top of page
Balloon Dogs_edited.jpg


What is a Singing Telegram?

A singing telegram is a message that is delivered by an artist in a musical form. Singing telegrams are historically linked to normal telegrams, but tend to be humorous. Sometimes the artist is in costume or formal clothing. Singing telegrams are often given as a gift and virtually for any occasion or reason. At Wacky Jack's, we deliver the best singing telegrams at the best prices! Sending a singing telegram is fun for both the customer and the recipient. It is a memorable gift that is rare and unique. A singing telegram can be delivered to any home, business, school, or hospital and we ask that you get permission from the place of delivery before ordering. Our telegrams are classy, affordable, and family friendly. They are a gift that can be sent to anyone at any age and we even deliver telegrams to children.


The history of the Singing Telegram - Western Union, the American Telegraph company began offering singing telegram services in 1933. On July 28, 1933, a fan sent Hollywood singing star Rudy Vallee a birthday greeting by telegram. George P. Oslin (1899–1996), the Western Union public relations director, decided this would be a good opportunity to make telegrams, which had been associated with deaths and other tragic news, into something more popular. He asked a Western Union operator, Lucille Lipps, to sing the message over the telephone, and this became the first singing telegram. While Oslin created the singing telegram because he thought "that messages should be fun," he recalled that he "was angrily informed I was making a laughingstock of the company." As relatively few telegram recipients had telephones, most telegrams, including singing telegrams, were first delivered in person. The popularization of the telephone in the 1960s reduced telegrams in general. By 1972, Western Union was receiving a small number of requests for singing telegrams and was seeking regulatory approval on a state-by-state basis to eliminate the offering. Western Union suspended its singing telegram service in 1974, but independent singing telegram companies, specializing in often costumed personal delivery of gift messages, have kept up the tradition. Wacky Jack Entertainment is the leader in the Pittsburgh, Pennsylvania and Tri-state area for this type of entertainment.


How long does the telegram or performance last?

Performance times vary from five to fifteen minutes depending on the costume, environment, and participation of the recipient and/or audience. We generally like to keep the performance times short to make sure we preserve the "element of surprise" and "shock effect" that singing telegrams are known for, especially by Wacky Jack's. Our performers will always allow a little extra time after the performance for photos and silliness, and being experienced improvisers, they're happy to joke around with a willing audience!


Can you handle "same day" orders for the time I request?

For singing telegrams, yes we can, if the order is placed early enough in the day. However, if our schedule is very heavy or you place an order later in the day you may have to be flexible on the time. (please allow plenty of time for your local traffic conditions, weather, etc..)


Can I get a copy of the song or telegram?

We do not provide copies of our songs. If the telegram is personalized, you may request a copy from your recipient.


Do you have other costumes not listed on your site? 

No we do not.


Can your performer bring other extras like a cake, flowers, extra balloons, or such?

We can bring extra balloons but do not stop for cake, flowers, etc.


Is a Singing Telegram just for birthdays, get well, or Valentines day?

No. They are great for EVERY OCCASION & EVERY EVENT! Birthdays, Graduations, Get Well, Anniversaries, Happy Retirement, Going Away Parties, Welcome Home, Weddings, Holidays, Will You Marry Me, I'm Sorry, Congratulations, Just to say "hi", and even for no reason at all! 


Which package should I choose?

All of our packages have the same effect and the only difference is what is included in each, so it really comes down to how much you want to spend on the recipient and what you want them to have. Want them to have it all? Order the WORKS for only $79.99. On a budget and want to save? The STANDARD or SUPREME is the way to go! Either way, we are the best at what we do!


How far do you travel?

Generally, we have a 50 mile radius of each major city that we service across the United States, but will travel beyond that area for an added fee and each order is different. Please call for details. 


What are your hours for delivering telegrams?

Normally, we deliver telegrams every day except holidays, 9am -9pm. Right now due to covid, we are only delivering them M-F 9-5 and SAT 9-12.


What kinds of payment do you accept?

We accept all major credit cards, Venmo, CashApp, PayPal, and Zelle at the time of ordering. There is a 5% credit card fee for using a credit card. We also will accept cash at the door if you give us a credit card to hold it. If you fail to give us the cash, your credit card will be charged.


What kinds of lyrics do you use?

All of our songs are family friendly and in good taste. If we ask you for information to write a personalized song, you can give us complimentary, funny, or teasing content, but please keep it clean and classy. We do not use vulgar language and do not want to offend anyone.

Do you perform Strip-o-grams?

No, we do not

How many Entertainers come?

Only 1 Entertainer will arrive to perform

bottom of page