Itchell "Itchy" Oliver was a career criminal with a skin condition that caused him to itch more than the average person.
Itchy had light-colored hair and pronounced lips. He wore glasses and often smoked cigars.
Itchy had been a good friend of Shaky. When Itchy learned that his dead friend's fortune had fallen into the hands of Bob Oscar "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 snuck 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. Itchy reached into his vest to grab a gun, but Tracy pulled the trigger and shot him to death through the chest and throat. 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".
- 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 Itchy did not agree to join in Shaky's newly-conceived confidence scheme.
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. In the Mr. Magoo 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 and worked with Flattop (parallel to the 1990 movie) who was voiced by Howard Morris. Because UPA didn't give the credits in a formal fashion, it's unknown who played Itchy/Stooge.
In the 1990 film "Dick Tracy", Itchy was played by Ed O'Ross.
Itchy was one of Big Boy Caprice's top lieutenants, alongside Flattop. He and Flattop killed five criminals from a rival gang at the beginning of the movie and left a message for Tracy. They later abducted Tracy and nearly killed him in Tess's basement with the boiler broken. The Kid managed to save him. Itchy, like most of the other villains in the movie, met his end in a fiery shootout with Dick Tracy and the police.
His name was given as Jake "Itchy" Rossi according to the Topps trading cards and Playmates Toys action figure.