Anna Osceola's Mad Men Character Explained (She Wasn't A Don Draper Love Interest)

Summary Anna Osceola played a crucial role in the Mad Men series finale as counselor Clementine, impacting Don Draper's emotional breakthrough.

Osceola's character Clementine in Mad Men inspired Don Draper's creation of the iconic 1971 Coca-Cola ad, showcasing her importance in the series.

Despite being known as Jon Hamm's wife, Osceola continued her acting career post-Mad Men, starring in TV series like Law & Order.

Many know Anna Osceola as Jon Hamm's wife, and while the pair did meet on the Mad Men set, many are surprised to learn who Osceola played. The acclaimed AMC series centers around Hamm's Don Draper, an advertising executive in 1960s New York who's a chronic womanizer. Don is repeatedly unfaithful throughout both of his marriages, finding sexual conquests at the office, swanky Manhattan cocktail bars, and even California, a place near and dear to Don's heart that he visits frequently throughout the show.

It's California where Don finds himself in the series finale, and the Mad Men ending sees him the lowest he's ever been. He's all alone, having divorced Megan (Jessica Paré), and has recently learned that his other ex-wife, Betty (January Jones) has terminal lung cancer. Despite her prognosis, Betty doesn't want their children to live with Don. Full of regret, Don turns to the one woman left in his life, Peggy (Elisabeth Moss), but she's an entire coast away. However, Don also finds unexpected comfort in Anna Osceola's Mad Men character, who has a huge impact on the protagonist.

Related Mad Men Cast & Character Guide From Jon Hamm to Elisabeth Moss to John Slattery, the cast of Mad Men is full of widely praised actors, each playing a complex character.

Anna Osceola Plays Clementine In The Mad Men Series Finale

Clementine Is A Counselor At A California Retreat Where Don Is Staying

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Don goes to California in the Mad Men series finale, "Person to Person", and reunites with Stephanie Horton (Caity Lotz), who convinces him to go to a spiritual retreat with her. However, after a personal crisis, Stephanie flees the retreat, leaving Don stranded. It's here where Don meets Anna Osceola's Clementine. Clementine works as a counselor at the retreat, and though Don is desperate to leave, she encourages him to attend a group therapy session with her. In the therapy session, after witnessing another man break down in tears, Don has his own emotional breakthrough.

Had it not been for Clementine, Don likely would have left the retreat and never had the release he needed. But Clementine's importance to Mad Men doesn't end there. In the very last scene of the series, Don, still at the retreat, is in a meditation session when he gets the inspiration for the real-life 1971 Hilltop Coca-Cola commercial.

In addition to the 1971 Coca-Cola ad, Mad Men drew from real-life 1960s advertisements several times for their storylines.

In the ad, a diverse group of people sing "Buy the World a Coke" while holding glass bottles of the soda. One of these people is a young woman bears a striking resemblance to Clementine, complete with a similar white-and red dress and braided hair with red ribbons. The commercial is widely considered one of the greatest ads of all time, and Don never would have dreamt it up without Clementine.

What Osceola Has Been Up To Since Mad Men

Osceola Has Continued To Work In TV, Including Two Dick Wolf Shows

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Just like Don couldn't get Clementine out of his head, Anna Osceola clearly left an impression on Jon Hamm, as the two actors quietly dated after the show wrapped, and were married on June 24, 2024 (via People). And while Osceola may not be as big of a name as her husband, she has continued to work since her role on Mad Men. Osceola appeared in two Dick Wolf universe series, in Law & Order: SVU as Janie Spears and a four-episode stint on Law & Order True Crime as Noelle Terlesky. She also guest-starred on an episode of an episode of the legal drama Bull as Kira Petrova.

Anna Osceola's Post-Mad Men Roles Title Character Year # of Episodes Animal Control Tiffany 2024 1 Curb Your Enthusiasm Club Waiter 2024 1 Confess, Fletch Larry 2022 Movie Law & Order True Crime Noelle Terlesky 2017 4 Bull Kira Petrova 2017 1 Law & Order: Special Victims Unit Janie Spears 2016 1

After 2017, there's a five-year gap in Osceola's resume, but she returned to acting in 2022, playing Larry in the Jon Hamm-led caper comedy Confess, Fletch. Most recently, 2024 saw Osceola appear in two other TV series, Curb Your Enthusiasm's final season as a club waiter and Animal Control as Tiffany. Clementine may be Anna Osceola's most prominent role, but if her Mad Men appearance is anything to go by, she's an actress worth paying attention to.