This film provides examples of:
- Alliterative Name: Darnell Davis (Slide). After being fired from The Tower, Enrique gets a job at a place called "Shake Shack".
- Ambiguous Situation: Is Slide's surname really "Davis" or is it a fake name created to trick Mr. Simon?
- Ambiguous Syntax: Josh's apology to Shaw is worded rather ominously, with him hoping to make things right and pay him back for what he done.
- Armor-Piercing Question: "If you care about Lester, then how come you haven't asked whether he's alive or dead?" Although this doesn't wound Shaw, so much as cause him to drop the act and present his Smug Snake card and pass it forward.
- Artistic License – Law: Josh and friends barter a lenient sentence is exchange for the ledger containing evidence of Shaw's fraudulent dealings. In Real Life, since the proof was stolen from Shaw, it would not be admissible in a court of law under the Fourth Amendment.
- Actor Allusion:
- Josh telling Slide about a Chevy Nova, a car that Eddie Murphy has driven before.
- Casey Affleck has experience in pulling capers.
- Once again, Matthew Broderick has trouble with a red Ferrari.
- Badass Boast: "Sharks are born swimming." This is said by Josh's acting attorney, who just effectively blackmailed the FBI into letting Josh's group off the hook three days after passing her bar exam.
- Bad Boss: Zigzagged and downplayed with Mr. Simon. He does fire Josh for smashing up Shaw's Ferrari, which is somewhat understandable since Josh's revenge was illegal, but he also goes about firing Charlie and Enrique just for being there. On the other hand, he does give Charlie his job back when he asks for it and ensures Lester will be back at work once he gets out of the hospital, proving he's not totally unreasonable.
- Benevolent Boss: Josh Kovaks truly cares about the workers in the Tower. Ultimately, it is this level of empathy that drives him to plot the heist
- Beware the Nice Ones: Josh is a gracious employer who cares about his subordinates, as well as a charismatic individual who gets along with the residents. However, when he discovers that Shaw swindled his employees out of money, he takes a golf club to Shaw's Ferrari. Subsequently, he plots a heist to reimburse his employees.
- Bitch in Sheep's Clothing: Shaw does a very good job of coming across as a Cool Old Guy who's Nice to the Waiter for the first part of the film before being exposed as a ruthless Jerkass and con man.
- Bittersweet Ending: Shaw is sent to prison for life after his scams are fully revealed, yet Josh is sent to jail as well for the robbery. However, the FBI manages to reduce his term to two years and let Slide, Lester, Odessa, Enrique, Fitz and Charlie go free in exchange. They manage to recover Shaw's Ferrari (which they hid in his pool), and divide the solid-gold car parts among the older members of the Tower's staff.
- Black Dude Dies First: Slide is afraid the trope will be invoked.
- Blackmail: When Josh returns to the Tower to collect data for his plan, he blackmails Manuel into letting him in by threatening to tell Mr. Simon about something involving Manuel and a woman who lives in apartment 2813.
- Miss Iovenko tops that by leveraging Arthur Shaw's ledger with all his illicit dealings in exchange for her clients' freedom.
- Broken Pedestal: Josh's respect for Shaw quickly collapses when he learns he took Lester's money knowing that he wouldn't invest it.
- But for Me, It Was Tuesday: When Josh and Claire get drunk together, she says she ended up with a fireman. When Josh asks when it happened, she said it was Tuesday.
- Butt-Monkey: Everyone of the workers of the Tower to a degree, but the award goes to Mr. Fitzhugh. For having the most potential to succeed in life out of the entire group he tends to get the short end of everything until the end.
- The Cameo:
- Kate Upton as Mr. Hightower's Mistress.
- Heavy D as Courthouse Guard
- Željko Ivanek as FBI Director Mazin
- The Caper
- Casual Danger Dialogue: While lowering Shaw's car out of the penthouse window...Josh: You know what? I don't want you speaking to me for the rest of the robbery!
- Celebrity Paradox: At one point in the Macy’s Thanksgiving Day Parade, a character balloon of Shrek can be seen. Slide is played by Eddie Murphy, who voices Donkey in the Shrek films.
- Chekhov's Gun:
- Arthur Shaw's Ferrari.
- The pool cover.
- Lester's attempted suicide.
- Mr. Fitzhugh's apartment renovation.
- Shaw's monologue about using unexpected sacrifices to win in chess.
- Chekhov's Gunman: Miss Iovenko, the Tower employee studying for her bar exam, who uses her abilities to act as Josh's attorney.
- Chess Motifs: The Marshall Swindle.
- Citizenship Marriage: Odessa is desperately wanting a husband so she won't be deported back to Jamaica.
- Comically Missing the Point: Exaggerated with the conversation about lesbians during Josh's heist plan.
