10 Best 'Mad Men' Guest Stars, Ranked
Mad Men is the award-winning TV series that follows the enigmatic Don Draper (Jon Hamm) as he takes viewers on a trip to explore the world of advertising on Madison Avenue in New York City in the 1960s. The show not only boasts a stellar ensemble cast but also surprises viewers with an array of captivating cameos and small roles played by well-known actors.
From established Hollywood stars to rising talents, Mad Men showcases a revolving door of familiar faces in unexpected places throughout its seven-season run. These fleeting but unforgettable performances give the Mad Men universe fresh energy, delighting fans with unexpected surprises and adding to the already rich tapestry of characters in the show.
10 Danny Strong
Danny Strong, who is widely known as a writer for shows such as Dopesick, Empire, and Game Change, and as Doyle McMaster in Gilmore Girls, also appeared in Mad Men’s fourth season as Danny Siegel, an eager and somewhat bumbling copywriter. Danny's arrival at Sterling Cooper Draper Pryce is marked by his enthusiasm and a touch of naivety, providing a humorous contrast to the jaded and seasoned ad executives.
Strong's portrayal of Danny Siegel is a testament to his versatility as an actor, infusing the character with a mix of charm and awkwardness. Moreover, his brief but memorable stint in the Mad Men universe adds a delightful and entertaining dimension to the show's ensemble cast.
9 Larisa Oleynik
Larisa Oleynik, best known for her roles in beloved '90s shows like The Secret World of Alex Mack and 10 Things I Hate About You, made a delightful guest appearance in Mad Men as Cynthia Cosgrove, the wife of Ken Cosgrove (Aaron Staton), one of the agency's account executives.
Her character's interactions with Ken and the other denizens of the advertising agency provided a glimpse into the personal lives of these characters beyond the boardroom. Despite her little time on the show, her appearance is nevertheless noteworthy and a welcome addition to the ensemble cast of the series.
8 Bess Armstrong
Known for her roles in Jaws 3-D, My So-Called Life, Nothing in Common, and The Four Seasons, Bess Armstrong‘s appearance on Mad Men may easily be overlooked. She portrayed Jane Sterling's (Peyton List) psychiatrist Catherine Orcutt in Season 5 of the show.
Moreover, during her limited screen time, Dr. Orcutt also infamously hosted a gathering where Roger (John Slattery) had his first acid trip. Consequently, even if she isn't a regular, her presence creates a lasting impression.
7 Zosia Mamet
Zosia Mamet, known for her roles in hit series like Girls, made a delightful appearance in Mad Men. In the series, she portrayed Joyce Ramsay, a character who provided a fresh and unconventional perspective on the world of Madison Avenue. Joyce is an art enthusiast and friend of the agency's avant-garde creative team, adding a touch of bohemian spirit to the show.
Mamet's portrayal of Joyce Ramsay brought a unique charm and energy to the series. Additionally, although only made an appearance in five episodes, Mamet provided complexity and mystery to the Mad Men world, making a lasting impression on viewers.
6 Colin Hanks
Left indelible marks on numerous projects such as King Kong, Orange County, Untraceable, and The House Bunny, Colin Hanks is an actor known for his versatile roles. Hanks appeared in Mad Men as Father John Gill, a priest who becomes invested in Peggy Olson’s (Elisabeth Moss) life. Father Gill's appearance explored religious, moral, and ethical issues for both Peggy and the people in her environment.
Moreover, Hanks' performance as Father Gill brought a mix of gravitas and vulnerability to the character. His presence on the show highlighted the challenges of reconciling faith with the ever-changing societal norms of the era. Therefore, Hanks made a significant addition to the show, which continues to stand out in the show's diverse cast of characters.
5 Anna Camp
Anna Camp, who is mostly known for her role in Pitch Perfect and The Help, made a memorable appearance in the show as Bethany Van Nuys, a young and glamorous socialite who is introduced to Don by Roger and Jane in Season 4 premiere.
Bethany always looked stunning and exuded charming confidence, but sadly, their relationship ended when Don got overly obsessed with work. Camp's performance as Bethany Van Nuys was nothing short of charming and her presence brought a fresh and delightful energy to the show.
4 Alexis Bledel
Fans of Gilmore Girls will instantly recognize Alexis Bledel who appeared in Mad Men’s Season 5 for a three-episode arc as Beth Dawes, a mysterious housewife who was involved in the life of Pete Campbell, played by Vincent Kartheiser. Even though she and Pete were both married, they started having an affair, and Pete fell head over heels for her.
Sadly, their romance was broken up when Beth entered the hospital for electroshock treatment and promptly forgot about their time together. Bledel plays a different character in Mad Men than she did in Gilmore Girls, giving viewers a change of pace and showcasing her acting versatility.
3 Harry Hamlin
Mostly known for his works on Clash of the Titans, L.A. Law, and Movie Movie, Harry Hamlin made a notable appearance in Mad Men as Jim Cutler, one of the senior partners at Sterling Cooper & Partners. Jim is introduced during a pivotal period in the agency's history, adding a layer of intrigue and power dynamics to the show.
Jim Cutler is shrewd, ambitious, and unapologetic in his pursuit of the agency's success. The portrayal of Hamlin nails the essence of a brutally competitive executive navigating the 1960s advertising industry's ever-changing terrain. He is a fascinating addition to the program and can't help but excite fans of his earlier works when he shows up.
2 Linda Cardellini
Known for different fandoms in different roles, Linda Cardellini is recognizable for her works in movies and shows such as Avengers: Age of Ultron, The Curse of La Llorona, and Dead to Me. She appeared in Season 6 of Mad Men as Sylvia Rosen, a character who quickly captures Don Draper’s attention.
After saying "I do" to Megan, fans all hoped that Don could finally make this marriage work. However, in the Season 6 premiere, viewers quickly saw that our protagonist simply couldn't resist Sylvia, his next-door neighbor. She continued this relationship with Don during Season 6 and made one more cameo with her husband in Season 7 while they were both in the same elevator.
1 Rosemarie DeWitt
Rosemarie DeWitt is an actress known for Poltergeist,Your Sister's Sister, and Rachel Getting Married, graced the world of Mad Men with her captivating role of Midge Daniels, an artist who becomes entangled in the enigmatic world of Don Draper. Midge is a breath of new air, reflecting the counterculture of the 1960s and questioning the stereotypical gender norms of the time.
With her free-spirited demeanor and artistic sensibilities, DeWitt's Midge serves as a reminder of the societal shifts taking place during that transformative decade, and her interactions with Don provide a glimpse into his enigmatic past and the challenges of his personal life.
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