These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Anvilicious: The game can be pretty blatant about its moral stance on Mafia activities. Many characters you work with are repugnant, and you never get to enjoy the luxuries that crime affords for very long before something takes them away. The game can even be seen as a Shoot the Shaggy Dog story.
Of special note is the stance against drug-dealing. Just about every character associated with drugs dies at some point, with Vito being the sole exception perhaps because he only reluctantly agrees to deal drugs due to losing everything he had shortly before then. It's noteworthy that the only mob boss that doesn't die is Vinci, who has a strong distaste for drug-dealing unlike the other bosses.
The licensed tracks are pretty good though, particularly the scripted ones (see Suspiciously Appropo Music)
Bolivian Army Ending: The ending of the game is ambiguous enough that it's unclear who exactly lives and dies. The game seems to imply that Joe dies but Vito lives, but it's also entirely possible that Joe and Vito would survive to take on the remnants of the Vinci family after already previously severely wounding the others. It's also entirely possible that the game has an outright Downer Ending where Joe and Vito have outlived their usefulness to the Vinci family, with the two of them being unceremoniously killed so the Vincis can rise to power due to no real opposition anymore.
Darkness-Induced Audience Apathy: It can be hard to root for Vito to make his life a good living for him again, especially considering the fact that he happens to be a jerk who ended up in a gangster life.
He's Just Hiding: At the end of the game, it's heavily implied that Joe is killed. Of course, since we don't actually see the deed itself, a lot of people are convinced that Joe survives the events of the game, even though it was pretty clear that those guys weren't exactly taking him out for a nice night on the town.
However, Joe has proven himself both durable and able to win a fight, and considering that there were only two guys with him in the other car (one was the driver and one sat next to Joe), one could imagine that he could incapitate both fairly easy. At least he was armed when he entered the car...
Hilarious in Hindsight: An early mission where you have to stack crates in the back of a truck for a lousy 10 bucks. The mission ends with you saying screw it and informing your boss that you come for a better job. The kicker? Now you're sent out the office to collect cash from all of the employees in the warehouse, collecting 10 dollars from each. In other words: if you had completed the job you got offered first, you would've spent a lot of time earning only 10 bucks, only to lose it immediately.
That becomes a Cerebus Callback later on, when it's revealed that Derek killed Vito's father, because he took exception to Derek's Bad Boss ways.
Hype Backlash: While the game has received generally positive reviews, many have criticized it for its relatively short length (around 10 hours) and lack of things to do outside of missions, as compared to other sandbox games (the fact that a lot of features were Dummied Out didn't really help). So a lot of people, who were expecting something along the lines of Grand Theft Auto Rocks The 1950s, were let down.
Narm: Settle down Vito, we know your hyped up on adrenaline, but shut up about the barber already.
Nearly everything Jimmy says in the DLC.
Nightmare Fuel: Henry being brutally murdered by the Chinese... who are using meat cleavers. The worst part is hearing Henry, who has spent the game up to this point cool and in control, screaming and crying in agony.
The slaughterhouse in the mission "Ball and Beans" is quite disturbing, too - especially since you can hear pigs squealing as they are slaughtered.
Nintendo Hard: The Bomb Under the Seat mission in Joe's Adventures, to be specific. Expect a mother lode of irate players who bashed 2K for putting up an unbearable mission that involves driving a car to a specific location, all while under time pressure, traffic, winding roads and with the threat of a bomb exploding if you go too slow.
Only The Creator Does It Right: Many fans of the original Mafia dislike the game particularly because very few of the original staff were on its devteam, and most of them left during production.
Porting Disaster: Take 2 has apologized for making the PlayStation 3 version of Mafia II the least feature rich version, compared to the PC (which is the fullest experience) and Xbox 360 versions.
Tear Jerker: When Vito finds out that his mother has died - while he's in prison, no less, and Marty's death - especially Joe's reaction.
Killing Tommy Angelo from the first game, Henry dying horribly at the hands of the Chinese (because he was feeding info to the Feds - putting him in a Tommy Angelo situation), and Joe likely getting killed at the end.
The pause screen music.
That One Level: The dockworker strike level. Enjoy the insanely bad checkpoints.
"Enemy of the State". You start off doing a stealth mission, which ends badly regardless of what you do. The entrance is swarming with cops and you have to escape the way you came in from, out of a bathroom window, likely with cops shooting at you the whole while. Wanted, you have to evade more police and get back to Henry. Oh, but what's this?! The tickets you stole expire at midnight! Hurry and deposit them at gas stations before the time limit ends. Said time limit continues even as your character has an unskippable conversation with the attendants. They won't talk to you if you are wanted, which you probably will be because you have to speed if you want to make it. Finally, as icing on the cake, you can't kill anyone or you forfeit a bonus.
You can turn off the alarm in the basement and get out of a window on the second floor.You also lose the bonus if you alarm the cops and not just killing anybody.
"Fix The Fixers" from the Betrayal of Jimmy DLC. Up until this point the difficulty of the Triad plotline missions have been tough, but forgiving. Here the difficulty ramps way up. You're tasked to kill three minibosses in a sprawling warehouse complex. Three guys with obscene amounts of health and plenty of backup. The regular Triad goons are armed to the teeth with automatic weapons rivaling your own arsenal, have pinpoint accuracy and can hit you from halfway across the area, and are posted around every corner and rooftop. Oh, and did I mention the obscene health on the minibosses? You'd better be good at scoring headshots, because these guys won't go down even after dumping a Tommy gun into them. For added fun, the cops will happily join in and the wanted meter will freak out, clearing inside the mission area one second, cops training their guns on you the next.
"In Loving Memory of Francesco Potenza". You literally have only one autosave in the whole chapter, so you better have free time when you play it.