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He moved to Malibu, California with his father Robby and sister Miley after the death of his mother. Jackson is a mediocre high school student, and has a rough time starting college in the third season. Jackson is often seen barefoot or wearing flip-flops.In an off-handed remark in "Song Sung Bad," Jackson implausibly suggests the reason for this move involved an embarrassing incident with a Tennessean girlfriend. It is also revealed in the episode "Schooly Bully" that Jackson's bare feet are ticklish.As her alter ego, Hannah Montana, she secretly lives a double life as a famous pop star. She is like any other girl, facing challenges, but endures it with the help of family and friends. Robby Ray Stewart (Billy Ray Cyrus) is the widower father of Jackson and Miley Stewart.One of the concept names for her alter ego was Alexis Texas, but the writers learned there was an adult entertainer with the same name of Alexis Texas. He is also Hannah Montana's manager, who was a former country singer.



He also imitates his father in "You Give Lunch a Bad Name" and his sister in "You Gotta Not Fight for Your Right to Party." Perhaps as a consequence of his acting skills, Jackson is also good at dodging direct questions and using weasel words.He is often asking his dad to supplement his income or to increase his allowance.In "Debt It Be" Jackson recalls selling Miley's used tissues on the internet for $37.95.This is at first because he exploits his connection with Hannah to impress his dates.

Later, in "My Boyfriend's Jackson and There's Gonna Be Trouble" a paparazzi follows Miley and Jackson home from a concert and reports that they are dating.

In "Miley Get Your Gum" Jackson saves up enough money to buy a used car and is very proud of it, until his friend Cooper tells him it's a "Girl car." Although his dad, Robby Ray, makes changes, such as changing the horn and adding a loud stereo, after Robby Ray is unable to sell it back to the original owner. He learns ping-pong well enough to beat his father.