Top 7 Party Entertainers in Winnipeg

Party entertainment has been around since the time of the ancient Greeks, Romans, and Etruscans, and the Middle Ages.

Back then, storytellers, jesters, jugglers, bards, and poets gave life and colour to parties, as well as highlighted the culture and wealth status of the people of those times.

Today, entertainers are still present and come in different forms to accommodate different celebration themes and needs.

Just for you, we looked into the best party entertainers in Winnipeg! Let’s look into them, shall we?

How much does it cost to hire entertainers on average?

In Canada, the average price range of hiring entertainers costs $480 up to $5,500. Solo entertainers may also cost around $800 per act and may require additional costs for extensions or subsequent hours.

Take a look at this table of some of the most popular types of entertainers and how much it will cost to hire them:

TYPE OF ENTERTAINER	AVERAGE PRICE RANGE
DJs	$470 – $950
Comedians	$760 – $1,800
Magicians	$950 – $2,000
Wedding singers	$1,400 – $2,002
Wedding bands	$1,900 – $3,800
Jazz bands	$1,700 – $2,800
Cabaret show	$2,800 – $4,700
Caricaturists	$623 – $1,091
Clowns	$260 – $330/hour
Face painters	$103 – $262/hour
Balloon artists	$221 – $303/hour

  

How we selected the best party entertainers in Winnipeg

In reviewing which companies provide the best party entertainers in Winnipeg, we selected the following entries based on these criteria:

Services offered – What types of entertainment does the company offer? Does it offer packages suitable for different party themes?

Entertainer quality – How good are the entertainers? Are they competent and punctual with their work, as well as flexible to face any changes and challenges?

Prices offered – Are their entertainment services worth paying for?

Client satisfaction – Are their clients satisfied with how the entertainers enlivened their events? Are they willing to hire the same company again?

1. Heather’s Pretty Parties

CRITERIA	RATING
SERVICES OFFERED	★★★★☆ 4/5
ENTERTAINER QUALITY	★★★★★ 5/5
> Competent and punctual	★★★★★ 5/5
> Flexible to changes and challenges	★★★★★ 5/5
PRICES OFFERED	★★★★★ 5/5
CLIENT SATISFACTION	★★★★★ 5/5

Heather’s Pretty Parties is a well-known provider of dress-up characters, storytellers, and fairy-tale-themed children’s parties.

It currently offers an impressive selection of over 125 unique characters ranging from princesses to princes, mermaids, fairies, witches, pirates, superheroes, and magical sea creatures.

Holiday dress-up characters, such as Santa Claus and Mrs. Santa Claus and their elves, are also available. 

Clients who will avail of packages with these characters will also get face painting, storytelling, song performance, photography, and a cape and crowning ceremony.

Based on our assessments, Heather’s Pretty Parties offers more characters and bundles with more fun inclusions compared to other entertainment providers.

Besides the fun characters and packages, we also appreciate Heather’s Pretty Parties for providing loot bags ($5 each) and additional crowns ($10 each) for clients who want to give more prizes to their visitors.

In terms of face painting, this entertainer provides more affordable rates. An hour of face painting costs $165 – with the painter accommodating up to ten faces in that time frame. 

We find this rate reasonable, given that other face painters in Winnipeg may cost $200 dollars an hour.

A downside though to this entertainment provider is that while it has its own venue, it can only fit up to 15 guests. 

Clients also can’t customise the venue decor as that is under the purview of the company.

That said, clients may still avail of this company’s party packages as the company welcomes hosting at different venues. They will be able to accommodate more than 15 guests and set up their preferred decorations.

Customer Reviews

Highly recommended for children’s parties

“I hired the Miracle Sister for my daughter’s 1st birthday. I can say she’s amazing! Getting all the kids engaged and her song number was loved by the adult guests. Me and my family were happy to have availed of Heather’s service. It was indeed a pretty party! Highly recommended!” – Avigail Arda 

The Cinderella I hired was perfect

“I was so impressed by every interaction I had! So professional, friendly, kind and extremely responsive. The Cinderella at my daughter’s party was perfect!! The kids had so much fun! It was truly such a special party because of it. Highly, highly recommend!” – Andrea Ormiston

2. Amazing Entertainment

CRITERIA	RATING
SERVICES OFFERED	★★★★★ 5/5
ENTERTAINER QUALITY	★★★★☆ 4/5
> Competent and punctual	★★★★★ 5/5
> Flexible to changes and challenges	★★★☆☆ 3/5
PRICES OFFERED	★★★★★ 5/5
CLIENT SATISFACTION	★★★★★ 5/5

Amazing Entertainment is a provider of various types of entertainment services for children and adults. 

