Patrick Dempsey's 10 Best Movie and TV Show Performances (2024)

Patrick Dempsey has carved out a remarkable journey through Hollywood. Since his early days in the industry in the mid-1980s, Dempsey has gradually built a name for himself. Thanks to his undeniable charm, determination and talent, his career has become a combination of roles that have captured the hearts of the audiences. He’s been in romantic comedies but has also performed in dramatic roles. A testament to his versatility as an actor, breathing life into diverse characters.

Not only has he shown his talent in the world of entertainment as an actor, but also as a producer. In addition to his achievements in the industry, Dempsey is a passionate race car driver, proving that his talent can go beyond. Now that he’s being crowned as People Magazine's Sexiest Man Alive of 2023, it’s time to take a trip through his filmography. After being part of all sorts of movies and TV shows, people laugh, cry, and fall in love with his portrayals of different characters. So, let’s dive into 10 of his best performances and see why he's a Hollywood star that's here to stay.

10 Made of Honor (2008)

Made of Honor

PG-13

Release Date

April 30, 2008

Director

Paul Weiland

Cast

Patrick Dempsey , Michelle Monaghan , Kevin McKidd , Kadeem Hardison , Chris Messina , Richmond Arquette

Main Genre

Comedy

Made of Honor is a 2008 rom-com that tells a charming story about love and friendship. Patrick Dempsey takes the lead as Tom, a lifelong playboy who unexpectedly finds himself falling in love with his best friend, Hannah (Michelle Monaghan). However, Tom’s world is turned upside down when she announces her engagement, and to add more drama, she requests him to be her maid of honor. Directed by Paul Weiland, this film tries to navigate a rollercoaster of emotions and the complexities of their relationship, all while blending humor and heartwarming moments.

Why is it One of Dempsey’s Best Performances?

Dempsey’s portrayal of Tom in Made of Honor showcases his versatility beyond his renowned dramatic roles. His charismatic presence, comedic timing, and charm not only elevate the movie, but it also brings depth to the character, making people relate to Tom’s situation. Even though the film didn’t receive a positive critical response, both critics and audience admit that Dempsey’s sharp performance is one of the film’s standout features, alongside his on-screen chemistry with Monaghan.

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9 Sweet Home Alabama (2002)

Sweet Home Alabama

PG-13

See Also

Patrick Dempsey | Rotten TomatoesEvery Single Patrick Dempsey Movie, Ranked From Worst to BestPatrick Dempsey's most memorable movie and TV rolesThe 10 best Patrick Dempsey movies and TV shows

Release Date

September 27, 2002

Director

Andy Tennant

Cast

Reese Witherspoon , Patrick Dempsey , Josh Lucas , Candice Bergen , Fred Ward , Melanie Lynskey

Main Genre

Comedy

In the town of Pigeon Creek, Sweet Home Alabama (2002) unfolds the story of Melanie (Reese Witherspoon), a New York City fashion designer who has a hidden past in her hometown that she must face after getting engaged to Andrew (Patrick Dempsey). The truth is that she’s still married to Jake (Josh Lucas), her childhood sweetheart. This story dives into the romantic turmoil between them and how it affects her new relationship with Andrew. Directed by Andy Tennant and written by C. Jay Cox, it received mixed critical responses, but it was a success at the box office, with more than $180 million by the end of its run.

Why Does it Make the List?

One might argue that the narrative was crafted in a way that Melanie’s choice between the two candidates was kind of obvious. Following the usual archetype of a rom-com, the millionaire fiancé who tries to separate the childhood sweethearts is easy to cast off. However, because of Dempsey’s performance, the dismissal of his character is a challenge to overcome for the audience. Dempsey’s Andrew is a character that embodies the qualities of a devoted partner who sees Melanie’s beyond her New York façade, embracing her for who she truly is. With this, Dempsey showcased that he can convey depth and sincerity in his performances, and, by the end, we were all rooting for Andrew.

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8 Scream 3 (2000)

Scream 3

R

Release Date

February 3, 2000

Director

Wes Craven

Cast

Liev Schreiber , Beth Toussaint , Roger Jackson , Kelly Rutherford , Neve Campbell , Courteney Cox

Main Genre

Horror

Following the Scream franchise, Scream 3 is a horror film from 2000, directed by Wes Craven. This third installment dives into the return of Ghostface as a new series of murders haunt the production of the fictional film “Stab 3”. The film centers on Sidney Prescott (Neve Campbell), as she becomes the target of the assassin once again. Like its previous movies, Scream 3 is a combination of meta-horror blended with suspense and self-aware humor, making it a fitting addition to this iconic horror franchise. One that’s part of Patrick Dempsey’s filmography, since he plays the role of Mark Kincaid, a detective who's following the recent murders and wants to protect Sidney.

