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Erik von Detten as Andy "Brink" Brinker, a Southern California inline skater who secretly joins the sponsored Team X-Bladz for $200 a week when his dad's disability pay runs thin, betraying the "Soul-Skaters" who skate for fun, not money. Disney Channel premiered it on August 29, 1998, as only its third Original Movie, and it has anchored best-DCOM lists ever since.
The made-for-TV Disney Channel movies you cleared your Friday night for — Halloweentown, Zenon, Smart House, and eventually the High School Musical juggernaut. The premiere was an event, and you'd seen it ten more times by the next weekend.
The Disney Channel movie that turned every October into a ritual. Halloweentown premiered in 1998, but its real reign was the 2000s — three sequels, endless reruns, and a generation's gateway to comfort-food spookiness with Debbie Reynolds as the world's best witch grandma.
The 1999 Disney Channel movie where a kid wins a computerized house and teaches it to be his mom from old sitcoms, until PAT the house becomes a 1950s-housewife hologram and locks the family in. Entertainment Weekly has twice ranked it the best Disney Channel Original Movie ever made.
Kirsten Storms as Zenon Kar, a 13-year-old exiled from her orbiting space station to boring old Earth in the year 2049, where nobody gets her slang and she has to stop a plot to crash the station for the insurance money. Disney Channel premiered it on January 23, 1999, and "zetus lapetus" entered the vocabulary of every kid watching. It was the first Disney Channel Original Movie to get a sequel.