Sexy: Anna Osceola Sexy Scenes, Pics & Videos

Born and raised in Cambridge, Massachusetts, Anna left the east coast for California once she decided she wanted to be an actress and hasn’t looked back since. She landed her first professional screen gig in 2007 when she appeared in the comedy series Not Another High School Show and then returned to television several times on shows like Saving Grace (2008), Greek (2008-2009), Rizzoli & Isles (2011), and NCIS (2012). In 2015, Anna can be seen in the series finale of the hit AMC show Mad Men, playing the receptionist at the spiritual retreat in California where the main character, Don Draper (played by Jon Hamm). That same year, Jon split from his partner of eighteen years, Jennifer Westfeldt, and then five years later, Anna and the much older Jon swere first romantically linked. They made it official in 2022 when they were both in the crime mystery flick Confess, Fletch and then the two were wed in 2023. Anna was also there in 2025 when Jon starred in the Apple TV+ series Your Friends & Neighbors. We got out first good look at the heavenly Mrs. Hamm when she donned a sexy swimsuit in the second episode. That captivating cleavage would drive any man mad!