10 'Emotional' Video Game Endings That Fell Completely FLAT
8. Yakuza: Like A Dragon

The above pic shows Ryo Aoki, one of the most eminently punchable scumbags in a series famed for its scumbag-punching.
Like A Dragon is no stranger to loathsome villains, and Ryo is one of the series' most reprehensible reprobates. A charismatic politician who campaigns on a platform of cleaning up Japan, Ryo is a ruthless monster who delights in tormenting the downtrodden. He deports illegal citizens after they sign up for a scheme promising them legal employment; he dismantles government programs designed to help the poor because of a grudge against the politician who founded them; and he taunts the aforesaid politician on the latter's deathbed.
Ryo is an amoral, sociopathic scumbag who thoroughly deserves the ass-kicking he receives at the end of the game. Which makes it all the weirder than Like A Dragon tries to generate sympathy for him at the end.
As it turns out, Ryo is actually protagonist Ichiban Kasuga's long-lost half-brother (because the Yakuza series is essentially a long-running soap opera, except every story arc ends with shirtless men beating seven bells out of each other). As Ryo lies dying in Ichiban's arms - having been stabbed by one of the many people he betrayed in his rise to power - Ichiban's tears feel wasted on the man he's grieving for.
Sorry for your loss, Ichiban, but after watching your brother be an irredeemable monster for 60 hours it's damn near impossible to join you in your tears.