Why it's One of His Best

Dempsey is well known for his participation in comedies since he started his career back in the 1980s, so he fit right in with the characteristic tone of this franchise, which’s known for its satire within the horror genre. Even though he doesn’t have a main role in Scream 3, his portrayal of Kincaid was well received by the audience, as he managed to perform suspiciously enough to keep the audience questioning if he could be the masked killer or not. Combining and balancing the suspense with lighter comedic moments, as expected from these films.

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7 Disenchanted (2022)

enchanted 2

Director

Adam Shankman

Cast

Amy Adams , James Marsden , Patrick Dempsey

Main Genre

Adventure

Disenchanted is the 2022 sequel to the successful live-action Enchanted (2007). Set ten years after the previous one, Giselle (Amy Adams) and Robert (Patrick Dempsey) decide to move their family to Monroeville, a suburban town, as the hasty life in New York is starting to get to them. However, the move was not what they expected, as they were all struggling to adapt to their new routine. Therefore, Giselle decided to use a wish-granting wand to turn their lives into a perfect fairy tale. But she didn’t expect that she’d become a villain, and both the real world and Andalasia would be in danger.

Why it Makes the List

Dempsey’s ability to portray the vulnerabilities of Robert, and later going into a complete transformation of his character’s personality, is a testament to his acting skills and versatility. And let’s not forget to add the integration of his singing and dancing, going far away from his role in the first film. His characterization of Robert undergoes a significant shift, going from skepticism to embracing the whimsical personalities of his peers. Showcasing the way he can embrace and adapt to any role.

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6 Can’t Buy Me Love

From his early roles, Can’t Buy Me Love (1987) is a teen rom-com that follows the story of Ronald (Patrick Dempsey), a nerd with a golden heart who pays a popular cheerleader, Cindy (Amanda Peterson), to pretend to be his girlfriend for a month, in an intent to boost his social status at school. As the plot unfolds, he starts to gain more confidence and goes from an insecure person to a self-confident young man. But he also realizes that money can’t buy true love and happiness. The film goes into an exploration of themes such as friendship, identity, and the importance of being oneself.

Why Is it One of His Best Performances?

Even if this role might feel different from his most recent characters, Patrick Dempsey’s portrayal of Ronald fits perfectly with what’s expected of a teenage romance. He showcased a perfect balance between the awkwardness of his fake romance and the genuine feelings they start to develop. Also, the transformation that Ronald faced throughout the movie is a testament to Dempsey’s acting skills. And even if the movie got mixed opinions among the critics, his performance was well received. It even got him a Young Artist Award for Best Young Actor in a Motion Picture in Comedy.

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5 Bridget Jones's Baby (2016)

Bridget Jones Baby

R

Release Date

September 14, 2016

Director

Sharon Maguire

Cast

Renée Zellweger , Colin Firth , Patrick Dempsey , Jim Broadbent , Celia Imrie , James Callis

Main Genre

Comedy

Once again, let’s dive into one of Dempsey’s roles in a romantic comedy: Jack Qwant in Bridget Jones’s Baby (2016). This is the third installment of these movies that center around the lovable but clumsy Bridget Jones (Renée Zellweger). On this occasion, now in her 40s, she found herself unexpectedly pregnant and uncertain about the father’s identity. Directed again by Sharon Maguire, the story of Bridget is, as always, filled with humor and her signature extravaganzas, but at the same time it explores the complexities of love, relationships, and the journey to parenthood in a unique and delightful way.

Why it Belongs Here

Entering an already established rom com franchise, with such a lovable character like Bridget Jones, can’t be an easy task for anyone. However, Dempsey’s characteristic way of adding charisma, wit and sincerity to his characters earns the heart of every fan of this story. He added his charming and affable qualities to Jack, helping create a dynamic and engaging presence on the scene. His chemistry with Zellweger added a new layer of excitement, injecting a fresh energy into the franchise. As well as providing an interesting alternative to Colin Firth’s character, Mark Darcy.

