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 was dating Jessie.


Tony is the Ross building's handsome doorman. He is of Italian descent and has a New York accent and slick, black hair. Tony is a slight airhead, but still really funny. He is very proud of his epaulets. He's also a very loyal and understanding person, as well as an all around nice guy, and is in love with Jessie. He's really close friends with the Ross family. But Emma and Morgan have been messing up his name (Emma called him Tommy and Morgan called him Timmy).

Character History

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.


Jessie Prescott - Friend/Ex-Girlfriend

Jessie and Tony-S1 E20

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.

Emma Ross - Friend

Tony and Emma are friends.

Luke Ross - Friend/Rivals

They are friends and both have crushes on Jessie.

Zuri Ross - Friend

Zuri and Tony are shown to be friends.

Ravi Ross - Friend

Ravi and Tony are shown to be friends.

Age By Season

  • 19-20 Season 1
  • 20-21 Season 2
  • 21-22 Season 3


  • 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 is hardly seen on the show.


  • New York, New Nanny (First appearance)
  • Used Karma
  • One Day Wonders
  • Star Wars
  • The Princess and the Pea Brain
  • Beauty & the Beasts (Mentioned only)
  • Tempest in a Teacup
  • A Doll's Outhouse (Mentioned only)
  • Creepy Connie's Curtain Call (Mentioned only)
  • The Whining
  • Green Eyed Monsters
  • Austin & Jessie & Ally: All Star New Year (Mentioned only)
  • Why Do Foils Fall In Love?
  • Break-Up and Shape-Up (Latest appearance)
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