Derpy Portraits: Calgary’s Most Event Entertainment
If you’re planning a wedding, corporate party, or community gathering in Calgary, you’ve probably searched for fun ways to keep guests engaged. Photo booths are great, live music is always a hit—but what about something totally unexpected? That’s where Derpy Portraits come in.
I’m Tyler Lemermeyer, an illustrator and muralist based in Calgary. Since Last December (2024), I’ve been offering live Derpy Portraits at markets, parties, and festivals. These quick drawings are essentially caricatures, intended to capture your essence and may or may not exaggerate your quirks for comedic effect.
What is a Derpy Portrait?
A Derpy Portrait is a fast caricature meant to capture your likeness—but in a way that’s just a little off. Think of the vibe when a kid draws her aunt Kelly chugging a wine bottle and titles it “Aunt Kelly’s special Gatorade.” Not perfectly drawn, but somehow spot-on in its truth and humour. That’s the sweet spot I aim for: a mix of likeness and playful exaggeration.
Each portrait is a 5x7” black-and-white drawing, sketched live in about 3–5 minutes. The results are cute, sometimes ridiculous, and occasionally a little offensive. Most importantly, every drawing is a one-of-a-kind keepsake—perfect for hanging in the bathroom, so guests can lock eyes with you during their most vulnerable moments.”
People love them because they’re quick, unique, memorable, and, above all, playful. They spark laughter, break the ice, and make any event feel more alive.
Why Hire a Live Sketch Artist for Your Event?
If you’re looking for Calgary event ideas that people will actually remember, live sketching brings something special. Watching an artist draw live is part of the fun. Guests are entertained even while waiting their turn. A silly sketch sparks instant laughter and connection, giving people something tangible to remember your event by.
Derpy Portraits work for almost any type of gathering: weddings, corporate celebrations, birthdays, community markets, bar mitzvahs, family reunions, dogs’ quinceañeras, divorce parties, or just a Thursday night—anything that could use a little derp.
How a Derpy Portrait Session Works
At an event, I set up a small booth with my markers, paper, and a tip jar. Guests can sign up for a 5-minute slot, sit for a few minutes, and leave with their own mini masterpiece. Individuals, couples, and small groups can all be drawn, though I usually recommend one portrait per card. I also provide a protective envelope so each guest can safely take their sketch home.
Packages can be tailored to your event:
Guest-Paid Portraits: I come to your event, and guests can purchase their own Derpy Portraits (starting at $20 each). Quick, silly, and guaranteed to make them think: Is my nose really that big?
Venue-Paid Experience: Your venue or event organizer covers my time, and portraits are offered free to guests, but welcome to leave tips. Anyone who participates gets a keepsake destined for the ‘random drawer of junk you never throw out, creating a fun and memorable experience for everyone.
At a recent Calgary event, Party in the Park, I drew 64 portraits in five hours—that’s one sketch every five minutes, back-to-back all afternoon. Even with a constant, lengthy line-up, I watched strangers laugh at their sketches and leave with a conversation piece. It’s a good reminder that art doesn’t always need to be serious; it just needs to be fun, even if it’s a little derpy.
Book a Derpy Portrait Session for Your Event
If you are looking for entertainment that’s different, a little weird, and guaranteed to get people talking? Derpy Portraits sessions turn a few minutes of awkward posing into laughter and a keepsake your guests will never forget.
Available for weddings, corporate celebrations, birthdays, community markets, bar mitzvahs, family reunions, dogs’ quinceañeras, divorce parties (yeah, that’s a thing), a Thursday night, or any gathering where you want something just a little different.
Click here to request a quote today and book a Derpy Portrait Session for your event
I also offer private commissions, which are perfect for Christmas gifts, retirement gifts, anniversaries, and displaying employee of the month. Order a Derpy Portrait online