Oscars 2025: Conan O’Brien Gives Ryan Reynolds’ Deadpool Shoutout

And it has already proven to be a night to remember. Indeed, shortly after Conan’s musical number, Kieran Culkin brought home the first award of the evening for Best Supporting Actor in A Real Pain. For his first ever nomination and win, The Succession alum beat out The Apprentice’s Jeremy Strong, The Brutalist’s Guy Pearce, Anora’s Yuriy Borisov, and A Complete Unknown’s Edward Norton. (See every winner so far here). 

Naturally, Kieran used the opportunity to poke fun at his wife Jazz Charton—with whom he shares two kids. 

“I love you Jazz,” he gushed. “About a year ago I was on a stage like this and I very stupidly publicly said that I want a third kid from her because she said if I won the award, she would give me the kid. Turns out she said that because she didn’t think I was going to win.”

The camera then cut to Jazz, who shrugged in agreement while smiling as her husband delivered his speech.  

And Kieran admitted that he told his wife after accepting his Emmy that he really wanted four kids. To which the new Oscar winner cheekily recalled she replied, “‘I will give you four when you win an Oscar.’”

The crowd erupted in cheers as Kieran finished his speech. 

“I held my hand out, she shook it, and I haven’t brought it up until just now,” he added. “You remember that honey? You do?”

He finished, as his wife shook her head, “Let’s get cracking on those kids.”

Keep reading to see more winners at the 2025 Oscars….