Tony Chiccolini is a recurring character in JESSIE. He was the doorman of the Ross Penthouse. He’s a major recurring character. He was dating Jessie until the episode Break-Up and Shape-Up. They got back together in The Ghostest With the Mostest. He is a love interest for Jessie.

Tony is portrayed by Chris Galya.


Tony is the Ross building's handsome doorman. He’s Italian-American, has a New York accent and slick black hair. Tony is a slight airhead, but still really funny. He’s very proud of his epaulettes and mentions them a lot. He's also a very loyal and understanding person, as well as an all-around nice guy. He’s also somewhat childish.

He's really close friends with the Ross family. However, Emma and Morgan have been messing up his name (Emma called him Tommy and Morgan called him Timmy). Emma called him Tommy in the episode "Green-Eyed Monsters."  

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Character History

Tony in his uniform

Before becoming a doorman, he met con-artist J.J. Mayfield and gave him $1200 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." 


  • Although his crush on Jessie Prescott started in the first episode, they didn't actually spend time together until Used Karma.
  • Season 1 has the most of Tony's appearances as a recurring character.
  • In the episode One Day Wonders it’s revealed that Tony plays the kazoo.
  • It’s possible that he and Luke are rivals, considering that they both hit on Jessie.
  • He’s very childish.
  • His dad taught him how to hotwire a car with a paper clip and a penny.
  • His grandma is in the state penitentiary, this grandma is probably not Elda.
  • He's allergic to wool according to Tempest in a Teacup. Jessie gave him a wool scarf and said that he's a little bit allergic to wool, instead he is. He ends up fainting.
  • In Tempest in a Teacup it’s revealed that Tony is ticklish.
  • He and Jessie had their first kiss in Tempest in a Teacup (when they were stuck in a large teacup on a billboard).
  • 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 Jessie and the Ross family asks where the strange and difficult to obtain object they got is from, they usually say "Tony knows a guy".
  • He and Jessie broke up in Break-Up and Shape-Up .
  • Tony's family has a history of proposing in their family restaurant.
  • He thinks open doors is an "art".
  • He likes Power Ponies, thus it's revealed that he‘s a brony. (Krumping and Crushing)
  • His first appearance in Season 4, was in A Close Shave.
  • It was revealed in No Money, Mo’ Problems that Tony still had feelings for Jessie and wanted to get back together with her.
  • He’s the mayor of a small town of Illinois.
  • He‘s licensed to officiate weddings.
  • He and Jessie got back together in The Ghostest With the Mostest.
  • He wanted to be a fireman.
  • He’s a movie or TV studio security guard in Jessie Goes to Hollywood.


Season 1

Season 2

Season 3

Season 4


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To view the Tony Chicolini gallery, click here.

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