MACAULAY Culkin recently made headlines when he popped the question to baby mom Brenda Song.
The former child star rose to fame starring in Home Alone, as well as its sequels, before immersing himself in controversy.
Here's a look at her transformation over the years:
WHERE'S KEVIN?
Macaulay rose to fame in 1990 when he played Kevin McCallister in Home Alone.
The blonde child star played a cheeky character who was abandoned by his family over the holidays and had to defend his home from two burglars.
His most iconic scene was when he used aftershave for the first time and was shocked by the bite.
He was just ten years old at the time.
BIG STAR
Following his success in Home Alone, Macaulay received movie roles left and right in 1991.
He starred in My Girl opposite Anna Chlumsky, Dan Aykroyd and Jamie Lee Curtis.
She was on screen for only half an hour and left quite an impression on viewers.
Macaulay had also become close friends with Michael Jackson and the two even collaborated on a music video.
After making 15 films in just seven years, she retired from acting in 1994 to lead a "normal life."
WEDDING BELLS?
Macaulay stayed under the radar until he revealed that he had married actress Rachel Miner.
The young couple were just 18 years old and their marriage lasted four years in total.
They separated in 2000 and finalized their divorce in 2002.
AGAIN
Macaulay came out of retirement in 2000 when he appeared in Madame Melville.
At the time, Macaulay was dealing with the deaths of two of his sisters: Jennifer, who died of an overdose, and Dakota, who died in a car accident.
After finalizing their divorce, Macaulay began dating actress Mila Kunis in 2002.
The couple were together until 2011 when they called it quits over something Mila allegedly did.
She told Dax Shephard on his podcast: "I screwed up, but everyone forgave everyone for what happened."
It was also around this time that the actor revealed that he slept with Michael Jackson, but fully defended the singer against allegations of child sexual abuse.
ARRESTED
Macaulay continued his downfall when he was arrested in 2004 for drug possession.
After pleading guilty, he received three one-year suspended prison sentences and was ordered to pay $540 in court fees.
However, his mugshot has been seen all over the world.
GIVING MUSIC A CHANCE
In 2013, Macaulay tried his hand at music and performed with The Pizza Underground from 2013 to 2018.
But success alluded to him, and he was booed by concertgoers who threw beer at the band during a 2014 show that made headlines in England.
CELEBRITY COUPLE
In 2017, the actor made another comeback when he began dating Disney Channel actress Brenda Song.
The two met while filming the movie Changeland and have been together ever since.
The two had their first child together in August 2021, a boy they named Dakota Song Culkin.
AMERICAN HORROR STORY
Macaulay made another return to the small screen when he appeared in the most recent season of American Horror Story.
His role as Mickey, a failed screenwriter who turns to prostitution, was praised by fans and critics alike.
Most recently, he was seen walking the runway for Gucci, also receiving much praise.
Macaulay Culkin is worlds away from Home Alone as he makes his American Horror Story: Double Feature debut in the Season 10 trailer
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