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  • Whenever you survive an assault wave without anyone getting downed. The higher the difficulty, the more awesome the moment.
    Bain: They weren't expecting that for god damn sure!
    Bain: Gonna be a lot of early retirement forms filed today!
  • The Big Bank heist. From the trailer to the heist itself.
  • Day 2 of the Firestarter heist has the crew go to an auxiliary FBI building and sneak inside to steal a server. Yes, you get to stage a heist on the freaking FBI.
  • Bain might be the epitome of Affably Evil when it comes to his interactions with the PAYDAY Gang and his Crime.Net contacts, but make no mistake— he's not a man you ever want to truly piss off, especially if he's paying you. To drive this point home, one rare random event during GO Bank (the Plan B route), has him go ballistic when the pilot he's hired to evacuate the loot balks at using the bank's roof as a pickup point for the fulton skyhook, making it VERY clear to the pilot what will happen to him if he dares to disobey— successfully making the pilot obey his orders for the rest of the heist without further complaint.
    Bain: Do as you're told, goddamn it! I can shut down every airport for a thousand miles and have you ditched in the ocean, you spineless turd. Over.
    Bain: This isn't a request. Get your ass into position for a roof pick-up, or I'll see whole squadrons of F-16's scrambled in your direction!
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  • Provided you're a capable crew, pulling off a Death Wish or a Death Sentencenote  heist qualifies, especially if it's multi-day. It's one thing to win on OVERKILL mode, but to take it further and win when the the odds are deliberately stacked against you and computer is taking ludicrous liberties (e.g. blowing the Rats: Day 1 meth lab nukes the map) can feel pretty damn fantastic.
  • The Death Wish trailer itself, which features an LMG reloading battle between Chains and a Bulldozer to the muted part of the eponymous track Death Wish, the music reaching a crescendo as they load and lock a new box mag. There are no character voices - it's all in-engine and all power.
  • The new Crime Spree game mode has players performing heist after heist, with the cops steadily getting stronger and deadlier (including Captain Winters shields appearing on a regular basis, Medic Dozers, Minigun Dozers, and much, much more). Some players have managed to reach over 50,000 in this game mode, at which point literally every enemy is Made of Iron and almost immediately lethal.
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  • With the Hoxton Breakout heist now playable, we get a second raid on the FBI as Day 2 of said heist. No quiet option for this one, though. Good thing they left the keycards to their infirmary and armoury out in the open, eh?...
  • PAYDAY 2: A Merry Payday Christmas features Old Hoxton performing heist-themed Christmassy songs. It also has an intro track, where Old Hoxton is verified for the Badass he is while trying to get his lawyer to bust him out.
    Old Hoxton: You need some... economic... motivation?
    Lawyer: Look, I'm gonna pretend I didn't hear that.
    Old Hoxton: Ah, you prefer a whip to a carrot.
    Lawyer: This conversation is over.
    Old Hoxton: This conversation's over when I say it's over!

    Then not a few seconds later...

    Old Hoxton: I guess I need to contact Bain.
    Lawyer: Who's... Bain?
    Old Hoxton: This conversation IS over.
    • Moreso, on a meta-level, the whole album served as an early announcement that the Hoxton Breakout heist had begun development.
  • Plan C of the Election Day heist once again shows how far ahead Bain thinks. To keep suspicion off of the Elephant for rigging the voting process, you have to wreck the voting machines. Before that, Bain has you scramble the database that contains the votes so that there won't be any back up data. You then blow a hole in a wall to access a bank next door, which not only destroys the voting machines, but the plan also has you also robbing the bank so the cops think you just went through the first building to rob the place next door rather than tampering with votes.
  • Getting all the bags in Rats on Death Wish or Death Sentence. This involves cooking every bag of meth, getting the money from the gang AND stealing the meth back, and then getting all of the money from the transport and getting it into the helicopter. Any team who can pull this off has earned themselves a place in the Heister Hall Of Fame.
