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In 1953, Burt Ryan stepped on one of Benny Russell's drawings depicting a space station. Also, Roy Ritterhouse offered to sketch some of the Cardassians Benny described, saying they'd make a nice cover. (DS9: "Far Beyond the Stars")
In 1969, Captain John Christopher offered to sketch the layout of the US 498th Airbase Group for James T. Kirk to show him where the record section and the photo lab were. (TOS: "Tomorrow is Yesterday")
Captain Jonathan Archer kept drawings of frigate Enterprise, the aircraft carrier USS Enterprise (CVN-65), the space shuttle Enterprise (OV-101), and the NX-class Enterprise in his ready room. (ENT: "Broken Bow", "The Catwalk")
In 2151, several students from Miss Malvin's fourth grade class sent letters and drawings to the crew of Enterprise NX-01. Doctor Phlox decoded to put one up in sickbay, while T'Pol commented on their accuracy despite being crude. Trip Tucker asked her which one she wanted, the one he was holding (depicting their ship), one that appeared to show a First Contact, and a picture of a green Vulcan with oversized ears. (ENT: "Breaking the Ice")
In 2366, a kidnapped Beverly Crusher told a drawing Kyril Finn that he should be drawing, not killing people. Finn replied that he could do both. He drew several sketches of Crusher while he held her captive. (TNG: "The High Ground")
Later that year, while counselling Clara Sutter, Deanna Troi suggested that she draw her a picture of Isabella so that she could see what the girl's imaginary friend looked like. (TNG: "Imaginary Friend")
While trapped in the Ancient West holoprogram and attempting to figure out a strategy to beat a Data-faced Frank Hollander in a gunfight, Worf drew a map showing his, Deanna Troi and Alexander's positions. Eli Hollander expressed his desire to find the artist who had drawn his likeness on a wanted poster, saying if he did, "he'll be sorry he ever put pen to paper" adding that he (Eli) was "ten times uglier than that, ain't I?". (TNG: "A Fistful of Datas")
In 2370 when Nikolai Rozhenko announced his intention to replace Vorin as the Chronicle for the Boraalans, Worf told him that he was never good at drawing, but Rozhenko said he learned quickly. Keeping the BOraalan chronicle was an important part for the Boraalans. (TNG: "Homeward")
Also that year, a Takrit was rumored to have been apprehended by the Kazon-Pommar while making a sketch of the site of a conference for all First majes. According to Neelix, the Takrit were not known for their art. (VOY: "Alliances")
Molly O'Brien loved to color. (DS9: "Accession", "Doctor Bashir, I Presume", "Time's Orphan") In 2373, Miles O'Brien promised to color with her so she wouldn't feel left out now that Kirayoshi O'Brien had been born. (DS9: "Doctor Bashir, I Presume")
Also that year, Miles O'Brien showed Dr. Bashir a picture drawn by an older, feral Molly O'Brien following her return from a time portal. Bashir noted that she anthropomorphized the landscape (drew faces on inanimate objects). Later, after returning, an 8 year old Molly showed a similar drawing to her parents, who expressed their approval. (DS9: "Time's Orphan")
In 2375, Neelix gave an ill Seven of Nine a drawing that Naomi Wildman did for her, though he couldn't tell whether it was supposed to be the USS Voyager or an asteroid belt. (VOY: "Infinite Regress")