Jon Hamm and wife Anna Osceola are preparing for their biggest role yet: parenthood! Multiple outlets reported on Monday, August 10, that Osceola, 38, is pregnant with her and Hamm’s first baby. Related: Jon Hamm and Wife Anna Osceola’s Relationship Timeline Amid Pregnancy News Not only did Jon Hamm win an Emmy for his role as Don Draper on Mad Men, but the show introduced him to his wife, Anna Osceola. Related: Jon Hamm Talks ‘Exciting’ Newlywed Bliss With Wife Anna Osceola John Nacion/Getty Images for Paramount Pictures Jon Hamm is loving his new role of husband to wife Anna Osceola. “We did it [where they had shot the Mad Men finale], which was also amazing.”