quarters into every pinball machine he can find.
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| December 06, 2025 • 7:00pm - 8:30pm | Christmas Party |
| April 14, 2024 • 12:00am - 1:00am | Prom/After Prom Party |
| February 14, 2024 • 7:30pm - 8:30pm | Dinner Party |
| December 08, 2023 • 8:00pm - 8:45pm | Christmas Party |
| April 15, 2023–April 16, 2023 • 11:30pm - 12:30am | Prom/After Prom Party |
| December 10, 2022 • 7:00pm - 8:00pm | Corporate Event |
| February 09, 2020 • 6:00pm - 7:00pm | Christmas Party |
| January 16, 2020 • 7:00pm - 8:30pm | Campus Event |
A well lit performance space and a PA. No podiums please.
Indianapolis, IN 
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I am a comedian born and raised in Sioux Falls, SD. I have been doing stand up for 10+ years, and have opened for the likes of Nikki Glaser and Ben Bailey from…
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