Good Advice

"Barry: Damn, Cindy's got balls. Ryan: She does now."

Good Advice is a 2001 Romantic Comedy starring Charlie Sheen, Angie Harmon, and Denise Richards, written by Daniel Margosis and Robert Horn (both of Designing Women) and directed by Steve Rash (Can't Buy Me Love). The film is set and and was filmed in modern-day New York City.

Ryan Turner (Sheen) is on top of the world: he has a hot job, hot girlfriend, and can afford to treat people like gum on the bottom of his shoe. But his luck goes down the drain when he receives a bad stock tip and loses everything. He ends up moving in with girlfriend Cindy (Richards), who promptly leaves him to move to Brazil with some guy she just met.

Opportunity once again comes knocking almost instantly: Cindy left her job--and salary--as advice columnist for a small newspaper wide open. When Cindy's editor Page (Harmon) notifies Ryan of this, he immediately jumps and decides to take over the column himself ("Cindy's sick, um...Brazilian Flu"). He stumbles with the task at first, but with the help of Page's secretary Iris and his best friend Barry, he manages to make the column famous and turn himself into a decent human being.

Co-stars Jon Lovitz as Barry, Roxanna Arquette as Kathy, Estelle Harris as Iris, and Barry Newman as Donald Simpson.

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 * Alpha Bitch: Cindy.
 * Character Development: Ryan to the nth degree (see Jerkass below).
 * Page too, since she loosens up just a little.
 * Corrupt Corporate Executive
 * Dirty Old Woman
 * Hot Editor
 * Jerkass: Ryan at the start of the film. Oh so very very much.
 * Shout-Out: One scene has a Charlie Sheen movie playing in the background.
 * Soap Opera Disease: Brazilian Flu
 * Squick: The modern-art performance. Just...ew.
 * Stealth Pun: Page Henson, editor-in-chief.
 * Also qualifies for Hollywood Spelling, although it is never acknowledged in-film.