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Stakeout is a 1987 comedy/action film directed by John Badham.

The story starts with Richard "Stick" Montgomery (Aidan Quinn), a convicted murderer who, along with his cousin Caylor Reese, escapes from prison. With no hard leads the FBI elects to stake out Stick's known associates. After the FBI reaches out to the local cops for manpower support, Seattle detectives Chris Lecce (Richard Dreyfuss) and Bill Reimers (Emilio Estevez) are assigned to the night shift staking out Stick's old girlfriend Maria McGuire (Madeleine Stowe).

Chris and Bill set up a stakeout in the house across the street from Maria's. They soon discover that Maria is an extremely good-looking young woman. While Chris is impersonating a telephone repairman to put a bug in her phone, they hit it off. Soon romance blooms between Chris and Maria, which forces Chris to conceal his real identity from Maria and his new relationship from the rest of the Seattle PD. Meanwhile, Stick is still out there, leaving a trail of chaos.

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Star-Making Role for Madeleine Stowe. Forest Whitaker appears as Jack, one of the cops on the day shift stakeout team.


Tropes:

  • Actor Allusion: To pass the time while on stakeout, Chris and Bill are playing a guessing game where they cite memorable lines of dialogue and quiz the other as to what movie it's from. Bill, in an over-the-top way, recounts the line: "This was not a boating accident!" Chris, after a moment's pause, replies "I don't know." The line is from the film Jaws, spoken by Matt Hooper — a character played by Richard Dreyfuss.
  • "Be Quiet!" Nudge: Chris is unpleasantly surprised when he enters Maria's house to find the very much not-dead Stick there. He just barely avoids getting murdered by pretending to be an ex-con boyfriend of Maria's. To avoid Bill giving the both of them away when Chris meets him in front of the house, Chris knocks him out with a punch to the face.
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  • The Cavalry: And an aversion of Neutral Female. The long fight sequence between Chris and Stick in the sawmill ends with Stick getting the gun and Chris seemingly being done for. That is, until Maria, not seen since Stick ditched her down by the dock, pops up out of nowhere and whacks Stick in the head with a hunk of wood.
  • Eyepiece Prank: Part of the practical joke rivalry between Chris, Bill, and the two day shift stakeout cops involves the day shift cops doing the old ink-on-the-eyepiece prank. Bill falls victim.
  • Celebrity Paradox: The trivia game Chris and Bill play reveals that Jaws exists in this universe, which raises the question of why Chris looks so much like the guy who played Matt Hooper.
  • Chekhov's Gunman: The hoodlum that Chris and Bill get embarrassed by when, in their first scene, they chase him but fail to catch him down by the docks. At the end of the film he pops back up as the guy driving the boat that is Stick's getaway vehicle.
  • Meet Cute: Chris winds up falling in love with the woman he's staking out.
  • The Peeping Tom: They aren't really Peeping Toms, they're doing their job! But it still comes off like this sometimes, like when Chris and Bill first see Maria coming home, watch through a telescope as she gets undressed for the shower, and then mourn in despair when she shuts the bathroom door.
  • Plot Hole: Chris starts coughing and frantically trying to disguise his voice when Maria calls him and he realizes the day shift cops will be listening. But that doesn't explain how the cops, who are actively tapping Maria's phone, can't find out what number she called.
  • Reports of My Death Were Greatly Exaggerated: Stick actually says "reports of my demise were greatly exaggerated" when talking to his getaway contact. (He was presumed dead after driving a car off a bridge but actually managed to escape and swim away).
  • The Stakeout: Chris falls in love with the woman he's staking out. This leads to problems, like when he wakes up in Maria's bed after sex and realizes that the day shift cops have already arrived and are watching from the observation post.
  • Villain Opening Scene: The first scene is Stick and his cousin breaking out of prison. Chris and Bill aren't introduced until the next scene, and the story really gets rolling in the scene after that where they're assigned to stake out Maria's apartment.
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