We looked into its portfolio and found quite an array of games, performances, live shows, rides, and musical numbers perfect for children’s parties and adult events.

In terms of its party packages, they come with casino games, celebrity headliners, casino prizes, gift cards, and cabaret dancers.

Props and decor items are also available with the bundles. We think that these make decorating more convenient.

Clients mentioned that the upgraded value packages are worth paying for. The silver package costs $1,400 while the gold package is priced at $2,300.

We find these entertainment bundles reasonably priced, given that solo celebrity headliners can cost $1,000 and cabaret dance acts already charge $2,000 alone.

Another thing we like about Amazing Entertainment is that it offers musical acts from different genres, from folk-pop to country, electro, rock, jazz, and classical.

Clients may even get impersonators of popular singers to perform some of their well-known hits, which is great for celebrants who have favourite artists.

It is worth noting that for some of the performers, their rates aren’t displayed on the company’s website. In this case, clients may phone in or email to request quotes and the list of party bundles they can customise.

If you’re looking to throw an intimate bash, we’d advise you to look elsewhere as this entertainment company’s services are more tailored to  large gatherings – by large, we mean at least 100 guests.

Another thing we weren’t too happy to hear about is some of the staff not accommodating clients’ personal playlists. 

Apparently, for the clients who experienced this, the staff insisted on using their default setlist as they claimed it “fit” the company’s party packages better.

Customer Reviews

Effortless booking and payment

“I used Amazing Entertainment to help celebrate my husband’s retirement during the pandemic. The set up was done very early morning before he headed to work for his last day and he was so surprised when he walked out the door. Booking and payment was effortless and I will definitely return for future special occasions!” – Lori Friesen

Efficient services that make parties memorable

“A HUGE thank you, Allen and Amazing Entertainment, for ~ with just two days notice ~ installing your Sky Dancer for the surprise ‘drive-by’ for our son’s 40th! It was a hit, and it made a milestone birthday special and fun in these pandemic times.” – Geri Porath

3. LaserTopia

CRITERIA	RATING
SERVICES OFFERED	★★★★☆ 4/5
ENTERTAINER QUALITY	★★★★★ 5/5
> Competent and punctual	★★★★★ 5/5
> Flexible to changes and challenges	★★★★★ 5/5
PRICES OFFERED	★★★☆☆ 3.5/5
CLIENT SATISFACTION	★★★★☆ 4/5

If you’re looking for an action-packed way to celebrate, then LaserTopia is for you.

Its primary entertainment service is laser tag, although we learned that it also loffers arcade games, party hosts, and a fast food menu.

We visited the laser tag venue and found that kids aged 6 and up are allowed to participate in the laser tag games. 

Do note, however, that all kids under the age of 18 are required to fill out a waiver form before they get admitted into the game area.

In terms of party packages and entertainment, LaserTopia currently offers three different bundles, namely The Traveler ($219.50), Great Adventure ($249.50), and Around the World ($349.50).

A strong point of these packages is that they accommodate up to 10 guests, which we think is ideal for celebrants who want to bring friends to play laser tag.

Another favourable point of the packages is that they come with a private party room, party supplies, party hosts, unlimited popcorn and soft drinks, and set up and cleaning services.

We also have to give it to this company for offering vegan, gluten-free, and nut-free options for clients with special dietary needs.

On the downside, clients are not allowed to bring outside food or beverages to the laser tag venue. 

Having said this, we’re a bit taken aback by how limited LaserTopia’s menu is. As of writing, it currently only serves pizza, chicken wings, French fries, pop corn, and canned drinks.

It’s also unfortunate that the venue doesn’t have lockers available. We think that the company should provide these to ensure that clients can keep their belongings safe and secure while they enjoy the fun and games.

Customer Reviews

Our son had a blast with his birthday

“We had our sons 11th birthday party here this past weekend and it was an absolute blast. The party host was very helpful and the whole time was smooth and efficient. Laser tag was a hoot and the kids all enjoyed their rime with the arcade games afterward. Overall very easy to deal with the staff and very affordable considering what was provided. Thank you for easing the birthday party experience!” – dkidd14

Great place to celebrate with noise boys

“Great experience celebrating 8th birthday for a group of noisy boys. Very clean and organized, beautiful birthday rooms,friendly and helpful staff, food is delicious,we had a gluten free guest and the place provided with gluten free option without additional cost ,also tasty and looks the same,so the kid didn’t felt left out. The place is not cheap ,the same party size at the other place cost less,but the place looks fantastic and the food delicious, we are very happy with celebrating the birthday here.” – Dana NVRSK

4. Cherry Tree Productions

CRITERIA	RATING
SERVICES OFFERED	★★★★☆ 4.5/5
ENTERTAINER QUALITY	★★★★★ 5/5
> Competent and punctual	★★★★★ 5/5
> Flexible to changes and challenges	★★★★★ 5/5
PRICES OFFERED	N/A
CLIENT SATISFACTION	★★★★★ 5/5

Cherry Tree Productions takes pride in providing top-tier DJ services for more than 30 years now.  For one, Barry Kay – one of the best DJs in Winnipeg – is part of its DJ pool.

Clients mentioned that their events were superb and fun, thanks to DJ Barry Kay’s performance and ability to make parties livelier and extraordinary.

Besides DJ services, this company specialises in bar and bat mitzvahs, which is a great move as Jewish families really know how to throw a party!

We looked into the mitzvah packages and found that they come with photo booths, selfie stations, interactive games, dancers, temporary glitter tattoos, and loot bags.

Another favourable point of Cherry Tree Productions is that you can also hire them for school functions, corporate events, weddings, and even funeral wakes.

Many clients noted how their celebrations became one for the books, thanks to the talented performances and fun interactive activities the company provided.

That said, it’s just a tad disappointing that most of this company’s event packages are more suited to grown-up parties. To date, it currently doesn’t offer kid-friendly options – apart from bar and bat mitzvahs, of course.

Another limitation of Cherry Tree Productions is that its event package and talent prices aren’t displayed on its website, which is what the other entries have. On a brighter note, clients may request quotes through email or the company’s online enquiry form.

Customer Reviews

Looking forward to booking them again for the next event

“Barry Kay and Cherry Tree ran the engagement party for our daughter and her fiance last night. Barry is excellent to work with. He really knows how to keep a party moving and read the crowd to make sure that everyone is having a good time. The venue put dessert out as the dancing was starting and everyone chose to dance, rather than eat dessert! We have used Cherry Tree for many of our family events and hope to have many opportunities to work with Barry again!” – Nora Lazar

Barry was a great party planner

“It was a wonderful experience planning our event with Barry. His knowledge and expertise in music and creating a party atmosphere can’t be beat!  He created a photo journey that was thoroughly enjoyed by everyone.  The Selfie Station was excellent!  We had photos of all of our guests having a great time.  Barry knows how to get everyone up, moving and staying out on the dance floor!” – Warren Zimmerman

5. Crystal Sound

CRITERIA	RATING
SERVICES OFFERED	★★★☆☆ 3/5
ENTERTAINER QUALITY	★★★☆☆ 3.5/5
> Competent and punctual	★★★★★ 5/5
> Flexible to changes and challenges	★★☆☆☆ 2/5
PRICES OFFERED	★★★★☆ 4/5
CLIENT SATISFACTION	★★☆☆☆ 2/5

A DJ-headlined party won’t be complete without great lighting. With Crystal Sound, clients can get both licenced and expert DJs and competent lighting installers to make events livelier and more visually appealing.

In terms of entertainment services, this company currently offers customisable musical performance packages for different types of parties.

We looked into the company’s portfolio and found that it extends its services to weddings, birthdays, graduation parties, social functions, bar and bat mitzvahs, and holiday celebrations.

Apparently, Crystal Sound specialises in DJing and setting up mood lights for weddings. From what we’ve heard, newlyweds were satisfied by how the setlist kept the dance floor packed throughout the party.

On the downside, we weren’t so pleased to hear about some of the staff not following through regarding changes in the music setlist or performers.

Clients mentioned that the company changed their DJs during the day of the event without informing them beforehand, which we think is quite unprofessional.

For lights, clients mentioned that the arrangements complemented the music and decorations of the event, which we’re pleased with as set-ups contribute to the atmosphere and success of any event.

We like that Crystal Sound has an in-office showroom where you can check out different arrangement samples, which can help clients get a feel of what elements they want to use for their special occasion.

That said, it’s just a tad unfortunate that this company’s entertainment services are currently limited to DJing, musical performances, and leading dance-offs.

Customer Reviews

The sound quality was excellent and it was the right volume

“The music at a social is SO important, and Crystal Sound did not disappoint! Junior kept everyone dancing, and we were told multiple times throughout the night that the music was awesome. The sound quality was excellent and it was the right volume. We would absolutely recommend Crystal Sound. Thank you so much!” – Melissa and Ryan

DJ Josh knows how to make a dance floor packed all night

“We booked Crystal Sound for our wedding reception, and they did not disappoint!  Josh was our DJ, and the dance floor was packed all night.  I love how engaged Josh was, he looked like he was genuinely having a great time, which also kept the crowd going.  They were great to communicate with.  Thank you so much to Crystal Sound! We are SO happy we booked your services.” – Haylie Payne

6. Jentastic Entertainment Parties for Kids

SERVICES	Party Entertainers
WEBSITE	https://jentastic-entertainment-girl.business.site/
ADDRESS	Winnipeg, MB, Canada, Manitoba
CONTACT DETAILS	(431) 554-6136 [email protected]
OPERATING HOURS	Monday – Friday, 6:00 PM – 10 PM Saturday – Sunday, 24 hours

CRITERIA	RATING
SERVICES OFFERED	★★★★★ 5/5
ENTERTAINER QUALITY	★★★★☆ 4/5
> Competent and punctual	★★★★★ 5/5
> Flexible to changes and challenges	★★★★☆ 4/5
PRICES OFFERED	★★★★★ 5/5
CLIENT SATISFACTION	★★★★★ 5/5

Jenstatic Entertainment is one of the most requested entertainers in Winnipeg. Jen, the founder and owner of Jenstatic Entertainment, is a funny and charismatic individual that is not only great with kids, but is also great at capturing the hearts and attention of kids and even adults.

With her years of dedicated service, she has honed her craft and obtained skill sets that work greatly with her passion to entertain. We also like how she provided high-quality balloon animals and face painting. 

We highly recommend them for parents who want their kid’s birthday party to be a memorable one. She is very easy to deal with, and provides various discounts including the New Year discount special and discounts on the bouncy castle. 

Customer Reviews

She’s nice to talk to, very accommodating, and sweet.

“I saw Jen when I attended our churchmate’s birthday party. The kids and adults enjoyed her show. Right at that moment we knew exactly that we wanted her on our son’s birthday party. She’s nice to talk to, very accomodating , and sweet. I love how she do her magic making sure to capture the heart and attention of kids and even adults. Highly recommended” – Camille G.

She was funny, charismatic and ensured the kids were entertained by her silly tricksl

“Jentastic was at our party this weekend and we couldn’t have been happier with her services. She was funny, charismatic and ensured the kids were entertained by her silly tricks. She also provided high quality balloon animals and face painting. We were amazed that she got through all the kids on time. She is definitely the best entertainer in Winnipeg! We highly recommend!”  – Brian B.

7. Sleepy the Clown 

SERVICES	Party Entertainers
WEBSITE	http://sleepytheclown.com/
ADDRESS	Winnipeg, Manitoba, Canada
CONTACT DETAILS	(204) 791-3595 [email protected]
OPERATING HOURS	Monday – Sunday, 24 hours

CRITERIA	RATING
SERVICES OFFERED	★★★★★ 5/5
ENTERTAINER QUALITY	★★★★☆ 4/5
> Competent and punctual	★★★★★ 5/5
> Flexible to changes and challenges	★★★★☆ 4/5
PRICES OFFERED	★★★★★ 5/5
CLIENT SATISFACTION	★★★★★ 5/5

If you’re to spice up your kid’s birthday with party entertainers, then you might want to check out Sleepy the Clown. Charles Lauder and/or Sleepy the clown has been providing Winnipeg and Manitoba his clowning practices for over 20 years. 

Throughout his career, his fascination and love for people grew and so is his craft and expertise in entertaining. He will be more than happy to be in your children’s events along with his award-winning balloons and classic clown variety shows. 

He has appeared in multiple events and festivals including the Fringe Festival, Manitoba Threshermen’s Reunion, Red River Ex, Carmen Fair, teddy Bear’s Picnic, and Museum of Human Rights, to name a few. 

He is your clown whether you need high-energy stage acts, Maitoba’s greatest balloon art, or assistance in throwing the best birthday party ever. For additional information, visit their website’s balloon, show, or birthday pages, or contact and reserve your show time at any time!

Customer Reviews

BEST ARTISTS WE’VE HAD!

“BEST ARTISTS WE’VE HAD! We had Sleepy out with some of his friends for our Breakfast with Santa and we could not be happier with their work! From face paining, glitter & henna tattoos, and the AMAZING balloon art/animals the kids were beyond happy. Sleepy also did a 20min show that ALL the kids (and adults) loved. Highly recommend!” – Nicole Potter

“Sleepy the Clown came to my child’s birthday, and entertained all the kids and the adults.

“Sleepy the Clown came to my child’s birthday, and entertained all the kids and the adults.  I have seen him perform at many other festivals. To say his skills at balloon twisting is impressive would be an under statement. He is funny, engaging and tallented. I love his clown magic and juggling skills. always a please to watch.”  – Shy Pattie

FAQs on entertainers

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And that ends our impartial review of the top-party entertainers in Winnipeg!

In the meantime, we also recommend these other articles related to hosting events and setting up party themes and decorations:

• Top Event Spaces in Winnipeg
• Best Wedding Catering Services in Winnipeg
• Best Stores for Party Supplies in Winnipeg

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