- This article is about the boss monster. For the character, see Richard Grady.
When Travis first encounters his father, he has a flashback that manifests in the room he currently stands in. His younger self finds Richard hanging from a noose, who tells him he "won the game", and asks if he'd like the quarter that he still holds. Upon being told to wake up, Richard replies that he was never asleep and Travis knew this. He tells his son that remaining with him for so long was unhealthy. At this point, Travis snaps out of his flashback and tells his father "this is insane". Richard tells him it is time for him to face up to his responsibility and that he and Travis's mother will see him in Heaven. He then transforms into a gruesome monster.
The tan creature is composed of three main parts: one being in the middle, which is a distorted, huge mass that ends in a humanoid face, the only conceivable features being a nose (slightly) and a large mouth, which is full of human-like teeth and a very large tongue, its swollen size comparable with that of a corpse. On either side of the convulsing beast is a hollowed-out partial corpse, each being of the lower body. Sad Daddy hangs from the ceiling as if it is dropping down from the ceiling into a chained cage.
The creature itself doesn't move from its spot, but it can use its hanging tentacles to attempt to choke Travis, which may refer to Richard's method of suicide. It is able to vomit a stream of blood as well as bite Travis. The fight takes place in close quarters, which is the smallest area to fight a boss within the game. It is advised to use firearms such as the rifle or shotgun against this monster.
The creature is a manifestation of Richard Grady's memory and the guilt Travis suffers for feeling responsible for his death.
- The song that plays during the boss battle is an unnamed theme. The officially released song, "Monster Daddy", is different from the original theme.
- There is a state of confusion as to Richard's actual transformation. His head appears to become the base of the monster while his feet appear to become the head.
- It has two different death sequences: in the PSP version, its head thrashes around violently, spewing blood, then smashes into the ground and dies; in the PS2 version, it raises its head, emitting a sharp howl, and then falls down dead.