    • Similarly, beating the world record for bags looted in the Xmas Heist.
  • Fans have been waiting for the Hoxton Breakout heist, and it has proven to be Worth It:
    • Day 1 goes almost exactly as depicted in the trailer, starting with the crew blowing up the wall beside Hoxton and his two guards. They escort him to the pickup, only it's armoured up now and the crew have to work their way through the blockaded streets to the parking garage, dealing with road hazards and wave upon wave of police as they go. Upon reaching the garage, the crew has to locate and hack the computer within to drop the bollards on the ramp to get to the other end of the garage, where they remove the armour from the pickup for a speedy getaway.
    • Day 2 sees Hoxton instruct the crew to literally attack the FBI head on, by getting the driver to ram his way into their front office. Within, Hoxton hacks into their database in order to find out who the informant was that ratted out Hoxton to the Feds, done in four parts with the police still sending wave after wave of officers against you. With map-provided medkits and ammo thanks to the FBI's own private medical room and armoury, this is one massive gunfight spread all over the building, with the crew running various errands for Hoxton to help him get the information he needs. Finally, the crew pulls a server from the computer with all the info Hoxton has found on it, and legs it back to the getaway driver who's found a set of FBI wheels for you to escape in.
      • It's not just any FBI building, either. It's FBI Headquarters.
      • The kicker? As of this moment (November 3rd, 2014), this is the best paying heist in the game by a wide margin. Even on Normal, you can expect to get at least 1 million. There's also a Pro version, which pays even better.
      • This is despite the heist having absolutely no optional bag loot, only having a single server when it comes to mission bags. This makes the mission much more single-player friendly.
      • There can sometimes be a male NPC in a classy suit in the Director's Office, which is open instead of locked like most other rooms... that's right, you can not only hack the FBI Director's computer, you can also take him hostage. Or shoot him.
  • For all the fans of Hotline Miami, as well as its associated heist: Do you know what time it is?
  • The Car Shop Heist. You have to steal some fancy cars. Sounds simple enough, but how do you move a car in a game where driving was never a game mechanic? It's a mechanic now for the very first time. Once you get the keys for the cars, you get to drive the cars out of the shop through the windows and blaze through the tunnels before reaching the docks and parking the cars in the containers to be shipped out.
  • Overkill managed to pull one on nearly the entire community with Hoxton's Revenge - The Rat was NONE of the obvious suspects, but with a little hindsight and digging still makes perfect sense.
  • The heist dealing with the Rat himself. Going in quietly means you get to kill the Rat without him becoming none the wiser and steal evidence that is incriminating to the crew. Not only does the quiet method lets the crew get their revenge without alerting anybody, but it also makes the FBI look grossly inept at their jobs since their valued informant just got killed right under their noses. If you choose to do the job loud (or get caught early during stealth), you get to storm the place and drill into the panic room as you listen to the Rat fruitlessly taunt you before you kill him once the door opens. Either way, Hoxton is getting the revenge he deserves.
  • Any of the live-action sequences when one of the gang is saving one or more of the others' respective sorry carcasses (Wolf gets special mention for drilling some new holes into a Dozer). Or in-game, for that matter, since one of the most important core skills a good group needs is the ability to save each other's butts at a moment's notice. Probably doubles for what passes for a Heartwarming Moment for this series too.
  • The Point Break Heists both add awesome moments to the game. In Birth of Sky, the crew hide in a compartment, burst out, shoot through a plane full of mercenaries, dump huge pallets of money out of the plane, and then the mission gets to live up to its name when the team follows, skydiving.
  • The other Point Break Heist, Under The Mountain, is more of a meatgrinder. Then the crew exits on the side of a mountain to disable a radar dish and you get a good enough view to realize you just robbed a mercenary-controlled Cold War bunker that looks like something out of James Bond.
