Itchell "Itchy" Oliver was a career criminal with a skin condition that caused him to itch more than the typical person.
Itchy had light-colored hair and pronounced lips. He wore eyeglasses and often smoked cigars.
Itchy had been Shaky's best friend. When Itchy learned that his dead friend's fortune had fallen into the hands of B.O. Plenty, Itchy planned to capture Plenty and take the money. At that moment, Elia Mahoney (Shaky's widow and mother of Breathless) called on Itchy asking for help in finding a job so she could fulfill her promise of going straight. Itchy took advantage of her by telling her that Plenty was the man who stole Shaky's fortune and nearly killed her daughter. This prompted Elia to agree to help lure B.O. into Itchy's apartment.
Itchy strapped B.O. down, took off his shoes and burned his feet in order to extract where B.O. hid the money. At the same time, Dick Tracy and Pat Patton found the money in B.O.'s apartment, hidden in a carnival Kewpie doll that B.O. had won. They were about to take it back to the police station as evidence when Itchy and Mrs. Mahoney stormed in and demanded the money. Mrs. Mahoney had a change of heart, remembering her promise to go straight, and prevented Itchy from shooting Tracy by jumping in the way of a Itchy's gunshot. The bullet killed her.
Disposing of B.O. Plenty
Itchy escaped with the doll and the money, locking Tracy and Patton in the room. With the help of his accomplices, Itchy tied B.O. to to a wooden plank and sent him floating down a narrow tunnel in the sewer, where Itchy expected him to get wedged in one of the tunnel's curves. B.O. would then presumably either drown or starve to death.
Tracy and Patton tracked itchy to his hideout after he killed the other members of his gang so there wouldn't be a split of the money. Itchy fled and hid in a wedding procession, causing everyone to think that the doll with the money was a present for the bride. Junior Tracy recognized Itchy and ran to the nearest call box. Itchy shot the car's driver and hijacked the vehicle. Tess and Junior followed in another car from the wedding. Itchy hit a cow on the road and the car exploded. He managed to escape but forgot the money, which was burning up in the car.
Junior and Tess investigated the fire, and looked for a way to call Tracy. Junior confronted Itchy and was knocked unconscious. Itchy followed Tess to her car and held her at gunpoint, having her drive them away while he wore her coat and hat. Tess asked for her purse for a hanky and grabbed her lipstick while Itchy was reading a newspaper. She wrote the word "help" on the outside of the car door, signaling any police. This attracted the attention of a motorcycle cop, who Itchy shot.
Police in hot pursuit, Tess drove the car into a tunnel so narrow that the car's doors could not open, trapping herself and Itchy. She began honking the horn to alert the police. As the car was being towed out, Itchy escaped through the other end of the tunnel, and stole a squad car (not noticing at first that Tracy was also on board, riding the rear bumper).
The Starvation Death Trap
After catching a glimpse of Tracy in the reflection of a store window. Itchy sped off and backed the car up against the wall of a house, trapping Tracy inside. The owner of the house was Kitty, the widow of another one of Itchy's friends; B-B Eyes. She helped Itchy bring Tracy into the house and tied him up to an exposed pipe near a wall. Determined to get revenge, both Itchy and Kitty decided to starve Tracy by giving him only as much water as could cling to a fork and a small serving of boiled turnips.
Wasting away fast, Tracy was growing weaker as they continued their torture. Junior found a note in the abandoned squad car left by Tracy with the address of where he was taken. Junior sneaked in that night while the lights were off, untied the thinned-out Tracy's ropes and gave him his gun. When Itchy and Kitty came back in, he pointed the gun at them and had them move against the wall. Pretending to scratch, Itchy reached into his vest to grab a gun, but Tracy fired first and shot Itchy through the chest and throat. Itchy was killed and Kitty was then arrested.
Years later, both Itchy and B-B Eyes' brothers Twitchy Oliver and B.D. Eyes teamed up to get revenge on Tracy and steal a fortune that their brothers had left behind in B-B Eyes' house. Part of their plot involved creating the illusion that the house was haunted by Itchy's "ghost".
Appearances in Other Media
1960s TV Cartoon
Itchy was one of the featured villains in the 1960s humorous cartoon version of Dick Tracy produced by UPA. Itchy was sometimes paired with Pruneface. He did not interact with Tracy directly, but was instead foiled by Tracy's "funny" subordinates.
Itchy also appeared in an episode of the series The Famous Adventures of Mr. Magoo, also produced by UPA. In the episode "Dick Tracy and the Mob", Itchy looked exactly like his other show counterpart, but was given that series' Stooge Viller voice. He was one of the mobsters working under Pruneface. The voice actor is unknown.
In the 1990 film Dick Tracy, Itchy was played by Ed O'Ross.
They later abducted Tracy and attempted to kill him by leaving him tied up in Tess' basement with the boiler broken, expecting that Tracy would die in the subsequent explosion. The Kid managed to save him. Itchy, like many of the other members of Big Boy's gang in the movie, met his end in a fiery shootout with Dick Tracy and the police.
Itchy displayed some talent for disguising his voice, as he impersonated a woman from the city orphanage as part of his ruse to abduct Tracy.
Tie-In Video Games
- Nintendo Entertainment System- Itchy appears in Tracy's mug shot files where he is described as a "nervous gunman". Under interrogation, Itchy refers to an encounter with the Blank.
- Sega Genesis- Itchy appears as the boss at the end of the first level. Itchy is a henchman of Big Boy who attacks Dick Tracy with a machine gun. He frequently pauses to scratch, leaving himself open to Tracy returning fire.
Dick Tracy: Dead or Alive
Itchy was one of several villains shown as part of a large gang in issue #2 of the comic book miniseries Dick Tracy: Dead or Alive published by IDW. He was shown being taken into custody after the villains' hideout was demolished.
- Like Pear-Shape, Itchy's appearance features some elements of self-caricature by Chester Gould (according to The Complete Dick Tracy: Volume Ten, which features Itchy on the cover).
- Itchy did not appear in the live stage show Dick Tracy Starring in Diamond Double Cross, though Big Boy and his other close associates from the 1990 feature film did.
- His name was given as Jake "Itchy" Rossi according to the Topps trading cards and Playmates Toys action figure released in conjunction with the film. This contradicts the strip and does not appear in any other media.
- Itchy referred to a brother who had worked in the city sewer system. This could have been a reference to Twitchy, or possibly a second brother.
- In the 80th Anniversary flashback story, Itchy was briefly shown conspiring with Shaky though Shaky did not agree to join in Itchy's newly-conceived confidence scheme.
- In the Midnite Mirror story-line, Itchy appears as a police officer, telling B.O. Plenty's counterpart S.T. Ench that his community service was over and that he was heading out the wrong door.