Painting in the Streets of Tosa

Art 64 is returning for its fourth installment, and the bracket-style live painting competition is looking to fill its field of participants now.

Published On: January 30, 2025

In June, 64 artists will square off on the streets of Wauwatosa. And only one will walk away…

With a $20,000 grand prize!

Art 64 is returning for its fourth installment, and the bracket-style live painting competition is looking to fill its field of participants now.

This clash of creators consists of three rounds, with each artist choosing their own subject and then going head-to-head with another painter before a public vote determines the winner. They get 60 minutes for the first round, 75 for the second, and 90 minutes to create their masterpieces if they reach the final.

Every artist who is chosen to mix it up is guaranteed to pocket at least $100, and prize money increases the further they advance, with the final 16 painters competing for that 20,000 big ones.

The winning artwork will be hung at Wauwatosa City Hall, and the rest of the paintings will be available for sale through an online auction once the dust has settled and the big novelty check has been handed to the champion.

The application deadline is Friday, February 28, at midnight. There is no fee to apply, so there’s no harm in trying if you’re artistically inclined. And if you don’t know how to paint, you have about four weeks to figure it out. There’s gotta be some YouTube videos or a retired art teacher in the neighborhood that can get you up to speed by then.

They are taking applications now at Art64Tosa.com. Any artist over the age of 18 is eligible to compete. A jury of artists and Discover Wauwatosa staff will pick the 64 artists in the tournament, and they will be notified on Friday, March 21.

The event takes place on June 6th and 7th if you want to add it to your calendar now. In addition to the live painting competition, there will be live music, food and drinks, family-friendly activities, and local businesses to patronize. You can learn more about it at the event website. And you can learn more about painting at your nearest art museum.