- Cool Old Guy: Lester, the aging doorman, is a charming individual who gets along with the employees and residents. Lester gets a shining moment when he steals a truck to divert attention from the heist.
- Crash-Into Hello: Josh and Claire meet when she clotheslines him to the ground because he's interfering with an FBI sting against Shaw.
- David Versus Goliath: Invoked when Miss Iovenko states her intention to essentially blackmail the FBI- and by extension the United States Government- in order to get a favourable outcome for the rest of the Tower employees on her third day as an officially-qualified lawyer.
- Deadpan Snarker: Charlie.
- Deconstructive Parody: Of heist movies. Only one member of the crew is a criminal, and a petty one at that. The big heist gets messed up before it even starts.Mr. Fitzhugh: You brought a stolen car to a robbery?
- Disproportionate Retribution: A chain of retribution, so to speak. Lester tries to commit suicide, Josh destroys Shaw's Ferrari. This in turn causes Shaw to demand that Josh apologize and secretly has plans to sue him, which in turn causes Josh to plan the titular heist.
- Distracted by the Sexy: At a crucial moment, Manuel distracts the security team by showing them a copy of French Playboy featuring one of the tenants.
- Do Not Call Me "Paul": Slide's exact words are: "Call me Darnell one more time, I will beat you to death."
- Driven to Suicide: Lester tries to kill himself by walking in front of a moving subway train, but is pulled out of the way at the last second, leaving him injured but alive. Upon getting caught driving a stolen truck to distract the agents, he falsely claims it's another suicide attempt.
- Establishing Character Moment: Shaw is displayed to be a nice guy, right until Mr. Fitzhugh tells Josh, Charlie and Devereux that Shaw would've known he was in financial trouble roughly a year ago, before he "invested" Lester's savings for him.
- Executive Excess: Shaw enjoyed such luxuries as a penthouse apartment and brie cheese in his burgers. This becomes Played for Drama, when it was revealed he knowingly splurged the Tower employees' pensions on luxuries even when he knew his con was ending to maintain appearances.
- Explain, Explain... Oh, Crap!: Charlie is recounting the wild goose chase that ensued after Enrique sent a text from his wife's stolen phone saying that her water broke. He trails off, then asks, "Have you seen Josh?"
- Exposition Cut: Josh's morning routine introduces the main characters and their roles in the Tower.
- Expy: The Tower is a stand-in to the Trump International Hotel and Tower, where the movie was filmed at.note
- Extreme Doormat: Deconstructed. Claire accuses Josh of avoiding confrontation, yet he explains he's only that way because he has no need to be otherwise. Then he hears about Lester...
- Face–Heel Turn: Played with, per se. While planning for the heist, Charlie is hired to become the Tower's new manager. He promises to foil Josh's plans should he push through with the heist. Also, during the heist, Slide decides to go straight for the vault due to the skills he picked up from Odessa. Both of them manage to go through with the original group though.
- A Father to His Men: Josh towards his staff at the Tower, given his reaction to Shaw cheating them.
- Faux Affably Evil: Arthur Shaw seems like a nice guy at first, but as the movie goes on it shows that his kindness is all an act. Special mention should go to him "agreeing" to drop the charges against Josh for attacking his car in exchange for an apology, before taunting him about his dismissal and making a comment about doormen only shortly after Lester's dismissal, before revealing later he plans to sue him the first chance he gets, then telling Claire he plans to go after her badge for arresting him, right while offering to take her out for dinner.
- Five-Finger Discount: Slide asks Josh, Charlie, Enrique, and Fitzhugh to shoplift $50 worth of goods from the mall in order to prove that they are capable of pulling off a $20 million heist.
- Friendly Enemy: While Claire must arrest Josh for his stealing, he has no beef with him and even enjoys him smashing up Shaw's Ferrari. She even manages to get Josh a lenient sentence.
- The Ghost: Fitzhugh's wife and kids never appear onscreen.
- Guilt by Association Gag: When Josh smashes the windows of Arthur Shaw's car, Mr. Simon not only fires him for that but he also fires Charlie and Enrique, who were with Josh at the time. Mr. Simon doesn't care about the fact they didn't do anything (to be fair, Enrique did cheer Josh on).
- Gut Punch: Lester's suicide attempt over Shaw bilking him out of his retirement money reveal how utterly soulless Shaw is, especially when he shows zero remorse over his greed.
- Hollywood Density: A car made of pure gold being relatively easily moved and pushed by the cast, and most egregious example, the weight of the boxes containing the spare parts at the end seem to change as they are transferred from hand to hand.
- Insistent Terminology: When Claire took part of the footage of Josh hitting Shaw's car, it wasn't larceny, she "misplaced 3 minutes of footage".
- Interservice Rivalry: The policeman who isn't letting several FBI agents escort a man under house arrest back to his home. It would not have been much for him to go out and quickly allow six people to cross the parade route between balloons, but the plot demands it.
