Wacky Jack's Singing Telegrams and Balloons is the #1 choice for singing telegrams, balloons, face painting, balloon twisting, and pranks in the Pittsburgh and surrounding areas. The only company of our kind to be voted "Best of the Burgh" by Pittsburgh Magazine, we pride ourselves on top notch entertainment and balloon service with a "5 STAR REPUTATION"!

No matter what you need, we make everything simple and save you money in the process. We can deliver telegrams and balloons locally or nationally, and will do our very best to make sure you are totally happy with your purchase and with our service. One thing is for sure, you've come to the right place if you want the BEST!

Nobody does it better than
Wacky Jack's !!!
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Just a few of our well known customers and recipients

Sara Hood

Wife of former Pittsburgh Steeler

Ziggy Hood

Andrew McCutchen

Pittsburgh Pirate

Tunch Ilkin

Former Pittsburgh Steeler

Marc Andre Fluery

Pittsburgh Penguin

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Yes, Dick Wolf and his family use us "exclusively" to deliver balloons to their friends and family all over the nation!


*Calls, texts, and emails

Mon-Fri  9-5

          *Delivery of Singing Telegrams and Balloons             

  Mon-Sat  9-9

    Sat 9-12

                         *Face Painting and Balloon Twisting                            

  By Appointment




Smoking: For the health and safety of our Entertainers, we will NOT enter any establishment where smoking is allowed. It is up to you, the customer, to make sure the environment is smoke-free. If we arrive and the environment is not smoke-free, the Entertainer will leave and your money will be forfeited.


Payment: Our services can be paid for in one of the following manners:

1. Zelle, Venmo, and CashApp at the time of ordering (no fee)

2. Credit Card at the time of ordering (a 5% credit card processing fee)

3. Cash at the door (you will be expected to provide a credit card to hold the payment. If for some reason, the Entertainer is not paid or there is no one there, the card will be charged) 

Refunds or Credits: While we do understand that things happen, we do NOT issue refunds or credits for any reason unless we cannot deliver your telegram, balloons, or provide the face painter/balloon twister. Once you place an order, there is an immediate amount of work, scheduling, and costs that are involved and no other customer can request your date and time.  If you cancel, the date and time you requested could have been reserved by another customer and that is money lost. We deserve to be paid, so please make sure you want our services before ordering.

Singing Telegrams

Nobody does Singing Telegrams better than Wacky Jacks! Our Award Winning services are fun, classy, and sure to put a smile on your recipient's face!


Whether you want to send a bouquet to brighten someone's day or need balloons for an event, you need to choose Wacky Jacks!

We will beat the price of any other competitor or your balloons are free!

Face Painting and
Balloon Twisting

Need a Face Painter or Balloon Artist for a children's party? Look no further!

We have talented artists on staff to make your event a huge success!


Everyone loves a good prank, and we have a long list of ideas for you. You can even give us an idea of your own and if it's not going to get us in trouble, we may consider it! Try flocking a yard with Pink Flamingos!