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  • Alternative Character Interpretation:
    • Donald Love didn't have much Character Development in III and Vice City, but he's really weird in this game. It raises a lot of questions on the motives he had in III and how well he was hiding his weirdness.
    • Toni Cipriani: A righteous man who delights in only committing atrocities because he is just following orders? Or is he a Psycho for Hire? Toni is probably the protagonist who committed the greatest atrocities in the GTA canon, including killing a man with an ax and carrying his remains to a butcher shop. Remember, this was done out of his own will and not to follow an order, not to mention several atrocities under Donald Love and Ned Burner's orders. While he still repents of his sins in a confessional, he is never shown seeking redemption when he bombed the area of Fort Staunton.
  • Base-Breaking Character: Donald Love is far more divisive in this game than he was in III. Some fans like his more flamboyant and outrageous character in this game and thought it gave him more of a personality, while others believe Love was completely ruined and preferred when he was a more suave and mysterious character.
  • Catharsis Factor:
    • After Vincenzo Cilli betrays you, killing him is very much worth it.
    • In multiplayer, Donald Love is available as a player skin, meaning he can be killed for all he's done through the story, bonus points if you are playing as Avery Carrington.
  • Complete Monster: Donald Love, a recurring character in the 3D Universe, is among its most depraved. Love presents himself as a charismatic, if eccentric, powerful businessman, arranging a gang war between the Yakuza and the Cartel just to lower property values. In this game it's revealed he is a self-indulgent cannibal, and implied sexual deviant. Aligning himself with the Leone Crime Family, Love runs in the race for mayor, sends protagonist Toni Cipriani out to murder his rival's campaigners and collect more bodies to feed on. Losing his fortune and campaign, Love makes plans to regain his fortune, starting by murdering his mentor, real-estate tycoon Avery Carrington, in order to steal his city development plans, later cannibalizing the body; and killing many people through the bombing of the heavily-populated Fort Staunton city district, just so he can make money off of redeveloping the district.
  • Game-Breaker: Selling scooters. There's a bike-selling minigame in the middle island, and once you've sold 10 of each 4 bike variantnote , you can replay the mission to sell infinite amounts of any bike. The "Faggio" is easily sold by driving around in small circles. Each 5 sold gives you 2500$ in addition to the previous reward. Repeat this long enough and eventually you'll start earning ridiculous amounts of money. It's even easier on the PSP, since you can just put the system in sleep mode if you get tired and continue later.
  • Game-Breaking Bug: Using cheats can possibly render the penultimate mission unwinnable, a conscious choice by the developers. Thankfully this bug can be prevented if Toni wears the Tuxedo jacket which automatically wears in the mission "A Date With Death" in order to rescue Toshiko Kasen.
  • Good Bad Bugs: With a lot of skill and practice, players can obtain a fully functional helicopter in two different missions, which can even be stored in your garage.
  • Harsher in Hindsight: Chronologically, Salvatore Leone's fate has been sealed when his uncle says "Every dog has its day." Yeah, about that...
  • Jerkass Woobie:
    • Salvatore Leone is a paranoid wreck of a Mafia Don in a strained relationship with his wife who later is barely rescued from an assassination attempt involving the crusher in the junkyard. He considers Toni to be the only person he can count on and even then his paranoia drives him to pull a gun on him before putting it down, shocked by his own actions.
    • Toni Cipriani too when you consider the verbal abuse he gets from his mother and his extreme reactions. Not to mention, in the game's backstory Toni was a high-ranking member of the Leones until he was forced to go into hiding in another country after performing a hit on a high-profile rival on Salvatore's orders. He returns to Liberty City only to find himself stripped of his rank and forced to work for Vincenzo Cilli who constantly disrespects him and has him perform increasingly dangerous jobs.
  • Jerks Are Worse Than Villains: While Massimo Torini is the ultimate Big Bad of the story, he has a lot of charm and does not really hold much of a grudge towards the Leones. Donald Love, for as despicable as he is, has several memorable hammy moments and antics. Even Vinnie manages to be quite an entertaining Hate Sink whose potential was not fully expanded. All three might be the villains of the story, yet they are not flat out hated by the players. The same cannot be said about Toni's mother, however. Her constant and ungrateful belittling of him goes too far, culminating in her sending hitmen to get rid of her own son. While she does change her mind after Toni officially becomes a Leone's member and call the hit off, this ultimately does not stick for long - come Grand Theft Auto III, she is back at bullying him, now with Toni himself forced to live in her restaurant and having to bear her at all times.
