"And it's always Once Upon a Time in New York City..."
- The opening number, "Once Upon A Time in New York City." Oliver is introduced as one of a litter of kittens in a cardboard box with a sign advertising them for sale. One by one, his brothers and sisters are adopted, the price on the sale sign gradually marked down until they're being given away for free... but by the end of the day, nobody has adopted Oliver. He's left alone in the box as night falls and it starts to rain, until the runoff from a drainpipe floods the box, collapses it, and nearly washes the poor kitten into a sewer drain. He's barely escaped from that when he's chased by a pack of feral dogs, and ends up huddling under the fender of a truck, terrified and alone. It's really quite impressive when the movie brings tears less than four minutes in!
- The scene in Sykes' lair when he sics his Right Hand Attack Dogs on Fagin and Dodger instantly leaps into battle to defend his master. When the No-Holds-Barred Beatdown is over, the way Fagin slowly approaches and kneels besides his loyal dog, sprawled motionless on the ground from the assault, is just heartbreaking. You can tell he's thinking, "That should've been me!" as he then glares back at Sykes as Sykes warns him the 12 hours he's been given might be his last 12 hours alive.
- After the gang "rescues" Oliver from Jenny, he explains she took him in and he requites her sentiment of being family to him. Dodger, hurt and rejected, explains the gang were his family and went to great lengths to help him, and coldly tells him to go back if he doesn't want to be with him (even Tito rather sheepishly suggests Dodger ease off a bit). Rita felt guilty as she was the one who figured out that Oliver was not kidnapped and was really happy being with Jenny, but went along with it anyway due to Georgette's insistence it was the opposite. She tells Dodger they never should've taken Oliver away, basically denying him a better life since he is still young and deserves better. Oliver takes one last heartbroken look at the saddened gang before starting to clamber away, before Fagin obliviously drags him back in.Oliver: I was happy there! Why'd you guys take me away?!
Einstein: We-We rescued you, Kitty. We brought you home.
Oliver: But I have another home now, and someone who loves me.
Dodger: What do ya mean, Kid? You're in the gang.
Oliver: But-but...
Dodger: The gang means family. We risked a lot to get you outta there.
Oliver: Look, I'm sorry, but all I ever wanted was—
Dodger: What-What? This place is not good enough for you anymore? Don't wanna mix with the Riff-Raff?
Oliver: No-No I like-I like everyone of you. But-but there was a little girl, and...I just wanna go back.
Rita: We never should've taken him, Dodge.
Oliver: Dodger, please!
Dodger: You wanna leave? Fine. There’s the door.
Einstein: But he just got here.
Dodger: Go on. No one’s stoppin' ya!
Tito: Hey, Dodger man, lighten up.
Dodger: You lighten up. If he doesn't like it, let him go.
(Dodger sulks in the recliner chair while Tito, Rita, Francis and Einstein look sadly at Oliver, before he sadly heads for the door)- The latter itself is pretty downbeat. Having nearly met the end of Sykes' deadline, Fagin just staggers in audibly sobbing, grabbing and latching onto his nearest lackey for comfort. Compared to Dodger, when he notices his collar, Fagin only seems wistful that one of his gang managed to find someone in the high life that would take them in (until he gets his plan at least).
- When the ransom meeting is planned through, and Fagin is confronted by Jenny, an emotional, frightened child with clearly not enough money to meet Fagin's now life-endangering debts. Fagin, clearly guilt-ridden by the situation, is now stuck in a Morton's Fork and after gazing at Oliver, who looks as defeated as him, he decides to pretty much sign his own death sentence and give the girl back her kitty.
- When Oliver realizes that Jenny has been kidnapped, he's visibly disappointed. The way he says "He took Jenny." is particularly gut-wrenching.
- After Sykes' demise, Dodger emerges with a seemingly lifeless Oliver. Believing him to be no longer alive, Jenny takes him into her arms and quietly cradles him. Her expression and the music that plays during the scene are downright heartbreaking. Even Dodger looks on the verge of tears.
- Roscoe and DeSoto are electrocuted in their last battle with Dodger, the former onscreen. Despicable as they were, it's a horrible way to go. Their whimpers as they pass on certainly don't help, even Dodger and Oliver show nothing but pity for them.
- If you've recently lost a pet, don't listen to "Good Company."
