Singing telegrams would not be nearly as impactful without the element of surprise. My customers and I go to great lengths to ensure recipients won't be expecting a costumed musician to suddenly appear at their home, office or restaurant table. So, even when the message is sincere or sweet, there's always a bit of prankster energy involved. But some customers like to amplify the trickster aspect. Dressed as a rodeo clown, I once walked into a kitchen where a client and her neighbors were gathered and removed a vegetable from the fridge – without acknowledging a soul. “Is anyone else seeing this?” asked one perplexed witness. I attended a Deadhead wedding and wrangled a high five from a groom who'd left high five hopefuls hanging for five whole years. I've impersonated cops, a cockroach, customers, a health inspector, Rick Astley (for IRL Rick Rolls), a Jehovah's Witness and even recipients themselves.

While pranks are fair game all year round in the singing telegram world, some customers like to punk the people they love on April Fool's Day. I once strolled into a Middle Eastern eatery, clad only in a towel (a callback to an awkward encounter with the recipient's barber), and sang Bryan Adams for a befuddled restaurateur. The fake patient I channeled in 2023 takes the cake, though. Make yourself comfortable, it's story time:)

Isaac, a bald Denver dentist who treats a wide variety of patients, was the target recipient. His office had recently received a set of fake teeth in the mail from a sender who identified themselves as “M. Gilbert.” The prankster customer, Isaac's girlfriend, enlisted me to play Mike Gilbert, a patient with dentophobia (a fear of dentists), peladophobia (a fear of bald people) and photophobia (an allergy to sunlight and bright flourescent lights). Isaac's staff, who were all in on the joke, scheduled Gilbert for a midday appointment. I began brainstorming wardrobe possibilities for my unique character.

The prankster's holiday arrived. Clad head to toe in a ski mask, goggles, a coolie (the conical Asian sun hat) and mostly black, I walked into the dentist’s office and checked in for my fake appointment. I handed the receptionist a bag of costumes and wigs, in hopes that Isaac would consider disguising himself to ease two of Gilbert's biggest fears – dentophobia and peladophobia. “Is it cold outside?” asked another patient in the waiting room, confused by the weirdo in the ski mask and goggles (as if there'd been a microburst since he was outside last). A staff member called my pseudonym and escorted me into a small consultation room within earshot of the front office. Leaning into the character, I tipped my sun hat low in the front, imagining Mike wouldn't risk eye contact with Isaac – especially if Isaac wasn't wearing a wig or a costume.

The moment of truth was upon me. Isaac, wig-free and with dentist tools around his neck, stepped into the room and sat down. “What's going on?” Isaac asked. “I'm not sure how much your staff told you about me, but I have a debilitating fear of dentists. So it's really important that you not act like a dentist,” I replied, stuttering slightly. “Did you get the teeth I sent you?” referring to the fake teeth his office had recently received in the mail. When Isaac said he hadn't, I showed him the plaster teeth I'd brought as a prop.

Isaac was buying the act. I asked him if he could sing to me – to soothe my nerves – while he examined my teeth. He wouldn't, but he was willing to refer me to a dentist that could (singing dentists are a thing?). I suggested that I could sing to myself instead. Isaac excused himself, and I could hear him whispering with his staff nearby. I couldn't make out much, but I sensed he didn't want to examine such a strange patient. A staff member came in and whispered, “I have to pretend like I'm talking to you right now. He wants to send you elsewhere, but I'm gonna tell him you insist on being treated here.” The prank was going swimmingly.

Isaac had made his aversion to treating me clear. We collectively decided it was time for the big reveal. “If you see him walk by, just start singing,” suggested the staffer I'd been interacting with. When Isaac appeared in the open doorway, I stood up and began puppeteering the plaster teeth as I sang Weird Al's U2 derivative “Cavity Search” a capella.

Listening to the Muzak
hearing people scream
sitting in the waiting room
reading crappy magazines

With a toothache
this is it, pal
root canal

My molars are impacted
I’m getting gum disease
Gonna need some fillings
Got twelve cavities

Can ya help me?
Have mercy
Doctor please!

Isaac was either confused or speechless while I was singing. But upon finishing the above portion of the tune, I started laughing. Isaac finally realized what was happening and joined me. Everyone who'd been involved in the stunt, including Isaac's nearby girlfriend, was laughing at that point. “Mission accomplished” would be an understatement.

Click on the image and scroll down for smart phone captures of the grand finale :)