- 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 hem 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!
- To add a little to it for history's sake, the Twin Towers of the World Trade Center feature quite evidently on the introductory tune, considering their Real Life fate on 9/11. STAB! RIGHT IN DA FEELS.
- 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.
- When Oliver realizes that Jenny has been kidnapped, he's visibly distraught. The way he says "He took Jenny!" stabs you in the feels.
- 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.
- 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).
- After Syke's death, Dodger emerges with a seemingly lifeless Oliver. Believing him to be dead, Jenny takes him into her arms and silently cradles him. Her expression and the music that plays during the scene are downright heartbreaking. Even Dodger looks on the verge of tears.
- Admit it, you felt a pang of sympathy for Roscoe and De Soto after seeing them electrocuted onscreen in their final battle with Dodger. Despicable as they were, it's a horrible way to go. Their whimpers as they die certainly don't help.
Tear Jerker / Oliver & Company