Every actor starts somewhere, and in this case a barely 5-year-old Macaulay Culkin made his debut as "Halloween Kid" in this 1985 TV movie that aired on ABC.
Culkin shared the screen with Hollywood legend Burt Lancaster and luminaries including Patricia Clarkson and Bill Pullman in the 1988 drama, about a dysfunctional family reunited for their patriarch's birthday.
This family drama with an A-plus pedigree (directed by Alan Pakula and starring Jeff Bridges and Farrah Fawcett, as well as Culkin's fellow child stars Drew Barrymore and Lukas Haas) came out in April 1989.
More memorable from the summer of 1989, however, was his turn as inquisitive nephew Miles in the John Hughes-written-and-directed Uncle Buck, starring John Candy—whose daughter Jennifer Candy, sweetly, met Culkin on the set of this film and they remain friends, decades later.
"I was just there, bowling," she recalled hanging out with the cast during the Uncle Buck bowling scene when she was a guest on Culkin's Bunny Ears podcast (recorded in his living room) in 2019. He agreed, "I very much looked forward to that, too. Like yeah, 'Oh, there's going to be a bowling sequence! This is great!' Yeah, you don't look forward to the washing-the-dishes scene."
As he noted himself while ranking his own films for his Bunny Ears website, Culkin couldn't really count this 1990 horror drama about a Vietnam vet played by Tim Robbins who's plagued by terrifying visions upon his return home among his favorites.
"I was not even in the credits," he noted of his minuscule role as Jacob's son Gabe, who's killed in an accident before his dad goes off to war. "And I was hit by a car."
Fun fact: Jacob's Thriller opened in theaters just two weeks before Home Alone.
It's up to Kevin McCallister to defend his home from a couple of (luckily idiotic and unarmed) burglars when his family accidentally leaves the country without him for Christmas vacation in the 1990 blockbuster. Made for only $18 million, Santa left $477 million under the box office tree and Culkin became a 10-year-old superstar.
That's Culkin rocking out at the beginning of Michael Jackson's cinematic music video for "Black or White," the first single off of the artist's 1991 album Dangerous.
Culkin's friendship with Jackson began when the singer, recognizing a kid who was about to have the weight of the fame world on his shoulders, reached out after Home Alone became a global phenomenon—and their bond endured until Jackson's death at 50 in 2009.
"I talked to him like he was a normal human being...He's just a guy, who's very kid-like himself," Culkin, who is a close friend and godfather to Michael's daughter Paris Jackson, said on Larry King Live in 2004. The following year he testified that Jackson was never inappropriate with him when the Grammy winner was on trial for—and was acquitted of—charges of child molestation.
One day we'll probably get over (kidding, we'll never get over it) the demise of Thomas J. from bee stings in this coming-of-age dramedy from 1991.
If only Anna Chlumsky's Amy from Veep could go back in time and tell those bees to get the f--king f--k away from her best friend!
He reprised the role of Kevin—and his famous scream—for the 1992 sequel that found the rambunctious grade-schooler managing to make it to the airport with his family but, after mistaking another coat-wearing traveler for his dad, ending up on a flight to the Big Apple instead of to Florida with the rest of the McCallisters.
The movie was a raging success, making $365 million worldwide.
Elijah Wood's Mark senses there's something off about his cousin Henry in this R-rated Omen-esque thriller from 1993, co-starring Culkin in the bad seed role—which at the time was considered a risky career move. (Minus the countless think pieces that have since diagnosed Kevin McCallister as a psychopath.)
So many productions based on the classic Balanchine ballet, so little time, but in this one from 1993 Culkin was Drosselmeier's Nephew, as well as the titular toy come to life.
Part-live action, part-animated, Culkin played a shy boy who finds his inner hero after he's sucked into the pages of an adventure tale when he pops into a library to take refuge from a storm in this 1994 fantasy.
Because in movies no grownup is savvy enough to avoid being pranked by a 13-year-old, Culkin's Timmy easily gets his criminal dad, played by Ted Danson, to take him along for what turns out to be a wild ride of father-son bonding and a little thievery in this 1994 comedy.
Unbeknownst to his fans, Culkin's turn as the richest boy in the world (but the moral of the story is that money doesn't matter if you don't have friends to invite to your personal McDonald's), which came out Dec. 21, 1994, would be his last movie for almost a decade.
"It was the last movie I made for 20 years," the former child star told Bunny Ears, exaggerating just a bit. "John Larroquette [who played villain Laurence Van Dough] hated me, but we bonded over Barq's root beer because he was from Louisiana and that's where Barq's was made. Also, everyone in the cast was over 6-foot-2 in order to make me look shorter and younger than I was at the time."
Based on real-life events, Culkin played "King of the Club Kids" Michael Alig, who spent almost 17 years in prison for manslaughter after he and Robert "Freeze" Riggs killed and dismembered fellow New York nightlife aficionado Andre "Angel" Melendez in 1996. Riggs also served prison time for manslaughter.
