Out of Sight

1998 crime drama/romance starring George Clooney as Jack Foley, a gentleman bank robber and Jennifer Lopez as Karen Sisco, the federal agent tasked with apprehending him. Due to an impromptu hostage situation, Foley and Sisco find themselves locked in the trunk of a car together, where they quickly form a connection. Albert Brooks is Richard Ripley, a rich businessman and former fellow inmate of Foley's, with a stash of diamonds that Foley wants to steal. Don Cheadle plays Maurice "Snoopy" Miller, another former fellow inmate, a complete psychopath also looking to steal the diamonds.

Directed by Steven Soderbergh, Out of Sight is the best movie Lopez has ever made, and it helped salvage Clooney's movie career after the Batman and Robin disaster.

This Movie Contains Examples Of:

 * Action Girl: Karen Sisco.
 * Affably Evil: Subverted in that Jack isn't evil, but what else can you call a guy who actually guides a bank teller through a robbery and takes the time to assure her that she's "doing fine"?
 * Anachronic Order
 * Ascended Extra: "The Ripper" Ripley. In the book he's a very minor character, and isn't at home in Detroit when the last caper takes place. The movie expands the role - to compare Ripley's thievery to Foley's - and has him at the mansion during the home invasion.
 * Bank Robbery
 * The Cameo: Samuel L Jackson as the  Foley meets at the end.
 * Casting Gag: Probably unintentional, but Michael Keaton's appearance as Ray Nicolette puts two former Batmen in one film.
 * Continuity Nod: Michael Keaton plays the same role (Ray Nicolette) he did in Jackie Brown, another Elmore Leonard adaptation.
 * The movie had to make him a "loaner" character from the DEA (from Jackie Brown) to explain how he was with the FBI during the manhunt for escaped prisoners.
 * Daddys Girl: "My little girl... the tough babe..."
 * Dating Catwoman: Gender-reversed.
 * Death As Comedy: Snoopy's Bumbling Sidekick, White Boy Bob, has a habit of slipping and falling. Towards the end, when he has the drop on Jack, he slips and falls and shoots himself.
 * Determinator: Karen Sisco
 * Even Evil Has Standards: Subverted in that Jack isn't evil, but he still makes a point of assuring Karen that he isn't going to rape her (when they get locked in the trunk) and later knowingly jeopardizes his chance at freedom to stop his fellow robbers from assaulting a woman.
 * Erotic Dream
 * The movie plays with the audience in revealing which character is having the dream
 * The Film of the Book: An Elmore Leonard novel.
 * Gentleman Thief: Jack Foley and to a lesser extent Buddy.
 * Foley - who robs banks for easily-insured cash and without a gun - is contrasted with both Snoopy who coldly kills his robbery victims, and Evil Banker Ripley who stole more money and ruined more lives than Foley ever could (with Foley the most prolific bank robber in the FBI databases!).
 * Gory Discretion Shot: Certainly not the violent climax, but earlier in the movie a messy multiple murder is suggested with only a few oblique shots (and Glenn's twitchy, shell-shocked reaction afterwards).
 * Great Escape.
 * Held Gaze: Jack and Karen in the Miami hotel.
 * Hidden in Plain Sight: The diamonds.
 * A Match Made in Stockholm: Foley tosses Karen into the trunk of his car during his jailbreak. During the time together they talk about movies, doing time in prison... and the sparks fly.
 * Meet Cute
 * Motor City
 * My Car Hates Me: After a clever heist Foley is arrested when his car fails to start.
 * One Last Job: Lampshaded and played straight.
 * Only in Florida: Combined with Motor City. The book and movie are located in both cities - Detroit and Miami - that Leonard famously writes into most of his work.
 * Overprotective Dad: Hilariously so. Her dad (Farina) is upset that Karen is having an affair with Ray Nicolette, a married DEA/FBI agent... and yet seems more than willing to encourage her "pursuit" of bank robber Jack Foley knowing full well what Jack and Karen's "Time Outs" really mean.
 * Perpetual Tourist: Referenced. Karen mockingly asks Foley if he imagines he'll retire to some tropical paradise. He counters that he always preferred mountains.
 * Shout Out: In the car trunk, Foley and Karen argue about movie romances especially the one in Three Days of the Condor, where the kidnapped woman falls in love a little too quickly with her hostage-taker. Meanwhile, they're doing it to themselves...
 * A Simple Plan: the home invasion to nab Ripley's diamonds.
 * Sliding Scale of Gender Inequality: Karen suffers at her job - her male co-workers and superiors keep dismissing or questioning her work, the crooks she handles as a Marshal are sexist - despite her being hyper-competent, smarter than nearly every other character, and able to handle herself in a fight.
 * Spin Off: Karen Sisco had a short-loved television series called, appropriately enough, Karen Sisco.
 * The Stoner: Glenn, played by Steve Zahn, Foley's Bumbling Sidekick..
 * Suicide By Cop: Foley attempts this.
 * Sympathetic Criminal
 * Throwing the Fight: Snoopy does this in prison. He doesn't take it well when the other guy brags about his "victory".