Jackson is often the comic relief of the series, making jokes, making people get hurt, and dancing silly. He's an indifferent student, more fond of video games, girls, and food than he is of schoolwork. He works at Rico's Surf Shop and drives a red car that he purchased for himself. His storylines often form a comedic subplot during the show.
Jackson is very much interested in sports, playing volleyball on the school team. According to Miley, he goes to basketball games once a week and likes the Los Angeles Dodgers. He also likes the Los Angeles Lakers, and enjoys watching the Tennesee Titans football games with his Dad. He likes taking challenges, and beat the world record for pogo-jumping by four hours. He also has been seen playing video games. In Bye Bye Ball he was playing on what could be the Nintendo Game Boy or Game Boy Color. Also in We Are Family: Now Get Me Some Water! Jackson is also skilled at plumbing.
Jackson is rather messy, and has made all of the Stewart family's previous housekeepers quit. However, when Lilly cleans his room, he has difficulty finding things. Despite the fact that Jackson is a teenager, Jason Earles was in his 20's when the show started.
Though Jackson has had many friends, his closest friend is Rico. His other friends include Cooper, Thor, and Oliver. Over the course of the series, he has made temporary friendships, but none of them have lasted, at least on screen.
Olivia - Cooper's sister who likes Jackson, but tells Cooper she doesn't. Episode: I Can't Make You Love Hannah if You Don't
Becky - A girl who is dubbed "Brainless Becky" (by Thor) and "Brainless, Bodacious Becky" (by Jackson). Episode: Get Down, Study-udy-udy
Julie - A girl who Jackson lies to about being a motocylist, though she does not believe him. Episode:Take This Job and Love It
Jenny - A girl who Jackson is taking to Hannah Montana concert, but is never seen. Episode: I Am Hannah, Hear Me Croak
Hannah Montana - Jackson was caught going to the same house with Hannah Montana, and began going out with her. Though Jackson loved the attention it gave him, they broke up, and were never together again. Episode: My Boyfriend's Jackson and There's Gonna Be Trouble
Natasha - A girl whom Rico hired to replace Jackson. Episode: Achy Jakey Heart, Part One
Siena - Jackson's current girlfriend. She is a bikini model, and is extremely rich. Jackson met her at the beginning of Season 4, and grew very close to her. She learned Miley's secret before it was publicly revealed, and remained with Jackson though he wasn't rich or famous. Episodes: Sweet Home Hannah Montana, Hannah Montana to the Principal's Office, California Screamin', De-Do-Do-Do, Da-Don't-Don't, Don't, Tell My Secret, Love That Lets Go, I'll Always Remember You, I Am Mamaw, Hear Me Roar!, Wherever I Go