Dead to Rights/YMMV

Alternate Character Interpretation: Courtesy of Slowbeef.
Anticlimax Boss: Blanchov. After taking out his Dragon (in a much more epic gun battle), a cutscene activates showing Jack casually walking up to Blanchov and shooting him in the chest just once. After that, he dies. You don't even have to touch the controller.
Non Sequitur Scene: Longshoreman X. A hulking man armed with a crossbow who killed Gopher for no apparent reason.
- - Actually Longshoreman X is more of a Giant Space Flea From Nowhere
- Also Fahook getting drunk and shirtless in Level 14 because.....Uhhhh.....
  - It also doesn't help that his running animation is glitchy as hell.
Cliché Storm: Both the original game and Retribution, but in entirely different ways.
Follow the Leader: The original Dead to Rights was an attempt to copy Max Payne, with limited success. It was, in turn, followed by True Crime: Streets of LA, which actually had a superior take on the idea of a snarky cop on the edge who mixed martial arts with gunplay, but somehow less memorable overall.
- Retribution was a blatant copy of cover-shooters like Gears of War. It really just seems like the series tries to take all the best mechanics of current shooters, but gets everything wrong in development.
That One Boss: Three of them. Diggs, Fahook and Hennessey.
- You fight Diggs in a gas chamber. As the fight progresses, the gas slowly drains your health; you and Diggs take turns punching the mask off each other's faces and stealing it for air, which draws out a fight already stretched by Diggs' endurance.
- Fahook is fought in the back of a plane with limited cover. His gun will shred you to pieces if you're not careful, and you have to use the bullet time dive and the right weapons with precise timing in order to hit him before he hits you. Occasionally, Fahook will take a swig of a magic potion and start breathing health-bar-destroying fire at you (yes, really), at which point you have a limited window in which you have to shoot the potion out of his hands. To make matters worse, towards the end of the fight the back of the plane opens up, and you can get sucked out yourself if you aren't careful.
- Hennessey is even worse. He starts the first stage of the fight with an electrified riot shield which can kill you in a few hits, and will constantly charge at you, so you have to try and lure him into the water to short out his shield without getting hit yourself. After a few rounds of this, you have to fight off some more GAC squad mooks to reach the final melee fight with Hennessey. Hennessey has ridiculous endurance and will annihilate you in seconds if you haven't mastered your melee attacks. Fight back for a while and Hennessey opens up the door to the room's incinerator, then resumes his melee onslaught with his fists on fire. And at his last sliver of health, your melee-weary hands better be ready for a quick use of reflexes, because you'll have to knock him into the incinerator. Did we forget to mention there are no health pickups whatsoever during this fight?
  - The helicopter in the second game is also a real pain in the ass.
That One Level: The stripper minigame...
- Strike that, the entirety of the prison level, where you have to grind several different minigames to get enough cigarettes to bribe a guy for some stuff to escape prison. Later adaptations of the game made this skippable, at least.
  - Sure the prison level was a bit tedious, but it's NOTHING compared to the harbor level, which has one section with several snipers were you will very likely die dozens of times as there's virtually no cover and it's damn hard to find a position where you can kill the snipers without being shot yourself, and god help you if you wasted too much ammo in the beginning of the level, because then that section becomes a Luck-Based Mission.
    - I cast my vote on the return to the Construction Site. The fact that you wind up having to fight a chopper (again) doesn't help its case.
They Wasted a Perfectly Good Character: Patch. He's a suave assassin who has a fun character quick and a nice British accent, complete with memorable introduction. He does not have a single line after that, and proceeds to die as anticlimactically as possible.