Patrick Dempsey's 7 Best TV & Film Roles

Patrick Dempsey became a major heartthrob in the mid-2000s following his casting in Grey’s Anatomy. On the long-running series, he was widely referred to as “McDreamy,” and this title has evidently stuck. Almost a decade after leaving Grey’s, fans continue to refer to him with the nickname, and for those who forgot, there’s a newfound interest in the actor’s devilishly handsome looks. PEOPLE recently crowned Dempsey the Sexiest Man Alive in their yearly poll. At 57, he is one of the oldest men to achieve the coveted title, proving the legacy of McDreamy continues to live on. With a horde of interesting film and television roles in his catalog, let’s look at seven times the actor nailed his performances on screen.

Based on the true story of Erin Gruwell, Freedom Writers follows the dedicated teacher who inspires her at-risk school students to overcome adversity and intolerance through the power of writing. As Erin transforms her divided and troubled class, she introduces them to The Diary Of Anne Frank. Furthermore, she encourages the students to share their own stories and break the cycle of violence and prejudice in their lives. In this inspirational and powerful drama film, Dempsey takes on the role of Scott Casey, Erin’s husband who does not support her endeavors and ultimately divorces her. Dempsey’s ability to handle emotionally charged narratives with grace becomes evident in this 2007 movie. Even though his character was not one to root for, his acting was stellar. 

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Patrick Dempsey is also widely known for his charming rom-com roles. In Made Of Honor, he took on the role of Tom, a perennial bachelor and playboy. His character soon realizes he is in love with his best friend, Hannah. However, when Hannah becomes engaged to someone else, Tom is unexpectedly asked to become her maid of honor. Tom decides to seize the opportunity but soon finds himself struggling to accept his true feelings. Here, Patrick Dempsey expertly brought his character to life and gave this role the charm it needed. Although the film wasn’t critically acclaimed, it’s become a favorite among audiences. 

In the whimsical Disney film Enchanted, Patrick Dempsey took on the role of Robert Philip, a cynical divorce lawyer. The story follows Giselle, a fairy-tale princess who is banished to modern-day New York by an evil queen. As Giselle navigates the unfamiliar urban landscape, she encounters a divorce lawyer named Robert who helps her settle in the regular world. Dempsey’s charm and comedic timing helped deliver the heartfelt romantic narrative. Furthermore, his grounding performance created a delightful contrast to the fantastical elements of the film. Overall, he showed his ability to seamlessly transition between genres. 

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In Sweet Home Alabama, Dempsey played the dashing and successful Andrew Hennings. The rom-com revolves around Melanie Carmichael, a successful fashion designer in New York City, who is engaged to Andrew, the city’s most desirable bachelor. The only problem is she is legally married to her high school sweetheart, Jake. Melanie returns to her small Southern hometown in Alabama to get a much-needed divorce. Here, Dempsey deftly portrayed a wealthy and likable character that won Melanie’s heart. His performance also made him an unforgettable part of the film’s love triangle.

Showcasing his versatility in the horror genre, Patrick Dempsey takes on the role of Detective Mark Kincaid in the third installation of the Scream franchise. Scream 3 follows the return of the Ghostface killer, who targets the cast and crew of the fictional film Stab 3. Sydney Prescott becomes the target once again as she tries to uncover the identity of the masked murderer. Dempsey’s character is a detective who is assigned to the Ghostface case in the film. His performance added a layer of intensity to the satirical slasher film.

In this 80s teen comedy, Patrick Dempsey is the lovable high school nerd Ronald who pays the popular girl Cindy Mancini to be his girlfriend in a quest to elevate his social status. As the social experiment unfolds, the two begin to uncover feelings within themselves. The film’s success contributed to Dempsey's rise in the '80s teen movie scene. It also laid the groundwork for the diverse career that would follow. The actor’s performance filled the film with humor and heart, winning him a Young Artist Award for Best Young Actor in a Motion Picture. 

Undoubtedly, Dempsey’s most iconic role is playing Dr. Derek Shepherd in the hit medical drama series Grey’s Anatomy. The long-running drama series follows the lives, relationships, and careers of surgical interns, residents, and attending physicians at Grey Sloan Memorial Hospital. Dempsey’s portrayal of the talented and charismatic neurosurgeon captivated audiences for over a decade. His on-screen chemistry with Ellen Pompeo, who plays Meredith Grey, also became a defining element of the show. Dr. Derek “McDreamy” Shepherd remains an unforgettable character in modern television. 

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