- Ironic Echo:
- "I'm sorry sir, but we don't accept tips at The Tower."
- "Checkmate." Bonus points for having the second quote come immediately after the first.
- Irony: Charlie compares Josh to Robin Hood but doesn't know who Friar Tuck is.
- Jerkass:
- Shaw turns out to be a pompous, arrogant figure who thinks he can get away with anything.
- Slide is fairly abrasive, though he's at least somewhat likable.
- Just Like Robin Hood: Josh doesn't even care about getting back the money that was stolen from him. His goal is to make sure everyone else who got scammed gets compensated, even at the risk of going to prison himself. Lampshaded as Charlie compares Josh to Robin Hood.
- Karmic Thief: The thieves target a dishonest Wall Street banker.
- Laser-Guided Karma: Mr. Simon for unjustly firing Charlie and Enrique when Josh only acted out of order and he eventually ended up imprisoned in a closet by Slide when the latter deviates from the heist. Granted, he gave Josh’s old job to Charlie, showing that he must’ve wanted to make up for unjustly firing him, but since he did not offer Enrique any compensation, this trope is semi-justified.
- Loophole Abuse: Averted. Shaw still has to go to jail for the hidden safe he didn't report, regardless if it is empty.
- "Metaphor" Is My Middle Name: When Claire uses the word "badass" to describe what Josh did to Shaw's car, Josh says "badass" is his middle name. Having checked his records, Clair says it's "Marvin".
- Misplaced-Names Poster: As you can see above, the names don't match up, and adding to that there are six names and seven people.
- The Mole: Lester, Manuel, and several other members of the staff are shown to be aware of the heist as it goes on.
- Mood Whiplash: Often, after a serious scene, the scene (thanks to context) will cut to things like the inside of a Toys R Us where a My Little Pony (G3, no less!) ferris wheel cart can be seen, or the SpongeBob SquarePants theme song.
- Motor Mouth: Slide. It's Eddie Murphy, so it's pretty much a given.
- Never Trust a Trailer: The trailers and promotional material lead Claire Denham, Tea Leoni's character, to be a member of the heist crew. She is an FBI Agent assigned to keep watch of Shaw and serves as Josh's (Ben Stiller) love interest. The trailer also makes it look like Odessa will make a Face–Heel Turn. In the movie, she was just disappointed that the guard was allergic to chocolate. Plus, it makes Stiller and Murphy look like co-leads, when Slide is actually a supporting role.
- No Celebrities Were Harmed: Shaw, with his decades-long Ponzi scheme and extravagant lifestyle, refers to Bernie Madoff.
- The movie originated as a story of former Trump Tower employees pulling a heist to get revenge on Donald Trump. Scenes were even filmed at Trump Tower itself.
- No Good Deed Goes Unpunished: It happens to Josh twice.
- After he learns of Lester’s attempted suicide, he decides to avenge Lester by vandalizing Shawn’s Ferrari with a golf club. This leads to him being fired by Mr. Simon.
- Then Josh’s plans the heist to rob Shaw’s penthouse. While it does provide the FBI with the evidence they need to put Shaw away for life, and the team uses the gold from Shaw’s Ferrari to help Lester and the other employees of The Tower to cover their losses, Josh being the mastermind behind the robbery has to spend two years in prison. Josh doesn’t mind though, as he knows his sentence isn’t as long as Shaw’s and he satisfied he made Shaw pay for what he’s done.
- No Name Given: Mr. Fitzhugh's first name is never revealed.
- Noodle Incident: Charlie references how he drove Paul McCartney from the Tower because he thought "wanker" was a compliment.
- No Peripheral Vision: Thousands of people in the parade fail to notice a bright red Ferrari being dangled off the side of a building. They are really concentrating on that parade.
- Oblivious Janitor Cut: A maid wearing headphones while vacuuming an apartment fails to notice the Ferrari being lowered outside the window behind her.
- Off the Rails: After all the build-up and planning, the gang ends up sending the heist flying off the rails in the first two minutes.
- Oh, Crap!: Shaw is reduced to begging when Josh reveals that they found his ledger of all his criminal accounts and are going to present it to the authorities.
- Once Done, Never Forgotten: Josh has to bring up his childhood asthma before Slide remembers him as the kid at daycare who had fits that got labeled as seizures. Afterwards, Slide isn't afraid to make fun of Josh for being "seizure boy".
- Only Known by Their Nickname: Slide's real name (Darnell) is only mentioned once in the entire film. During the brief time he interacts with Mr. Simon, the latter calls him "Mr. Davis".
- Pay Evil unto Evil: After Josh learns of how Lester attempted to commit suicide, due to Shaw taking all of Lester's life savings, he decides to use a golf club to vandalize Shaw's prized car in the penthouse in retaliation for Lester. Although, this leads to him getting fired along with Charlie and Enrique.
