Video by Jessica Leibowitz

The singing telegram industry is alive and well in New York City, proof of the timeless joy of embarrassing a friend, family member or colleague. A search of companies operating locally brought us to Big Apple Singing Telegrams, a business that's been delivering personalized 'grams since the late '70s. The company has been under the auspices of Jon Shipley since 2000, where it's grown to include dozens of different costumes, songs and performers, many of whom have been in the business for several decades.

To learn more about this institution, we followed around one of Shipley's performers, Bernard Davis, as he delivered three birthday telegrams in Manhattan. Birthdays are by far the most popular reason to deliver a telegram, but Shipley says Valentine's Day is a big single-day seller for his company. They've had years of delivering 75-100 telegrams in one day—Shipley says he did nearly 40 personally one year—with the average performer delivering no more than 15 on any given day.

"You have to be sort of ready to pop out of a cake and surprise and shock someone and then the whole audience is going to follow you; you have to prepare to be the center of attention," Shipley says of the performers he hires. "I'm really looking for people who are creative and who have an edge, who can create that laughter in an audience and be bold in embarrassing people. And willing to get into these crazy costumes!"

(Jessica Leibowitz/Gothamist)

"Sometimes we write the songs, sometimes we improv the songs in the moment, as Bernard [Davis] does quite a bit." The singing telegram business is comprised of mostly last-minute bookings; Davis composes a lot of his material on the train on the way to the gigs. Songs are tailored to the character (Elvis tunes for an Elvis costume, for example), then they'll take a few facts about the person to tailor a song for them. From costume changes to delivery to goodbyes, each telegram lasts for about 15 minutes.

"New Yorkers have that edge, so you want someone with a boldness and a creative edge who can walk into a room and undo the barriers that New Yorkers have," explains Shipley. "People here have that wall up...but when this happens, the barriers come down a little bit."

"One out of 100, somebody will get enraged," Shipley admits. "I've actually been kicked out of the office."

Visit to book a personalized telegram with which to delight and humiliate your loved ones. Telegrams begin at $100 for regular costumes at $175 for celebrity impersonations. Telegrams can be delivered anywhere in the metropolitan area; travel fees apply outside Manhattan.