Culkin has the unique distinction of being an ex-child star who, instead of diving headfirst into a pile of self-loathing and self-destruction when his star faded, has instead turned himself into a very lovable cult figure.
In case you haven't been following him, this is a man who spends his spare time showing up to underground wrestling matches and throwing balls into the ring, Kevin McCallister-style. This is a man who spent three years in a Velvet Underground cover band that re-wrote all those classic Lou Reed lyrics so they'd be about pizza.
Pizza Underground made it clear that Culkin was basically just hanging out with un-famous people in Los Angeles, behaving like an art school student who definitely hadn't made $20 million before the age of 14.
For years now, Culkin has been living his best Warholian life. In 2012, he turned his $2 million New York loft into an artists' workshop and invited two members of The Moldy Peaches to live with him. When a reporter and photographer from Bullett magazine went over to see what was going on, Culkin and his roommates showed them around, while all dressed up as Kurt Cobain.
Since starting a lifestyle parody website and podcast named Bunny Ears last year, articles from the site have included: "Exclusive: Macaulay Culkin Interviews the Swarm of Bees From 'My Girl'" and, in reference to that famous scene from Mrs. Doubtfire: "The Best Cakes to Smash Into Your Face When Trying to Fool a Social Worker."
Culkin's YouTube channel is even more ridiculous, featuring (among other things) video after video of him telling you he's going to teach you how to beat a variety of retro games (like Simon, Rubik's Cube and Battleship), while never actually teaching you how to beat retro games. He probably doesn't ever succeed at his end goal because of the copious amounts of white wine he drinks throughout.
Ultimately, Culkin has figured out ways to be artistically fulfilled without following the Hollywood path that made him famous. He cares about art, and music, and making you laugh, and—most importantly—he doesn't care about making fun of himself, or looking silly in the process. What's more, Culkin has taken ownership of all the things the public found so annoying when he was at the peak of his fame in the '90s, and embraced them in a way that screams self-acceptance.
With all that considered, it's no wonder he's friends with Lizzo.