Kiernan Shipka Says It Was 'Intimidating' Acting Opposite Mad Men TV Mom January Jones
Kiernan Shipka and January Jones played Draper family members Sally and Betty, respectively, on seven seasons of Mad Men
Tom Cruise Returns to the Skies to Teach Fresh Navy Recruits in New Top Gun: Maverick Trailer
Top Gun: Maverick hits theaters May 27
Jon Hamm and Girlfriend Anna Osceola Make Red Carpet Debut at Oscars Viewing Party
The couple is believed to have met in 2015 when Osceola appeared on the final episode of Mad Men
Jon Hamm and Anna Osceola Enjoy Fun Day of Swimming and Snorkeling While Vacationing in Italy
Anna Osceola appeared alongside Jon Hamm on the final episode of Mad Men in 2015
Jon Hamm Reveals He and Harry Hamlin Once Auditioned to Play TV Dad Sandy Cohen on The O.C.
The Mad Men actor explained that he was often typecast for older roles in auditions because of his mature lookÂ
Jon Hamm and Anna Osceola Enjoy a Beach Day in Santa Barbara
Jon Hamm and Anna Osceola were first spotted together in 2017