To prepare for the role, Culkin visited Alig behind bars, telling Barbara Walters in 2003, "We spent four hours at the prison. I'd never been to prison before. I kind of just was listening and I was watching how his hands moved...He seemed remorseful, but at the same time he was putting up this facade. He was putting on the 'Michael Alig' act for me, the wild and crazy guy."
Asked if he, too, had a dark side, the then-25-year-old actor said, "I guess you can say that. But not anywhere near as dark as him. It's so easy to see me as this wicked, little thing, you know? This wicked little, like, you know, blond-haired kid, making trouble for everybody."
Moreover, he recalled to Bunny Ears of the glam-rock look that was essential to Michael, "I always felt pretty, but that's where I learned I actually was pretty. It taught me to totally understand why women put in all that time getting ready. It's worth it and I looked awesome."
Acknowledging his long break from the limelight, Culkin, who was appearing in his first movie since Ri¢hie Ri¢h, told Walters, "I don't want to do what I did before. Before it was, you know, it was like people's livelihoods were on the line...They like built an industry out of me. It was just this really odd dynamic that I think made me uncomfortable for a lot of my young life. I'm not one of those people who needs that gratification of doing like 10 films a year...I'm just trying to be, you know, an artist."
The 2004 satire, in which he played the non-religious brother of Mandy Moore's fervent evangelical Christian, ranks up there among Culkin's favorites because, as he told Bunny Ears, "Mandy Moore is a delight. I also got to be in a movie with people who were all my own age for once. All the other movies had been me as a kid with adults. On Saved! I was the only one who was old enough to buy liquor."
Culkin practiced using a wheelchair for several months before filming began and studiously observed people who use chairs to make his movements as authentic as possible.
The indie comedy from 2007 further proves that having anonymous sex with others, even followed by breakfast—as prescribed by Culkin's therapist character James—isn't the best way to fix the troubled relationship you're currently in.
"I read a lot of material and loved this script," Culkin told Variety about what drew him to the film. "It's really about the pressure that leads them to experiment, the anticipation leading up to the event and then the fallout."
This 2009 drama, a modern-day retelling of the biblical story of King David, starred Ian McShane and Sebastian Stan and only lasted for one season, but featured Culkin as the king's nephew Andrew, returned from exile. (And, because it's a small world after all, brother Kieran Culkin's future Succession dad Brian Cox was in it too, playing the former king of another territory.)
Culkin had a running cameo as a New York barista version of himself in the TV Land comedy.
"We were trying to establish an ongoing disagreement me and Adam Goldberg's character had about what a barista looked like," Jim Gaffigan explained to TV Insider about how Culkin's involvement in the show came about. "And so, the idea of the barista being someone famous or kind of legendary is just like an ongoing thing. Like you know in everyday life, someone will be like, 'Yeah, you know that waitress that looks like Julia Roberts?' You know what I mean?"
He continued, "I had met Macaulay when I reoccurred on That '70s Show and he was dating Mila [Kunis], but a comedy club manager also grew up with him. And so, I just kind of broached the idea and through him reached out to Macaulay. And he was into it. We kind of brought it up where, 'Wouldn't it be funny if he came back and did this?' So we just kept trying to figure out different ways where Macaulay just kind of comes up in Jim's life as a joke, but also reflecting what happens in everyone's life where you go, 'I keep seeing that guy.'"
Culkin joined Breckin Meyer and Seth Green in this 2019 ensemble dramedy about estranged pals reuniting and confronting life's challenges and mundanities on a trip to Thailand.
It's become apparent through his fascinating choice of guest appearances over the last couple decades that Culkin relishes randomly popping up in projects, and so he did in one 2019 episode of this Hulu series, starring Kat Dennings as web designer Jules, who after putting all of her girlfriends on the back burner while she focused on her boyfriend is trying to reconnect with her pals after getting dumped.
Culkin played Dan, a guy Shay Mitchell's Stella met while on vacation who strikes Brenda Song's Madison as a possible serial-killer type.
Though in real life, Culkin struck Song as long-term partner material.
Delayed almost a year by the real-life horrors of the COVID-19 pandemic, Double Feature eventually premiered in August 2021, featuring Culkin's debut in the anthology series as Mickey, a hustler who dreams of making it as a screenwriter but ends up in the pill-peddling business. Only the pills turn talented people like him into pale, blood-sucking creatures. And we don't mean Hollywood agents.
The best Culkin cameo remains a surprise cameo, and so it was when he popped up on a pair of February 2022 episodes of the HBO comedy, playing Harmon, the now-grown son whom Walton Goggins' Baby Billy Freeman abandoned in a shopping mall as a kid and visits to make amends. Better yet, Baby Billy lets Harmon take a swing at him to soothe his wounded feelings.