  • Magnificent Bastard: Massimo Torini is the Caporegime of the Sicilian Mafia, masterminding and overseeing their invasion of Liberty City after their tributes dried up. Despite his minimal appearances, almost every major conflict in the game is traced back to his manipulations. Ostensibly sent to relax tensions between the Leone, Forelli and Sindacco crime families, Torini secretly pushed the families against eachother; even reaching out to smaller gangs offering them a share, successfully driving Salvatore and Toni out of Portland. The following Mob War sees the Forellis' weakened, the Sindaccos’ wiped out, and the Leone's hanging by a thread when the Sicilian’s expose their ties to Donald Love, resulting in Salvatore’s arrest. When Torini learns that Salvatore’s charges may be overturned, he orders an audacious attack on the police convoy for the trial. When that fails, Torini personally kidnaps Mayor O’Donovan to keep him out of Salvatore’s reach. When cornered and confronted, Torini cordially explains that it was Nothing Personal, before nearly escaping.
  • Moral Event Horizon: See here.
  • Periphery Demographic: In some circles, Liberty City Stories was popular not for the game itself, but because it provided one of the easiest and most widely-used methods of jailbreaking the PSP to run homebrew software on it, via some trickery with the game's save system.
  • Porting Disaster:
    • Continuing the trend of mobile ports of GTA games being inferior to their console and PC counterparts, Liberty City Stories on iOS and Android is an extremely nasty port, because apart from having the same problems as the previous games, it also has very limited graphics settings & compatibility issues with some phones & tablets (particularly with Mali GPU devices), where the game refuses to work anywhere past the main menu. The fact that the port of Liberty City Stories was made by a different studio, Lucid Games, instead of the usual War Drum Studios/Grove Street Games, doesn't help. Possibly justified, considering this game was only released on the PlayStation Portable and PlayStation 2 beforehand.
    • Despite running on significantly more powerful hardware than the original PSP version, the PS2 version has several issues. For starters, it suffers from severe framerate issues that are present even on the digital PS3 version, meaning they're not caused by hardware limitations, but by some oddity in the game itself. The console version also introduces new glitches, such as the radio station sometimes glitching out and stopping playback until one reloads a save or restarts the console, and the credits sequence is also known for glitching out. That said, these problems can be overlooked with some patience, and the port is otherwise playable.
  • The Scrappy: As if she wasn't bad enough in GTA III, Maria is worse in this game. Some of Toni's problems are because of her screw-ups.
  • That One Level: See here.
  • That One Sidequest: The game ramps up the difficulty for obtaining some of the hidden packages to an almost insane level. One hidden package is located on top of a gas station roof in Portland is considered particularly difficult to reach, and even Guide Dang It! assistance is unhelpful. Another is located on a steel beam supporting the suspension bridge, only reachable by a perfectly-timed motorcycle jump.
  • They Wasted a Perfectly Good Character:
    • A common complaint about the game is that Massimo Torini, the Big Bad, doesn't really do that much and barely even appears. On the other hand, his dearth of appearances could have been used to make him more of a Walking Spoiler.
    • With the aforementioned complaint above, there are some who says that Vinnie would have been perfect to be the Big Bad considering his high rank in the Leones could make him a potential threat through a coup d'état like scenario where he tries to take over the Leones behind Toni and Salvatore’s back, or even betray them for the other gangs. His vendetta against Toni which was built up in the beginning of the game could also give personal stakes in the conflict, and his already Love to Hate status by the community shows he could also be a very entertaining villain.
    • Having Avery Carrington appear in a late game mission could have had lots of potential, but instead his role is reduced to an assassination target who does not even drop a single line of dialogue when you confront him, and is only used as a Deus ex Machina for Donald Love to propel back to glory.
  • Underused Game Mechanic: Considering you could steal helicopters & fly them in some missions, the lack of helicopters and/or rideable small planes in Francis International Airport is kind of glaring.

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