Flip, a recurring character from Winsor McCay's *Little Nemo in Slumberland*, debuted as an antagonist before evolving into a companion. He possesses a green face, exaggerated features, and a balding head, consistently depicted wearing a top hat and vest while smoking a cigar. Despite his middle-aged appearance, others often call him a "little boy" or "kid," though he claimed to be 23. His round shape is an illusion created by clothing; alternative outfits reveal a slim physique similar to Nemo's. His green skin is treated as natural within the narrative, described as "made for carnivals." Initially disruptive, Flip interfered with Nemo's quest to reach Princess Camille in Slumberland. His top hat, emblazoned with "Wake Up," ended Nemo's dreams upon sight. Motivated by amusement and a desire for the princess, he served as the strip's primary antagonist. His ability to disrupt dreams linked to his familial ties with the Dawn Guard, controllers of the sunrise, granting him some immunity from Slumberland's punishments. His role shifted when Nemo saved him from execution by King Morpheus' firing squad, transforming their relationship from adversaries to companions. They were later joined by a mute African Imp. Persistent rudeness eventually led Nemo to challenge Flip to a fist fight. After losing, Flip agreed to behave and follow Nemo's lead, temporarily quitting smoking. Though he resumed smoking after an abduction by monkeys, he generally maintained better conduct unless provoked, solidifying a genuine friendship. Flip exhibits a complex personality: mischievous, fun-loving, self-centered, yet resourceful, quick-witted, and occasionally loyal and brave. He enjoys troublemaking, fooling adversaries, and flirting with Princess Camille. He prioritizes self-preservation, evidenced by blaming Nemo entirely for unleashing the Nightmare King despite shared responsibility. Personal habits include a recurring struggle to quit cigars, reportedly swearing them off annually, and specific preferences like Boston brown bread, of which he once bought 5000 loaves. His background includes a grandfather who fought at Gettysburg and an ability to speak Mandarin learned in China. Animated adaptations retain his core traits. The 1911 short *Little Nemo* shows him gesturing and smoking with Impie. The 1921 *Flip's Circus* focused on him. In the 1989 film *Little Nemo: Adventures in Slumberland*, his troublemaker reputation leads him to lure Nemo away from duties. After convincing Nemo to unlock the forbidden door releasing the Nightmare King, Flip betrays Nemo by shifting all blame onto him. Facing execution via cannon firing, Flip is spared when Nemo intervenes, leveraging Flip's possession of a coded map to Nightmare Land. Flip's negligence later sinks their ship, ruining the map with water. Kidnapped by the Nightmare King's minions and rescued, he is last seen flying over Slumberland on a giant crow, coughing from an oversized cigar. Cultural analysis notes Flip's visual design and treatment reflect early 20th-century Irish stereotypes, incorporating elements like pale skin (visible in boxers), clownish/minstrel attire, and a narrative racial hierarchy where he is mistreated by characters like the Princess but ranks above the African Imp, aligning with historical conflations of Irish and Black people as inferior races.