Kieran Culkin, 42, clinched the 2025 Best Supporting Actor Oscar for “A Real Pain” on March 2, capping a dominant awards run after Golden Globes and SAG victories.

Yet, his speech stole the spotlight, playfully nudging wife Jazz Charton for a fourth child. The win over Guy Pearce, Yuriy Borisov, Edward Norton, and Jeremy Strong marks his leap from “Succession” Emmy champ to movie star.

Culkin thanked director Jesse Eisenberg, calling him a genius—though not to his face. Then, he recounted a year-ago Emmy plea for a third kid, joking Charton agreed, thinking he’d lose. Post-Oscar, she upped the ante in a parking lot chat, promising four if he won an Oscar. With the statuette in hand, he teased her live: “Let’s get cracking on those kids.”

From Bet to Baby?

The couple, parents to two, now face their pact’s payoff. Culkin’s quip—“No pressure, I love you”—drew laughs, but fans wonder if it’s serious. After recalling her “I owe you a third” line, he’d pushed for four, and her Oscar wager sealed it. Transitioning from jest to reality, his win might mean a bigger family soon.

Career Peak Meets Family Fun

Culkin’s “A Real Pain” role cemented his rise, outshining a tough field. Now, his Oscar night doubles as a personal milestone. Will Charton greenlight babies three and four? For now, his cheeky plea keeps the crowd—and headlines—buzzing.


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