Completed during "Home Sweet Home", after delivering a Walter Coupe to Mike.

Completed during "Home Sweet Home" by defeating a debt collector (who harasses Francesca) in a fistfight.

This achievement is available during "Home Sweet Home", when the player heads to Joe Barbaro's apartment for the first time in the storyline; both the woman and her spouse are found beside a black broken down Shubert 38 on the right side of the road towards Joe's apartment, across the street from the block where the Scaletta apartment is. After an argument that sends the woman's husband walking away in irritation, the player may offer help to the woman; by fixing the car, the achievement is unlocked.

This is possible only after the player deactivates the alarm system on the basement level of the Office of Price Administration, accessible through the west side of the lobby, while preventing the guards from responding violently towards the player.

Achievable during "The Professional", when the player must deliver six gas stamps to any of Empire Bay's gas stations within an allocated time

A mission in "Our Good Friend", the objective is to avoid Henry from stumbling across both Vito and Leo in Leo's mansion. This achievement is possible by climbing out through a northeastern balcony on the second floor, after obtaining sheets from a room on the northwestern side of the mansion (next to a bathroom).

Completing Chapter 15 earns the player this achievement.

This achievement is typically possible only when driving sports cars that have received two levels of upgrade. The highway on the western riverside edge of Empire Bay's east side, being long and straight, is ideal for this achievement.

Cars stored in garages and used repeatedly during missions are ideal for this achievement.

The ability to crush cars is available after meeting Mike for the first time during "Home Sweet Home" and remains for the remainder of the mission.

The ability to sell cars is only available between the time the player sells a Greaser car during "The Wild Ones" and the start of "Stairway to Heaven" (regardless of whether or not the player can skip doing Derek job during the mission).

This is usually possible by driving along the highways of Empire Bay, where tight corners are scarce. It is also advisable to drive just over the required speed in order to delay the inevitability of running out of highway.

This achievement is usually possible when the player robs stores located within close proximity to one another, which helps to reduce traveling time.

The simple act of buying a suit from Vangel's unlocks this achievement.

Achieved by selecting the "basic tuning" option at any Body Shop.

The maximum vehicle upgrade is "sports tuning", which is only available beginning "In Loving Memory of Francesco Potenza", when the player unlocks new Body Shop options.

The requirement is to stay alive for the allocated time while on a level 3 or 4 wanted level, during which the police open fire at the player. Preferrably done while in a Shubert Armored Truck.

Includes any Playboy magazine or wanted poster

Achieved during "Enemy of the State", when the player is tasked by Derek to extort protection money from the dockworkers (in other words, "paying the barber" for their "haircuts"). By defeating one of the dockworkers who opposes aggressively, the player completes the achievement.

Achievable in the beginning of "The Buzzsaw", when Gina, "Joe's girl" is met with a minor car accident with a raging hoodlum just outside Joe's apartment as the player exits the building; by intervening and defeating the gangster in a fistfight, the achievement is complete. Note that the player must interact with the duo before their scripted sequence ends, to which point the two simply walk back to their car and drive away.

Achievable during the later portion of "Room Service", after Joe accidentally kills a Lone Star bartender while drunk. The achievement is completed when the player successfully disposes the bartender's body (which is chucked in the trunk of his car) using Mike's car crusher at his junkyard.

Available near the end of "A Friend of Ours" by raiding the Hill of Tara bar; the player must kill the escaping Mickey Desmond.

Achievable early in "Stairway to Heaven", by killing a character from the original Mafia.

Achievable during "Stairway to Heaven" by killing Derek during the dockworker strike. Note that it is possible to avoid this achievement when the player already has adequate cash to skip working with Derek.

PlayStation 3 achievement only.