Macaulay Culkin shot to fame as the sassy Kevin McCallister in iconic 1990 film Home Alone, carving out his reputation as the number-one child star in the world.

His hilarious role in the wholesome family comedy and its 1992 sequel saw him win the adoration of millions with his sweet bond with his mother and determination to defend his family home from thieves.

But in 1993, the star — then at the height of his fame — shocked fans with an incredibly dark new role, as he played a psychopathic, murderous child in the thriller The Good Son.

Fans of the kindhearted Kevin were left reeling as babyfaced Culkin — then 12 — dropped the F-bomb, tortured his cousin (played by future star Elijah Wood) and killed off his sibling — before attempting to murder his mother by pushing her off a cliff.

The Good Son follows 12-year-old Mark, who is sent to stay with his aunt (Wendy Crewson) and uncle (David Morse) in Maine following the death of his mother and while his father is away on business in Tokyo.

Macaulay Culkin shocked fans when he played a murderous child in the 1993 thriller The Good Son

Macaulay shot to fame as the sassy Kevin McCallister in the iconic 1990 film Home Alone, carving out his reputation as the number-one child star in the world

He is introduced to his 12-year-old cousin Henry (Culkin) who at first brands him a ‘brother’ before his twisted behavior begins to exhibit itself.

The pair experiment with a crossbow, which Henry uses to shoot a dog that barked at him.

Henry then builds a dummy called ‘Mr. Highway,’ whom he then throws off a bridge and onto a busy highway — causing a huge vehicle pile-up — as a terrified Mark screams, despite Henry’s threats.

Henry’s attention then turns to his eight-year-old little sister Connie (played by Macaulay’s real life sister Quinn), whom he pushes toward thin ice while the pair ice skate, causing her to fall into a coma.

Mark tries to tell Henry’s mom, who then finds Henry trying to suffocate Connie in her hospital bed.

She finds a rubber duck Henry had hidden in the shed, which once belonged to his late younger brother Richard, who drowned in the bathtub.

Henry vows to kill Susan due to his jealousy over Mark and her relationship, with a memorable scene showing Mark telling Henry: ‘She’s my mother now.’

Henry responds: ‘Hey Mark, don’t f*** with me.’

Fans of the kindhearted Kevin were left reeling as babyfaced Culkin — then 12 — dropped the F-bomb, tortured his cousin (played by future star Elijah Wood) and killed off his sibling, before attempting to murder his mother by pushing her off a cliff

Wood plays Mark, who is sent to live with his aunt and uncle in Maine following the death of his mother. He is introduced to his 12-year-old cousin Henry (Culkin), who at first brands him a ‘brother’ before his twisted behavior begins to exhibit itself

The pair experiment with a crossbow, which Henry uses to shoot a dog that barked at him

Henry heads out on a walk with Susan with plans to murder her.

Susan confronts Henry, asking him if he killed Richard, to which Henry replies: ‘What if I did?’

Following a chase Henry pushes Susan off a cliff but Mark saves her life by tackling the murderous pre-teen.

Susan manages to climb back up just in time to grab hold of the boys as they roll over the edge, one in each hand.

With only enough strength to save one child, Susan lets go of Henry, with the child falling to his death.

The film made $60.6 million worldwide against a budget of $17 million but was widely panned by critics.

Wood — then 12 — would become a huge worldwide star just eight years later with his starring role as Frodo Baggins in the Lord Of The Rings trilogy.

Culkin — now 43 — retired from acting shortly afterwards but he is set to join his four brothers  in the upcoming Prime Video animated series The Second Best Hospital In The Galaxy.

Henry then builds a dummy called ‘Mr. Highway,’ whom he throws off a bridge and onto a busy highway — causing a huge vehicle pile-up — as a terrified Mark screams, despite Henry’s threats

Henry vows to kill his mother Susan due to jealousy over Mark and her relationship, with a memorable scene showing Mark telling Henry: ‘She’s my mother now.’ Henry responds: ‘Hey Mark, don’t f*** with me’

Susan confronts Henry, asking him if he killed Richard, to which Henry replies: ‘What if I did?’ Following a chase Henry pushes Susan off a cliff but Mark saves her life by tacking the murderous pre-teen

The pair fight as Henry attempts to kill once again

Susan manages to climb back up just in time to grab hold of the boys as they roll over the edge, one in each hand. With only enough strength to save one child, Susan lets go of Henry, with the child falling to his death

The thrilling casting call features Macaulay, Kieran, Rory, Christian and Shane Culkin, all of whom began their acting careers in childhood and are now in their 30s and 40s.

Kieran voices one of the main characters, Dr. Plowp, with Plowp’s siblings being voiced by the Succession star’s real-life brothers.

The roster of Culkin siblings also includes sisters Quinn Culkin, Dakota Culkin — who died after being struck by a car in 2008 — and half-sister Jennifer Adamson, who died of an overdose in 2000.

The Second Best Hospital In The Galaxy showrunner Cirocco Dunlap revealed on Tuesday that Keiran was the one to suggest the Culkin clan star together in the series.

‘So Kieran came up for the role of Dr. Plowp and in a crazy turn of events, the bird alien [character that he plays] had four brothers [in the script] before he was cast,’ Dunlap told The Hollywood Reporter.

‘So he had the four brothers already and when we cast Kieran we were like, “You have four brothers! That’s ridiculous, what fate,”‘ Dunlap continued.

‘Kieran was the one who suggested it, he was like, “We could get my brothers” and I was like, “What? Yes, yes we should.” And they’re so wonderful, they’re so funny, they’re very empathic and very sweet.’

However, it turns out Natasha Lyonne, who plays Nurse Tup in the show, was the one to seal the deal.

Culkin — now 43 — retired from acting shortly afterward, but he is set to join his four brothers in the upcoming Prime Video animated series The Second Best Hospital In The Galaxy (pictured December 2023)

The thrilling casting call features Macaulay, Kieran, Rory, Christian and Shane Culkin, all of whom began their acting careers in childhood and are now in their 30s and 40s; Rory and Keiran on the set of 2008’s Lymelife

Kieran voices one of the main characters, Dr. Plowp, with Plowp’s siblings being voiced by the Succession star’s real-life brothers; still from The Second Best Hospital In The Galaxy

Episode six of The Second Best Hospital In The Galaxy will see Kieran’s character joined by his cosmic siblings; Christian and brother Kieran Culkin attend the The Starry Messenger cast party on November 16, 2009

Drama has surrounded the Culkin family since Macaulay rose to fame in the 1990s through his roles in Home Alone and Uncle Buck

‘The magic of Natasha, she made a call — I think she picked up the Culkin Batphone and they all answered,’ quipped Maya Rudolph, who is lined up to lend her voice to Dr. Vlam.

Natasha chimed in at the time, ‘I’m the Culkin whisperer it turns out.’

‘I worked with Mac on Party Monster, I want to say it was five years ago but it was probably 25.

And so we became pals, we were instant friends and he’d do running charades and the family would all be there.

Kieran and I became pals along the way, I think maybe I did a movie with Rory.

‘I love them, I really love those Culkins,’ she added.