  • In celebration of the game receiving its 100th update, Overkill announced that they severed all ties with 505 Games and that Starbreeze, Overkill's parent company, had purchased full rights to the PAYDAY franchise, meaning the developers are no longer under the whim of 505's Executive Meddling (which was the reason why the game had so much DLC and microtransactions). To further sweeten the news, the devs also announced that all safes released from now on can be unlocked for free without the need of a drill while all the old safes still need a drill. For the massive flop Overkill made, the news of the developers ditching their publishers that pushed the microtransactions and the cheap DLC was welcome to hear. And even on top of that Starbreeze announced that there's plans to support PAYDAY 2 for another 18 months and given the details of the purchasing agreement with 505 PAYDAY 3 was indirectly referenced to being a thing in the works.
  • On June 13, they announced the next pair of DLC for the game; a 2-day heist and a new character. Said character is a biker named Rust, and is being played by Ron Perlman.
    • And said two-day heist culminates in stealing a device off of a train. No, not a stationary one conveniently parked like so many times before; we're talking a Western-style shootout leaping between moving train cars while helicopters and SWAT trucks swoop in to shoot you down.
  • On December 12, another pair of DLC was announced of a new playable character and heist. The new character? None other than Tony Montana. That's right, Scarface himself is now a member of the PAYDAY crew. The new heist? Hitting Montana's manor to assassinate Ernesto Sosa, nephew of the Big Bad of the film. And yes, Tony comes with an assault rifle with grenade launcher that's named "Little Friend".
    • Ernesto gets his own if you break in on loud, as he replicates Tony's Last Villain Stand from that film.
  • The PAYDAY: Crime War trailer, which features a playable PAYDAY Gang-Expy law enforcement ready to take down the gang all by themselves, PvP mode and of course, even the cops can use masks. The ending features Dallas' and Wolf's masks getting blasted in the air with bullet holes. And the message at the end of the trailer? "Keep those masks flying!"
  • The Henry's Rock heist has to count for something in context, considering you're going to the very heart of Murkywater itself, swarming with veritable armies of both your usual adversaries and PMC goons, where some of the world's most powerful secrets and valuable treasures are held in absolute secret, and raiding it for two of its most prized relics. It's a little like robbing Area 51 for alien tech, just as difficult, and about as rewarding when it's all said and done.
  • Meta example: The community, despite having been shaved down immensely, still managed to solve each component of the Beyond Yesterday Alternate Reality Game in less than a day after each encryption showed up. What makes this even more stunning is that the decryption keys are very obscure (for example, Garrett's reply is encoded with a key referring to a very specific number related to the second in units of time, minus ten, the amendments in the Bill of Rights) - meaning that some ridiculously proficient detective work was being done in the process.
  • Hell's Island. It may not be Alcatraz, but it may well be it, plus, you're breaking out Bain, who promptly goes on a rampage once he's released from his cell, massacring every Murky unfortunate enough to be in his way.
  • The Grand Finale. The "greatest heist of all", that Bain has been preparing the crew for for the past seven years, finally comes to fruition. With Bain on his deathbed, he orders the crew to rob The White House. What are they stealing? Presidential pardons with no names attached. By stealing pardons, they can scribble their names on them and can finally be free from the law forever! Go for the stealth route and you'll pull off a heist directly in the heart of the nation with the toughest security known and no one would even know you were there. Go loud and you basically have done what no other criminal could have hoped to achieve; turning the White House into a war zone, stealing the pardons, and surviving.
  • The True Ending. After certain requirements are met, the gang ends up finding a hidden vault underneath the White House. After managing to solve its puzzle, all the while being bombarded by literal demon Cloakers, and finding a strange device within, the Dentist arrives with a captured Bain and Locke, bringing Mayan gold and threatening to kill them both. Sounds bad, right? Well, he's alone, and doesn't make any attempt to cover himself, and afterwards, if you manage to put the gold in quick enough, it unlocks... well, the True Ending, where most of the gang successfully retires. How? Well, the device in the vault seemingly reincarnates Bain as...the motherfucking President. Bain basically steals the entirety of the United States. The Greatest Heist of All, indeed.
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