By Amber Humphrey

Macaulay Culkin was arguably the most successful child actor of all time. At the height of his career in the ’90s, he was making $8 million per film. While most of us would be pleased with bringing home that kind of cash for as long as people were willing to fork it over, Culkin decided to take a ten-year sabbatical from acting after 1994’s Richie Rich. The path Culkin’s life has taken since that break seems to be based more on whim than on any kind of professional drive. Culkin is a free spirit, and he recently told Vulture that he spends his days “whatevering.” Thankfully, that “whatevering” is usually pretty offbeat and weirdly incredible.

Party Monster (2003)

This movie about the drug-addled club kids of the ’80s and ’90s kicked off Culkin’s second act — it was his grown-up debut. Mac was back, but this time around he was taking on more complex roles and was down to wear a little glitter lip gloss if the need arose.

Saved (2004)

As a kid, Culkin received top-billing in pretty much everything he’d done. But he reemerged after his prolonged hiatus as a truly compelling character actor. Here, Culkin plays Roland — the sardonic heart of this witty teen movie about a devout Christian girl who ends up pregnant.

The Pizza Underground (2013)

Culkin and some pals formed what just might be the most important pizza-themed band ever: The Pizza Underground. The group plays Velvet Underground covers but they change the lyrics and song titles to reflect the aforementioned pizza theme. So, the Velvet Underground’s “All Tomorrow’s Parties” becomes “All the Pizza Parties.” “I’m Waiting for the Man” becomes “I’m Waiting for the Delivery Man.” If that weren’t twee and awesome enough, the band’s instrumentation includes a glockenspiel, a tambourine, and a pizza box (naturally). Culkin plays the kazoo.

More Pizza (2013)

One time, he ate a slice of pizza. (It’s actually an homage to an Andy Warhol video.)

The Jim Gaffigan Show (2015)

Proving that he’s transcended regular stardom and has moved to some kind of higher, infinitely more interesting, meta level of celebrity, Culkin showed up on comedian Jim Gaffigan’s TV Land sitcom as a barista who looks like Macaulay Culkin. The Culkin cameo raises two really important questions: Are Mac and Gaffigan real-life buddies, and how would one go about procuring an invite to one of their kick-back sessions?

Grown-Up Kevin McCallister (2015)

In a web series called DRYVRS, Culkin plays a manic, older version of Home Alone’s burglar-thwarting Kevin McCallister. Adult Kevin is emotionally scarred and has finally realized that his parents’ habit of leaving him home alone was actually pretty horrific.

DIY Live-Action Aladdin (2016)

This April, Culkin will star in his friend Adam Mack’s live-action reimagining of Aladdin. The day-glo sets for this insanely inventive and totally necessary DIY effort were made with materials like cardboard boxes and crayons. Culkin portrays a protestor who is decapitated. Regardless of how this movie ultimately turns out, the fact that Culkin remains so lighthearted and game for whatever — when so many child actors struggle post-fame — is delightfully cool.