- The Precious, Precious Car: Oh, quite precious, as we discover it's made of gold and, according to Mr. Fitzhugh, it's worth between 40 and 50 million dollars.
- Reasonable Authority Figure: FBI Director Mazin is committed to putting Shaw away and is willing to make a fair deal with the heroes to get that, but at the same time won't let their theft go completely unpunished.
- Rule of Three:
- Mrs. Hightower returns from her trip to Cairo three days earlier than expected.
- Not believing Josh's excuse for Charlie to be absent, Mr. Simon tells Josh Charlie has three minutes to show up for work.
- Enrique Dev'reaux worked at Burger King for the last three years before being hired to work at The Tower.
- Mr. Fitzhugh says he'd live in his car but it's been repossessed three months ago.
- Lester's work experience includes 3 years at the Pierre.
- Three people confront Shaw about taking Lester's savings: Josh, Charlie and Enrique.
- Claire Denham tells Josh that Shaw took 20 millions from his accounts three months ago and that Josh broke three federal laws when he damaged Shaw's car.
- Claire "misplaced 3 minutes of footage" of Charlie vandalizing Shaw's car.
- When Ms. Iovenko introduces herself as Josh's lawyer, she says she passed the bar exam three days ago.
- Sassy Black Woman: Odessa. Bonus points for being Jamaican...
- Secret Test of Character: During Josh's confrontation with Shaw in the latter's penthouse, Josh makes a small one of these by informing Shaw of Lester's suicide attempt and asking whether or not Shaw really cares about Lester. Despite Shaw's concern upon learning of the ordeal and his insistence that Lester has been an important part of his life for years, Shaw fails this because he never bothered to ask whether Lester is alive or dead.
- Screw the Money, I Have Rules!: Upon learning Josh and his crew found the ledger, Shaw tries to bribe them but they remind him they "don't accept tips at The Tower".
- Shaped Like Itself:
- Don't make Slide mad or he'll "blow your face clean off your face."
- The tower named, well, The Tower.
- Sir Swears-a-Lot: Slide regularly includes expletives in his vocabulary.
- Smart People Play Chess: Josh and Shaw. They play one another online at the beginning of the film, and apparently they've been doing so for a while.
- Smug Snake: When Arthur Shaw is confronted over the missing funds he misappropriated, he reveals himself to be a pompous, arrogant snob who thinks he can get away with anything. He maintains his arrogance until Josh reveals his intentions to use Shaw's own ledger as evidence against him, reducing him to begging.
- Soul Brotha: Slide is an affectionate parody of stock hoodlums of African descent. In a slight variation, Slide is a burglar as opposed to a street mugger, and is unfamiliar with the art of safe-cracking.
- Surprisingly Realistic Outcome: Josh smashing Shaw's Ferrari, while well-deserved, gets him fired by Mr. Simon and threatened with a lawsuit by Shaw himself. No matter how righteous your vengeance is, you can still be punished for acting like a vigilante.
- Surveillance Station Slacker: Manuel reads magazines instead of watching the security cameras.
- Taking You with Me: At the end of the film, Josh ensures Shaw's downfall alongside his own by handing the FBI the latter's ledger containing enough evidence to lock Shaw away for the rest of his life, accepting a reduced sentence for himself and enabling the rest of the heist team to walk free.
- Thanksgiving Day Story: The eponymous heist takes place during Macy's Thanksgiving Day Parade.
- Uncommon Time: Much of Christophe Beck's score is in 7/8.
- Unusually Uninteresting Sight: Mrs. Cronan doesn't care that she just saw a car inside a building's corridor.
- Unwanted Assistance: After Josh gets his friends fired.
- Unwanted Rescue: Josh helps stop several men who are spiriting Shaw away in their car, only to find out it was an attempt to flee justice and not a kidnapping.
- Villain with Good Publicity: Before news of his crimes come out, Shaw seems like a nice guy, having friendly chats with lowly members of staff and playing regular chess games with Josh. He then abuses their trust to get them to give him their money.
- What Happened to the Mouse?: Last we saw of Mr. Simon, he was still locked in the closet.
- White Bread and Black Brotha: In order to get revenge on Shaw for defrauding him and his employees, Josh tracks down Slide, his black childhood friend who's since become a petty thief and carjacker, to plan the heist.
- Xanatos Speed Chess: Josh establishes himself as a master of thinking on his feet, shown when the crew discovers the safe empty, only to discover the gold Ferrari, with Josh altering the plan accordingly by hiding the car in the elevator shaft, later the pool. Josh also ensures that Shaw doesn't remain unscathed in the aftermath of the heist, accepting a shorter jail sentence in exchange for the ledger containing evidence of Shaw's fraudulent activities, ultimately putting Shaw away for life.
