Artsy Smartsy is an episode of the ALVINNN!!! and The Chipmunks series.
Theodore helps Simon get past his perfectionism in order to complete an assignment for art class.
The Chipmunks and The Chipettes are in Miss Kate's art class, and while The Chipettes and Theodore have great art pieces to show off, Alvin takes an extreme approach to minimalism and Simon can't paint a bowl of fruit even if his life depended on it. Jeanette informs Miss Kate about Simon's perfectionism of everything before their teacher reveals their next assignment - a piece of new art from any medium that tells something about the artist. Simon expresses his displeasure with art, as he itches his hives. Eleanor attempts to provide a useful reason for learning art but Simon counters her argument with a simple photo from his phone. Theodore offers to teach Simon some tricks though Simon decides to try to complete the assignment himself. He takes a stab at painting, drawing, clay sculpting, and paper mache, all ending badly. Needing help, he reluctantly asks Theodore. They meet outside where Theodore wants Simon to use his imagination looking at clouds. Thinking too literally Theodore has Simon draw without looking at the paper; when he returns, Theodore finds Simon on the floor as the result of looking at the paper and erasing a hole into it. Theodore has him try again as he meets Cheesy to complete Alvin's art assignment, where they run into a canvas covered in paint. He checks on Simon again and is disappointed to find that Simon invented a robot to create art for him. To keep Simon on track, Theodore stays with him, hitting him in the forehead with jelly beans as motivation until Simon has an idea. On due day for the assignment, Simon's art receives the most attention as Alvin pleads for attention on his "Candy Horror" piece.
- "Does Not Compute" 
- The song in this episode was written by AwkwardMarina.