Tony Chiccolini is the doorman of the building in which the Ross family live on the Disney Channel series Jessie. He is a major recurring character. He and Jessie dated from season one until they broke up near the end of the second season. They rekindled their relationship and got back together in the final season.
Background
Before becoming a doorman, he met J.J. Mayfield and gave him $2,000 to make him a famous kazoo player. Sometime in the course of the year he found out the truth and became a doorman, which is ironic because J.J Mayfield said he could "open doors". It is possible that his family was wealthy- as he paid $2,000 and his family have their own restaurant but they may have lost their money due to J.J Mayfield.
Personality
Tony is a slight airhead but still really funny. He is very proud of his epaulets. He is also a very loyal and understanding person, as well as an all-around nice guy, and he is in love with Jessie. He is really close friends with the Ross family, although Emma and Morgan keep messing up his name. Emma has called him Tommy and Morgan has called him Timmy.
Physical appearance
Tony is the Ross building's handsome doorman. He is of Italian descent and has a New York accent and slick, black hair.
Relationships
Jessie Prescott
Tony with Jessie in "Tempest in a Teacup".
Tony first meets Jessie in New York, as the new Nanny, and instantly falls for her. In The Princess and The Pea-Brain, Tony tries to ask Jessie out but doesn't have the courage to do so. However, rich boy Brody gets to her first. At the end of the episode, Jessie realises that Tony is the right guy for her and Tony asks her out, and she says yes. In Tempest in a Teacup, they share their first kiss, and Tony confirms their relationship by saying they are together. Their relationship is put in jeopardy in Break-Up and Shape Up when they both become jealous of each other's respective visitors (Jessie of Tony's friend and Tony of Jessie's ex-boyfriend), This causes them to argue in front of their guests and arrive at the decision to break-up and remain friends. They later get back together towards the end of the series.
Emma Ross
Tony and Emma are friends.
Luke Ross
They are friends and both have crushes on Jessie.
Zuri Ross
Zuri and Tony are shown to be friends.
Ravi Ross
Ravi and Tony are shown to be friends.
Victoria Montesano
Victoria "Vic" Montesano is an old friend of Tony, who was hired to be his assistant doorman in "Break-Up and Shape-Up". Jessie quickly became jealous of Vic's closeness with Tony and got revenge by reaching out to an ex-boyfriend named Ted, which made Tony jealous in return. The two bond, and Tony confides in Vic over lunch about Jessie not "understanding him," while Jessie has lunch with Ted, whom she contacted to make Tony jealous. Jessie and Tony decide to invite their visitors over for a meal, which is held at Tony's apartment. During the meal, Tony flirts with Vic, which angers Jessie, who in return flirts with Ted. Jessie and Tony discuss the situation and blame each other for their attitude, leading Tony to decide to be with Vic, who turns him down after revealing she did like him but was turned off by his jealous behavior. Tony then reveals, after Vic leaves, that he actually did have feelings for her, while Jessie admits she was attracted to Ted. Upon this realization, the couple realizes that the spark is gone and decide to break up but remain friends.
Appearances
Season One
- "New York, New Nanny"
- "The Talented Mr. Kipling"
- "Used Karma"
- "One Day Wonders"
- "Star Wars"
- "The Princess and the Pea Brain"
- "Glue Dunnit: A Sticky Situation"
- "Evil Times Two"
- "Tempest in a Teacup"
Season Two
- "The Whining"
- "Green-Eyed Monsters"
- "The Trouble with Tessie"
- "Why Do Foils Fall in Love?"
- "Break-Up and Shape-Up"
Season Three
- "The Blind Date, the Cheapskate, and the Primate"
- "Krumping and Crushing"
- "Lights, Camera, Distraction!"
- "No Money, Mo' Problems"
- "There Goes the Bride"
Season Four
Trivia
- Although his crush on Jessie Prescott started in the first episode, they didn't actually spend time together until, Used Karma.
- He first appeared in the first episode.
- He plays the kazoo, as seen in One Day Wonders.
- It is possible that he and Luke are enemies, considering that they both hit on Jessie.
- It is known that he can hot wire a car with a paper clip and a penny, since his dad taught him to.
- His grandma is in the state penitentiary.
- It is possible that he wears boxers (The Princess and the Pea Brain) but it was Zuri's story, though.
- He's allergic to wool according to Tempest in a Teacup.
- He and Jessie had their first kiss in Tempest in a Teacup.
- He's of Italian descent, and comes from a big family.He can also speak at least a little Italian (Break Up and Shape Up)
- His last name is Chiccolini, as shown on the door of his family's restaurant (The Trouble With Tessie).
- He had four first dates with Jessie Prescott.
- He knows a lot of guys, who can get hold of just about anything, which is a running gag on the show. Whenever someone asks where the strange and difficult to obtain object they got is from, they usually say "Tony knows a guy".
- He and Jessie break up in Break Up and Shape Up.
- Ever since Tony and Jessie broke up, he was hardly seen on the show.
- He and Jessie got back together in the penultimate episode of the series.
- It was revealed in "The Ghostest with the Mostest" that Tony had a passion for being a firefighter so joined the accademy, but then had to drop out because he learnt he was allergic to smoke.
- Season four is the only season where Tony appears less than five episodes; he only appears in four of them.
Gallery
