During the cut-scene before the mission "Boomshine Saigon", Phil gets his right arm blown off. However, at the end of the mission when Tommy drops him off at the hospital, Phil's left arm is gone instead.
In the Mission "Two Bit Hit", the game tells you to drive to the clothes shop "Rafael's", but the store the game leads you to is called "Little Havana Streetwear & Tattoo Parlour".
When you look out through the main door of the mansion on Starfish Island, there's a pillar right outside the door. It's the pillar from one of the equally spaced arches supporting the overhanging upper floor. But when you get outside and look back towards the door, there is no pillar. The arch in front of the door is a double span arch.
During one of The Malibu asset missions, Ken tells Tommy he got the chalkboard he had asked for. If you go to the upstairs office of the Malibu, you will see a map of the bank drawn on it. This means that Tommy wanted to use it for instructions on robbing that bank. However, if you go to the office in the beginning or at any time before Tommy actually buys the club, you can still see it there.
At the end of the mission: The Job they return to Cam's Cannery and split up the money. Mercedes is there and offers to give Tommy a message. Then immediately after Kent Paul pipes up about needing more money for clothes. Then after completing the game Tommy receives phone calls from different characters. One of these is Paul saying that he met a street walker. "Said her name was Mercedes or something like that." But they should have known each other from after The Job. They were in the same room.
When Tommy shoots the revolver, shells can be seen coming out of the gun as if it's semiautomatic.
The M1911 is shown as having a 17-round magazine capacity, way above its actual magazine capacity of 7.
William Fichtner is wrongly spelled as Willian Fichtner during the end credits.
When people drown, they are shown with their torso parallel with the water surface, legs and arms dangling. In reality, your legs will float up to the surface so they are horizontal. Only if you make a conscious effort would you be able to keep your legs vertical.
The song "Añung Añunga" is incorrectly listed as "Agaunile" in the game manual.
When the limo for Avery's missions pulls up, you can clearly see there's nobody in there.
When looking at a passenger in a car, when they speak, their lips do not move.
In the upstairs office of the Malibu Club, there is a model of Cortez' yacht in front of a large mirror. The entire room can be seen reflected in the mirror, yet you can't see Tommy even when he's standing right in front of it.
There is a loading screen depicting Auntie Poulet in front of a sign reading "Havana". Since Auntie Poulet is the leader of the Haitian gang, the sign should read "Haiti" or "Port-Au-Prince", as Port-Au-Prince is the capital of Haiti, as Havana is the capital of Cuba.
In the missions "Four Iron", "Demolition Man" and "Two Bit Hit", Avery Carrington's stretch-limousine accelerates and slows down - but there is no driver on the driver's seat. In addition, Avery himself isn't inside.
One of the assault rifles appears as an "M4" in the game, but the M4 wasn't developed until 1994. On the other hand, the gun more closely resembles CAR-15 which would be more accurate within the time period
The song "A Gozar Con Mi Combo" by Cachao, which can be heard on Radio Espantoso, was released in 1994, 8 years after the game takes place.
VCPD officers are using automatic pistols; in 1986 the vast majority of policemen in the U.S. were still using revolvers.
During the "Keep your friends close..." mission intro, Tommy says to load 20 million into briefcases, while the subtitles say 3 million. In a later cut scene, both the subtitles and the audio say, "Here is your three million".
This goof was discovered in the XBOX version of the game: In one of the early Ken Rosenberg missions, the cinema scene shows Tommy enter Rosenberg's office with Rosenberg fast asleep on the couch. Tommy then slams the door, scaring Rosenberg awake and apparently causing Rosenberg to defecate himself. However, the sound of the door slam and most of the dialogue that follows is at least one second behind the corresponding visual.
During the cut-scene for the mission "Cop Land", Mike's lips don't move when talking.
In the beta version of the game, Fort Baxter Air Base was going to be larger, and have its own runway and communications tower. However, they removed this from the final game, but in the view from the other island (when you are not on the island the air base is located) you can still see the tower. When you enter the island, it disappears. Among fans of the series, the tower is known as 'The Ghost Tower'.
All the directional road signs are blue; in the U.S. they are green.
During the mission "Cabmageddon" Delores, the dispatcher, instructs Tommy to pick up Mercedes Cortez in Downtown. But the destination is the former Civil Asset Forfeiture Impound in Viceport.
The parking lot height sign at the Washington Mall gives the height in meters; the U.S. doesn't use the metric system.
The parking garage at the marina displays the height clearance in meters; the U.S. doesn't use the metric system.
After completing the mission "Keep Your Friends Close," you'll receive a phone call from film director Steve Scott, even if haven't already purchased Interglobal Studios.
During the cut-scene for the mission "Naval Engagement", Danny Trejo, the voice actor of Umberto Robina, mispronounces Umberto's last name as "Robino".
There are a few instances in cutscenes, where a character comments on the player wearing a certain outfit regardless of the outfit the player may be wearing. Such as Rosenberg in the last cutscene for "Keep Your Friends Close...", Umberto in the cutscene for "Stunt Boat Challenge, Big Mitch in the cutscene for "Alloy Wheels of Steel" and Jethro in the cutscene for buying the boatyard.