Upon arriving in Italy in 1500, the team hears bongo music coming from a window and goes up to investigate. They see Leonardo da Vinci playing bongo drums while tossing paint at a canvas, and Larry is disgusted to see that he is a beatnik. Otto is upset that Da Vinci's art is too abstract for Renaissance Italy and tells Da Vinci that he should be drawing the human body and painting. Da Vinci says that those traditional painting techniques are boring, and says he's "riding the vibe."
Otto decides that Da Vinci needs to be inspired to create the drawings that he is famous for, and asks Tuddrussel to flex his arm to show the stretched tendons and muscles. Da Vinci is impressed, but does an interpretive dance instead of drawing the image. Next, Otto takes Da Vinci to the Duomo of Florence, commenting on the amazing architecture inside. Da Vinci is impressed again, but instead of being inspired to draw landscape drawings, he shares a poem. Later, Da Vinci is seen making footprints with paint at his house. Otto remembers that Da Vinci also made inventions and shows him the moving gears in Larry's chest. Larry is embarrassed by this, and instead shows Da Vinci a slideshow of the actual paintings and sketches that Da Vinci is supposed to make. At first, Da Vinci is interested but then decided that they are boring and leaves for some coffee.
In a small coffee shop, the team is downhearted about how nothing has worked when Larry notices the waitress behind the counter. He comments that she seems familiar, and when Otto looks up, he realizes that she is Mona Lisa. Otto calls for Da Vinci's attention, and then holds a photo frame around Mona's head, inspiring him to paint her. Da Vinci is shown later completing the Mona Lisa. He asks Mona to smile more but realizes that her teeth are hideous. After she resumes with her famous small smile, Time Squad departs.
Tropes present in this episode include:
- Eccentric Artist: Da Vinci is a beatnik who'd rather create performance pieces and interpretive dance moves.
- I Need a Freaking Drink: Da Vinci doesn't get booze though, just coffee.
- Mona Lisa Smile:
- Scary Teeth: Mona Lisa is asked to smile a little less once everyone sees how awful her teeth are.