How much does a Live Wedding Painting cost

Questions to Ask Before Hiring A Live Wedding Painter, Part 1

October 22, 2024

A Guide to knowing which questions to ask prospective Live Wedding Painters

POV: You were scrolling your TikTok or Instagram feed one night landed on a Live Wedding Painter —a stunning painting capturing the magic of a couple’s first dance or a sweet moment from the ceremony, LIVE, on their wedding day! And newly engaged, you’re thinking, I so need that for my wedding! You’ve saved the video, maybe followed a few artists, and now you’re ready to make it happen! But where do you start … and what questions do you ask about this new wedding trend that’s gone viral! We’ve compiled a list of great questions to ask before hiring a Live Wedding Painter to be sure they are the best fit for your wedding day.

It’s so important to ask the right questions to better understand an artist’s style, personality, and experience also in line with your vision and expectations. We’ve taken the last decade of phone calls with potential couples and created an easy list to help you vet potential Live Wedding Painters … book mark, save, share this post to have on hand during your next discovery zoom or phone call!

Tips to hiring a live wedding painter
Live Wedding Painting in Charlottesville, VA – Image by Sidney Leigh Photography

1. How many weddings have you painted?

Let’s start with the basics: experience! It’s one thing to be a talented artist in a studio setting with completely controlled lighting, temperature, and elements. And it’s another to take that studio into a wedding day that can be fast-paced, emotional, full of unexpected moments, with ever changing elements around you. You want to be sure the Live Wedding Painter you’re considering is someone who’s been through the wedding day chaos before and knows how to roll with it. The more weddings they’ve painted, the better.

With a decade of experience, Live Wedding Painter, Ben Keys has painted for over 400+ weddings and events. In that time, he’s learned (and still learning!) that the wedding day is the classroom. It’s the tiny technical details like realizing that the paint drys significantly slower in higher and dryer altitudes like Colorado! And on the flip side, it can be so humid in the South that the paint feels impossible to dry! Or how about traveling with a paint palette and/or a large canvas through TSA and baggage! Just this last weekend, Ben realized that his easel can’t be set up in gravel! That was a new one! Just like with a wedding photographer, there is so much about being a Live Wedding Painter that can only be learned with experience.

Live Painting at Atlanta History Center Wedding with Swan House
Live Painting at Atlanta History Center, The Swan House by Live Painter, Ben Keys

2. Describe your painting style.

Every artist has a signature style. When it comes to hiring a Live Wedding Painter, style is everything. The entertainment experience is incredible, but at the end of the day, let’s be honest: Would you hang this painting in your home? This painting will take up prime real estate on the walls of your home. This isn’t like your wedding video or wedding photo album that can be tucked away on a coffee table or styled in small frames. We’re talking above the mantel kind of big, bold, and always there to greet you when you walk into the room. The Live Wedding Painter’s style has to feel like you and fit with not only your wedding vibe … but your interior design vibe, too!

Do you prefer an abstract, dreamy, impressionist style or a more realistic painting that captures the likeness of not only the couple, but guests and the background, too. Do you like how the couple’s faces are painted? What about how the guests are painted?

Pro Tip: Make sure the painter has examples of paintings from venues similar to yours. For example, if you’re tying the knot with a dreamy Charleston low country marsh view, but the paintings you’ve seen are all from indoor ballroom weddings, double-check that artist can also capture the beauty of outdoor marsh scenes, too. You want a Live Wedding Painter that can bring your specific venue to life beautifully on canvas.

Vizcaya Museum Wedding, Live Wedding Painter
Vizcaya Museum Wedding, Live Wedding Painter, Ben Keys

3. What’s their Artistic Background?

What’s their story? Why Live Wedding Paintings and how did they get here? How long have they been painting, and not just weddings? Have they ever been represented by an art gallery, museum, or held an art show? Were they a portrait artist? Any formal art school training?

When we talk with prospective couples here at Ben Keys Fine Art Studio, we share all the time: Ben started out as a coastal landscape painter, creating paintings for both galleries and private collectors. He studied painting at the prestigious School of the Art Institute in Chicago. And it runs in the family: Ben’s mother and sister are also full time artists represented by galleries along the East Coast!

Questions to ask before you hire a Live Wedding Painter
Image by Sarah Greig Photography

4. Have you traveled with your painting gear before?

If you’re wedding is out of town, and especially if you’re planning a destination wedding, this question is key! There’s an art to traveling with a large canvas, easel, and paint supplies. It can be tricky! You want to hire a Live Wedding Painter that’s familiar with packing everything safely to avoid last-minute stress or worse case scenario, damage to the painting.

Here in the studio, we have a joke that Ben can go actually go through TSA faster with a paint palette box than Jen can her makeup bag! Ben took his first flight for a live wedding painting the first year he began painting and has become a pro over the years in how to not only pack his gear safely, but minimize additional baggage fees along the way! Fun Fact: large canvas stretcher bars can’t fly! You want to hire an artist like Ben, who’s mastered traveling with all the necessary supplies to make sure your painting is not only perfect but protected!


5. Is the Live Wedding Painter insured?

This isn’t the most fun question to ask, but it’s another improtant of the questions to ask before hiring a Live Wedding Painter. The reality is that accidents happen. We’ve seen them happen over the years! Like that time an entire table collapsed just feet from the easel, sending a huge floral centerpiece crashing inches away from Ben and his setup. (Thankfully Ben and the guests were okay!) Many venues will require that all vendors have insurance. It’s crucial that your artist is able to provide proof of insurance if the venue or planner requests it. The truth is, it’s not hard to obtain liability coverage, not that expensive, and provides so much peace of mind to you and the venue!

Questions to ask a Live Wedding Painter before you hire them
Image by Sarah Greig Photography

Stay tuned for Part 2!

Booking a live wedding painter is such an elevating experience for guests the night of your celebration, and most importantly, becomes a lasting heirloom! By asking these essential questions, you’ll find an artist who’s style you connect with, and also one who is seasoned, prepared, and ready to capture the magic of your wedding day.

But hold on, we’re just getting started! In Part 2, we’ll dive deeper into more questions to ask as you’re considering a live wedding painter for your big day. Don’t miss it!

If you have questions for Ben, we would love to schedule a call to talk more! Reach out to us here!