Jon Hamm's Pregnant Wife Anna Osceola Debuts Baby Bump at Emmys 2026

Why Emmys 2026 Is on Monday, Not SundayJon Hamm is getting a new role: Dad. The Mad Man actor’s wife Anna Osceola debuted her baby bump at the 2026 Emmy Awards Sept. 14 as the couple walked the red carpet at the Peacock Theatre in Los Angeles. Hamm and Osceola highlighted their happy milestone with the Law & Order actress gently cradling her bump while donning a black and white gown. Hamm, of course, kept it classic in a black tuxedo. And Hamm has been teasing his plans to grow his family with Osceola since the couple tied the knot in June 2023. “I hope it turns into kids,” the 55-year-old told The Hollywood Reporter in 2024. “I will be the old dad, but so it goes. It could be a good thing. We’ll see.” Indeed, Hamm noted that taking the next step with the 38-year-old—whom he met on the set of Mad Men in 2015—felt terrifying, but worth it. “I didn’t look at marriage as a thing,” Hamm continued. “Obviously, my parents were not married long, so I don’t have a model to look at and go, ‘Oh, this is how one finds happiness.’ I just knew at a certain point I wanted to be with this person.” As Hamm explained, “When I proposed, I was terrified. I was like, ‘What am I doing?’” But it was because of that feeling that Hamm knew it was right for him. As he put it, “I just remember feeling, ‘This is really scary,’ Then going, ‘Well, it probably means it’s worthwhile.’” Randy Shropshire/NBC via Getty ImagesFor Hamm—who dated Jennifer Westfeldt for nearly 20 years before their 2015 breakup—meeting Osceola marked a shift in his priorities for his personal life. "It's only been in the last couple of years, me kind of sitting down and really thinking about all that stuff that's made the relationship that I'm in now even more meaningful," Hamm explained during an appearance on The Howard Stern Show in 2022, “and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness—all that stuff.” While the Bridesmaids alum admitted that it sounded “hokey” he emphasized that his desire for those things was very “real.” “It’s what I’m working for,” he continued. “What else is there other than that?” For more stars on the red carpet, keep reading. Photo by John Shearer/WireImageNicole Brydon BloomJohn Shearer/WireImageEunice BaeJesse Grant/NBC via Getty ImagesDesi LydicKevin Mazur/Getty ImagesDenée BentonPhoto by Kevin Mazur/Getty ImagesChris PerfettiPhoto by LISA O'CONNOR / AFP via Getty ImagesLinda Cardelliniin Yara Shoemaker. Photo by Kevin Mazur/Getty ImagesKarolina Wydrain Marmar Halim. Photo by Monica Schipper/Getty ImagesShailene Woodleyin Balenciaga. Jesse Grant/NBC via Getty ImagesNicole Kidmanin Chanel. Kevin Mazur/Getty ImagesCharles MeltonJesse Grant/NBC via Getty ImagesSarah Pidgeonin Chanel. Monica Schipper/Getty ImagesZendayain custom Prada. Amy Sussman/Getty ImagesBrenda Song & Macaulay Culkinin Oscar de la Renta (Song). Photo by LISA O'CONNOR / AFP via Getty ImagesConstance Zimmerin Akris and Kwiat jewelry. Monica Schipper/Getty ImagesCharlie HunnamPhoto by: Randy Shropshire/NBC via Getty ImagesCarey Mulliganin The Row. Randy Shropshire/NBCIsa BrionesRandy Shropshire/NBCLaw Roachin Givenchy. Randy Shropshire/NBC via Getty ImagesJulianne Houghin Antonio Grimaldi. Randy Shropshire/NBCSepideh MoafiRandy Shropshire/NBCQuinta Brunsonin Christian Cowan, Jimmy Choo shoes and Marco Bicego jewelry. Randy Shropshire/NBCAlan CummingKevin Mazur/Getty ImagesOdessa A'Zionin Jean Paul Gaultier. Monica Schipper/Getty ImagesHannah EinbinderMonica Schipper/Getty ImagesChase Infinitiin Louis Vuitton. Monica Schipper/Getty ImagesJean SmartAmy Sussman/Getty ImagesEmmy Rossumin Julie de Libran. Kevin Mazur/Getty ImagesDakota Fanningin Carolina Herrera. Monica Schipper/Getty ImagesElle FanningMonica Schipper/Getty ImagesKate O'Flynn