Rudy winking

Rudolph Bartholomew "Rudy" Tabootie is the main protagonist of ChalkZone. This shy daydreamer made his debut in the very first ChalkZone short featured on Oh Yeah! Cartoons (later shown on the regular series as "Rudy's First Adventure"). In the short, Reggie Bullnerd stole his lunch money, so Rudy retaliated by going up to the chalkboard and drawing his ideal superhero, Snap, fighting Bullynerd, a monster caricature of Reggie. Unfortunately, this got him in trouble with his teacher, Mr. Wilter, who punished him by making him write "Cartoons are not funny" 500 times on the chalkboard after school. As he was writing the sentences, using a piece of White Lightning brand chalk, Rudy discovered a portal to ChalkZone, where all chalk drawings went after they were erased, Rudy's among them. It was in ChalkZone that Rudy helped Snap fight off Bullynerd.

Rudy appeared again in another short featured later in Oh Yeah!'s first season, titled "Amazin' River", where he and Snap tangled with a clumsy Cyclops who guarded the Magic Chalk Mines, whom Rudy wound up drawing another eye onto.

Rudy's next appearance was at the start of the show's second season, in the short "Rudy's Date", which introduced his would-be girlfriend, Penny Sanchez. In this short, Snap reluctantly helped Rudy and Penny retrieve the pieces of her scientific formula which Reggie had erased. Starting with that short, though, Rudy's appearance changed so that he looked older. When ChalkZone became a regular series, the first two shorts were later featured as flashbacks. According to "Rudy's First Adventure", the episodes shown in the flashbacks occurred two years earlier, so Rudy apparently aged about two years between "Amazin' River" and "Rudy's Date".

In the episode "French Fry Falls", Rudy, Snap, and Penny crossed paths with the now two-eyed Cyclops from "Amazin' River", who would later be called Biclops. Thankful to Rudy for improving his vision, Biclops entitled him to letting him have all the Magic Chalk he wanted.

Rudy is quite an adventurer in ChalkZone, battling monsters, saving damsels in distress (and Penny, occasionally), drawing up a storm, and dreaming up schemes left and right. Other characters important to Rudy include ChalkZone friends like Blocky, ChalkDad, which is a caricature of his father, Joe, and Queen Rapsheeba, who is Snap's love interest. He has also made enemies with such beings as Skrawl & the Beanie Boys, the Craniacs, and Vinnie Raton.