Sergio Morello escapes no less than four assassination attempts. When Tommy gets relegated to simply keeping an eye out while "the professionals" handle their last one, they mess up again. Before Tommy gives chase, he reacts with:
The entire mission is finished with this gem of a line:
Tommy: You know what, boss?
Salieri: What?
Tommy: That's the first time I knocked someone off in their underpants.
Definitive Edition
When Paulie and Tommy are leaving to smash up Morello's vehicles, Tommy receives his first vehicle from Ralph... and it's a Bolt Ace, equivalent to the Ford Model T and just as slow and antiquated. Paulie is incredibly disappointed.
Paulie: I want to show you somethin' about the good life, and you're drivin' somethin' my Ma could've bought 20 years ago!
Characters in cars react to bumps, crashes and running over pedestrians, voicing their surprise. If story-related dialogue is cut off, the characters will speak their reaction voicelines, and then continue with something akin to "What was I saying again?".
During the run for Salieri's bar at the beginning of the game, you'll hear a man wonder where his date is, hoping that he got the correct location and time. Some running later, and you'll hear a woman a couple streets over angry that her date has failed to show up on time, possibly getting their meeting spot wrong. Again.
If you hang around there long enough, Tommy, despite being chased and shot at, will actually tell the woman where her date is. She even responds with a confused "thanks?".
The whole sequence is backed up by violins playing a jaunty tune. Not exactly the type of music you're thinking about when you're being chased by gun-toting gangsters.
He later returns as an old criminal associate of Herbert Baskerville's, hiding out in the safe of the Grand National Bank while wielding a shotgun... and still in his underwear. Killing him unlocks a clown outfit for Tommy to wear.
Sarah manages to fend off a couple of the assailants on her own, using a Groin Attack.
Paulie, now drunk and milling about, has to be found somewhere at the tracks during the victory party, and is taken home. He insists being taken to a brothel instead of his apartment. What's even funnier is that you can actually do this if you follow the description that he lays out, earning you the "Not Classy" achievement.
Dialogue as the driving goes on includes Paulie singing in Italian and complaining that he's being driven home instead of where he wants to go. And if you choose to go to Blue Tropics, Tommy says that he feels dirty just taking them there.
The remake changes Salvatore into speaking only Italian. Cue trouble between Tommy and Salvatore trying their best to communicate before the safe-cracking mission. They both know it's going to be a long night.
Shortly before they get into Salvatore's car, Tommy does his best to speak at least a little Italian to impress and please Salvatore.
Salvatore has to resort to some You No Take Candle with the limited English that he knows.
Tommy misunderstands Salvatore taking a break from the safe as him being done, tripping the alarm. Later, when they're in the clear for their escape, Salvatore unleashes an absolutely scathing rant in Italian against Tom for being so hot-headed. It's just to vent since he knows it's pretty much "like talking to [his] dog."
When Sergio Morello escapes the restaurant, Tommy decides to go after him on a nearby motorcycle. Paulie excitedly cheers him on, waving his Tommy gun in the air and crying out in a shrill voice like a child.
Sam and Paulie catch up to Sergio's car and join in the chase. However, Sam mistimes his driving and their car spins out, once again leaving Tommy to chase the lucky bastard on his own.
Paulie: What are you doing?! Nooo!
When the boys finally close in on Don Morello as he leaves the theater, a passing truck gets between them in the closer lane. Tommy brakes to a stop and waves the truck through, and then chases down Morello.
Gates, a bootlegger from Kentucky, has been facing physical abuse by Morello's gang and wants to defect to Salieri. He sports a broken nose during the meeting with him at the parking building, and Paulie wants to make the scene appear as though the operation was robbed. Paulie executes this plan by punching Gates in the face, catching everyone except Gates off-guard.
Gates: Damn thing's gonna be crooked by the time I'm done with this city!
Easter Eggs that have been added include an alien invasion and a set of objectives that you can complete to fend them off. You find notes around about abductions, then track down a UFO floating in the sky. After killing off some Mooks in alien-head costumes, you unlock a Men In Black-style suit.
Herbert Baskerville, the man who's been sending letters to Tommy in the Free Ride mode, turns out to have a German Shepherd's head. Yeah.
Perhaps unintentional, but the Game Over screen is headlined with "You Died", followed by the name of the mission below. When paired up with a few of the names, the results can be hilarious:
