Coincidentally, Anna Osceola joined Jon Hamm when he took his final "Mad Men" bow in the series finale — Season 7, Episode 14, "Person to Person." After being brought on a journey to a remote wellness retreat, Don Draper hits rock bottom and admits many of his faults to Peggy Olson (Elisabeth Moss) before leaving his life behind for good. That is until a meditation session inspires him to create one of the greatest Coca-Cola ads — and one of the greatest ads, period — of all time.
Osceola plays Clementine, a young woman who works at the retreat. When his original companion, Stephanie (Stephanie Drake), leaves after having a breakthrough in a group therapy session, Don finds himself stranded with no way of getting home. Clementine encourages him to finish his stay, admitting that his chances of getting a car within the next few days are slim to none. Not only does their chat successfully convince him to stay a while longer — she seemingly inspires a red-clad, pigtailed woman that ultimately appears in the Coke ad. Since appearing on "Mad Men," Osceola has guest-starred in episodes of "Law and Order: SVU" and "Bull."
