Tony Chiccolini is the main love interest of Jessie Prescott on the Disney Channel television series Jessie. He is also the doorman of the Rosses' building. He comes from an Italian family that has a tradition of proposing marriage in their pasta restaurant. He also likes to play bowling.
He is portrayed by Chris Galia.
Relationship With Jessie[]
Tony first meets Jessie in the series' pilot when she falls out of a cab and lands in front of the Rosses' building which how he became the Ross kids' nanny. Tony asks Jessie out in "Guided Karma" and they go on a picnic date in Central Park. Jessie is nervous about her going on her first date with Tony and tries to act like "one of the guys", with unsuccessful results. They date gets rained on forcing to end it ahead of time. When they make it back to the lobby, Tony leans over to get his jacket back from Jessie. This confuses Jessie into thinking that Tony is trying to kiss her. She panics and quickly maces him with the pepper spray Tony gave her in a gift basket earlier in the episode, ruining the moment. However, the next morning Tony tells Zuri that he actually did want to kiss Jessie because she looked beautiful with the rain in her hair.
In "Glue Whodunnit", Tony helps Jessie unglue Mrs Chesterfeild's hair and the two are forced to miss their date at the movies. At the end of episode, Tony and Jessie are on the balcony talking about their previous failed dates. Jessie thinks Tony is going to kiss her when he warns her not to move, but instead he slaps her to kill a mosquito that was on her face. In "The Tempest And Teacup", Tony and Jessie decide to go on their "third first date". Emma and Zuri then organize a reinactement of Jessie's high school prom, but Jessie is not happy about it because her old prom ended in a disaster with her getting all wet and being laughed at by her date and everyone else. Their date is interrupted when they go to rescue Bertram Luke and Ravi who are trapped in a giant teacup billboard, only to end up trapped in it themselves. Fortunately, this proves to be the perfect spot for their date and they share their first kiss. As of Season 2, Tony and Jessie are officially a couple. Their relationship expands over the entire second season until they breakup in the season finale "Break-Ups and Shape-Ups". They get back together in the season 4 episode "The Ghostess With The Mostess".
Other[]
Tony also had a fling with Victoria Montesano, a junior "doorwoman" he is training in "Break-Ups and Shape-Ups". Tony uses Victoria to make Jessie jealous, but he genuinely starts to fall for her. Victoria dumps him at the end of episode after seeing how clingy he is.
Love Rivals[]
Brody Winton[]
Jessie accepts a date with a rich guy named Brody Winton in "The Princess And The Pea Brain". Not only was Tony jealous about this, but he also found himself unable to compete against the guy because of how wealthy he is. However, Brody turns out to be a complete jerk who secretly has another girlfriend and makes fun of Tony by calling him "doorman". After his true nature is revealed to the entire family, Jessie dumps Brody and kicks hi out then accepting a date with Tony.
Officer Peaty[]
In "Green-Eyed Monster", Jessie starts hanging out with Officer Peaty and joins his improve acting at Noodle Doodle Doo. Despite Jessie not feeling anything towards Peaty nor vice versa, Tony suspects that Jessie is cheating on him and goes out on his way to make sure nothing happens. This leads to him and Emma sneaking into one of their performances in disguise. Tony unintentionally recommended in the play a scenario called "Boyfriend Stealing Cop" and then angrily blows his cover by throwing pasta in Peaty's face. His actions get Jessie fired from the improve, but Jessie doesn't care since she will still have more time to spend with Tony and forgives him. Jessie never went out with Peaty ever again after this episode.
Ted[]
While there was never any animosity between the two, Tony was massively jealous of Jessie hanging out with her ex-boyfriend Ted.
Brooks Wentworth[]
Brooks is Jessie's ex-fiance in the final episodes of season 3. He was jealous about Jessie dating Brooks because he still has feelings for her. He did, however, help Brooks out when he was broke by hiring him as an elevator operator. Tony nearly tells Jessie about his feelings while they are riding up the elevator, only to be interrupted by Brooks proposing to Jessie and leaves defeated. Tony volunteers to officiate Jessie and Brooks' wedding since he is licensed to perform wedding ceremonies after accidentally filling out the wrong form whilst trying to became a bowling official online. When Jessie breaks off her engagement with Brooks at the altar, Brooks believes it's because of Tony implying that the jealousy is mutual.