Kieran Culkin Hijacks Jon Hamm’s ‘SNL’ Monologue in Hilarious Cameo – Oscar Shade, Showdowns, and Pure Chaos

Jon Hamm kicked off his return to Saturday Night Live with the kind of monologue only Jon Hamm could pull off — full of self-deprecating charm, dry wit, and unexpected digs at himself. What started as a reflection on the art of the cameo quickly turned into a comedic showdown when Kieran Culkin unexpectedly walked on stage mid-monologue.

“I know a cameo may seem inconsequential,” Hamm joked, “but it really is an important part of the show.” Just as he leaned into his speech about elevating sketches, Culkin strolled in with perfect timing. The moment immediately shifted into a back-and-forth full of jabs, mock egos, and perfectly timed insults.

“This is my monologue,” Hamm told Culkin, trying to reclaim his spotlight.

“I know, I’m just making a cameo,” Culkin shrugged, delivering the line with a smirk that only made it funnier.

What followed was pure comedic gold. Hamm, embracing his inflated persona, demanded Culkin hand over his Oscar. Culkin refused, of course, leading to a spirited (and completely unserious) debate about whose TV legacy reigns supreme: Mad Men or Succession.

The crowd loved it — two powerhouse actors pretending to be petty on live television, each throwing light-hearted shade at the other while keeping the audience in stitches.

It wasn’t just about the jokes, though. The moment highlighted the cultural clash of two iconic TV eras. Mad Men defined prestige drama in the early 2010s, while Succession took over the cultural conversation in recent years. Seeing their stars go head-to-head, even in jest, felt like the perfect encapsulation of how TV has evolved — and how its biggest names still don’t take themselves too seriously.

Culkin, who’s currently in New York for his Broadway role in Death of a Salesman, slid into the cameo like a pro, while Hamm showed he still knows how to command the SNL stage — with or without an Oscar in hand.