Cool World is a 1992 American live-action-animated film directed by Ralph Bakshi, and starring Kim Basinger, Gabriel Byrne, and Brad Pitt. It tells the story of a cartoonist who finds himself in the animated world he created, and is seduced by one of his characters, a comic strip vamp who wants to be real. Cool World marked Bakshi's return to feature films after nine years. The film was originally pitched as an animated horror film about an underground cartoonist, who fathers an illegitimate half-human/half-cartoon daughter, who hates herself for what she is and tries to kill him.
In 1945 Las Vegas, World War II veteran Frank Harris (Brad Pitt) returns to his mother. Riding on a motorcycle that he won in Italy during his service, Frank and his mother are struck by a drunk couple. Frank survives, but his mother dies. As an ambulance truck takes her away, Frank is transported to "Cool World", an animated city of surrealistic landscapes and random cartoon violence. He was inadvertently teleported by Dr. Vincent Whiskers (Maurice LaMarche), a doctor who created a "spike" that was supposed to take him to the real world, but brought Frank to Cool World instead. Whiskers finds Frank useful enough to run things in the Cool World while he is gone to the real world.
Forty seven years later, Jack Deebs (Gabriel Byrne), a cartoonist, is detained after murdering a man he found in bed with his wife. He creates the highly acclaimed comic book series "Cool World", which features the femme fatale Holli Would (Kim Basinger). On the night before his release, Holli summons Jack into the Cool World, and he sees Holli dance in the local dance club. After he sees her dance, Jack is teleported back to the real world. It turns out that Holli wants to enter the real world, but is forbidden to do so by Frank, who is now a police officer in the Cool World.
After he is released, Jack is transported to the Cool World once again and meets Holli and her goons, who have been encouraging his misled beliefs that he himself created the Cool World. In reality, Holli has simply been bringing him there, and Jack created his comic book series on what he's seen there, which he initially believed were his own dreams. Meanwhile, Frank is about to go on a date with his longtime girlfriend Lonette (Candi Milo), when his partner Nails (Charlie Adler), a spider, tells him about Jack's presence. Frank confronts Jack at the local Slash Club, confiscating his fountain pen, informing him that it's a dangerous weapon in the Cool World. Frank then tells Jack the truth: the Cool World has existed long before he created the comic series and forewarns him that "noids", humans from the real world, are not allowed to have sex with "doodles", the cartoon inhabitants of the Cool World. He further advises Jack not to get involved with Holli before Jack returns to the real world.
Holli brings Jack back into the Cool World, where he is taken to Holli's apartment. Holli and Jack have sex, transforming Holli into a human. While Frank attempts to mend his relationship with Lonette, he temporarily leaves detective duties to Nails. Nails receives a call from an informant named Sparks, who tells him that Jack and Holli have had sex and are leaving for the real world. Nails decides that he can do this on his own and goes off to stop Holli. Nails attempts to stop her from leaving the Cool World, but Holli uses Jack's fountain pen to suck Nails in. Jack and Holli return to the real world, where Holli sings "Let's Make Love" at a nightclub with Frank Sinatra, Jr.. Frank discovers that Nails is gone and decides to venture into the real world to pursue Jack and Holli. Meanwhile, Jack and Holli have started to flicker between human and doodle states. While contemplating their situation, Holli tells Jack about the "Spike of Power", an artifact placed on the top of a Las Vegas casino by a doodle who crossed into the real world. When Jack displays skepticism about Holli and the idea, Holli abandons him to search for the spike on her own.
Frank meets up with Jack later on, explaining that the flickering both Jack and Holli have been experiencing is the disappearance of both worlds. They decide to team up and stop Holli from removing the spike. They get Jennifer (Michele Abrams), the daughter of Jack's neighbor to drive them to the casino, and on the way, Frank explains that it was Doc Whiskers who crossed worlds and put the spike on the top of the hotel and if it were removed, it could potentially destroy both the real world and the Cool World.
Holli is escorted out of the casino for not spending any money, all the while asking about Vegas Vinnie, which is the alias of Doc Whiskers. When she spots the Doc, she tells him that she couldn't find him, but when she starts to flicker between human and doodle state again, she begins to become suspicious and starts to see through Doc's disguise and shakes him out of it, revealing his identity. Doc tries to convince Holli not to get the Spike of Power, but Holli becomes enraged and threatens Doc Whiskers with the fountain pen. When Frank, Jack, and Jennifer get to the destination, Frank pursues Holli on the casino, while Jack and Jennifer put Doc Whiskers back together after being popped by Holli's pen. Frank chases after Holli throughout the hotel, while she's still flickering from human to doodle state. While in doodle form, Holli pushes Frank off the building to his death. Holli finds and takes the Spike of Power, transforming her, Jack, and everyone in Vegas into doodles and opening a gateway between the two worlds, releasing numerous monstrous doodles. Transformed into a superhero doodle, Jack gets a hold of the spike. Holli tries to seduce it away from Jack, but instead he returns the Spike of Power to its place, trapping him, Holli and the rest of the doodles in Cool World.
Meanwhile, Nails escapes from Holli's pen and both he and Doc Whiskers return Frank's body to Cool World. Lonette discovers that Holli was a doodle when she killed Frank and explains when a noid is killed by a doodle, he is reborn in Cool World as a doodle. He is transformed into a doodle, allowing him to pursue his relationship with Lonette. Meanwhile, Jack and Holli are last seen together in the panels of a comic book. Jack (still a superhero doodle) is planning out how they will live, much to Holli's dismay.