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4 With Honors (1994)

During With Honors, we follow Monty Kessler (Brendan Fraser), a Harvard student who loses his thesis in the university library’s basement. A homeless man named Simon Wilder (Joe Pesci) is the one who found it, and, after some encounters with the law, both Monty and Simon start an unexpected friendship. This film blends drama and comedy in a perfect balance, exploring themes of friendship, compassion, all while deepening societal issues such as homelessness and the importance of success. Directed by Alek Keshishian and written by William Mastrosimone, this 1997 film is full of heartwarming moments and poignant reflections about life.

Why it's One of His Best

Patrick Dempsey doesn’t have a central role in this movie. He plays Everett Calloway, a playboy DJ who happens to be Monty Kessler’s roommate. As part of the supporting cast, Dempsey’s Everett contributes to the dynamics of the film. His character is crafted to be a privileged, and even a somewhat arrogant, student. This added so much depth to the exploration of social and economic differences between Simon and the other characters. Undoubtedly, Dempsey was able to deliver a meaningful performance that perfectly aligned with the expectations associated with this character.

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3 Enchanted (2007)

Enchanted

PG

Release Date

November 21, 2007

Director

Kevin Lima

Cast

Patrick Dempsey , Amy Adams , Timothy Spall , Susan Sarandon , Idina Menzel , James Marsden

Main Genre

Comedy

Enchanted is a Disney live-action film from 2007 that tells the story of Giselle (Amy Adams), a fairy-tale princess who's transported from her animated kingdom into the modern-day real world. She must navigate through the complexities of real life, as her infectious optimism and fairy-tale perspective clash with this unfamiliar setting full of cynicism. Along the way, she becomes entangled in the lives of Robert (Patrick Dempsey), a divorce lawyer, and his daughter Morgan. The whole story is a heartwarming tale that explores the significance of love and friendship. But most importantly, the contrast between the ideals set by fairy tales, and the reality of the world.

Why it Makes the List

In Enchanted, Dempsey became an unconventional Disney Prince, and people absolutely loved it. His role is pivotal to the film’s success, as he portrays the relatable anchor that keeps the story on the ground. Robert showcases a delightful fusion of humor with sincerity, creating a genuine connection with the audience. Besides, his on-screen chemistry with Amy Adams is undeniable, bringing an endearing quality to this romantic comedy. And despite being faced with the challenge of the contrasting personalities of his co-stars’ characters, Dempsey rose to the occasion. In that way, Robert became a beloved character among the fans.

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2 Freedom Writers (2007)

Freedom Writers

PG-13

Release Date

January 5, 2007

Director

Richard LaGravenese

Cast

Hilary Swank , Patrick Dempsey , Scott Glenn , Imelda Staunton , April L. Hernandez , Mario

Main Genre

Biography

The 2007 American Drama directed by Richard LaGravenese, Freedom Writers, is a film that follows the story of Erin (Hilary Swank), an English teacher assigned to work with at-risk students in a high school that’s racially divided and marked by gang conflicts. She must face challenges as she tries to connect with her students, teenagers who come from different backgrounds and doesn’t have any trust or respect for authority figures. So, Erin dedicates herself to breaking down the racial barriers by using different kinds of teaching methods that help her inspire her students to overcome their difficulties. This is a story based on real events that explores the power of education. In this whole plot, Patrick Dempsey plays Scott Casey, Erin’s husband.

Why it Makes the List

In Freedom Writers, Patrick Dempsey shows his chameleon-like ability to immerse himself in diverse roles, adapting to the director’s vision of the film. We are accustomed to his charismatic rom-com characters, but as Scott Casey, he embodies a selfish, unsatisfied husband who's disappointed at the unconventional teaching methods his wife employs. Perfectly reflecting his disdain and the complexities of their marriage dynamic. This showcasing of his distinctive acting style underscores his commitment to portraying characters in the most authentic way.

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1 Grey’s Anatomy

Talking about Patrick Dempsey's best performances without mentioning Grey’s Anatomy is impossible. This American medical drama is the peak of Dempsey’s career. A story that follows the lives of surgical interns, residents, and attending at the Seattle Grace Hospital (later known as Grey Sloan Memorial). This show premiered back in 2005, created by Shonda Rhimes, and starring Patrick Dempsey as its male lead, the neurosurgeon Dr. Derek Shepherd. Grey’s Anatomy has become one of the longest TV medical dramas and has been praised over the years for its compelling stories, earning multiple awards and nominations along the way.

Why it's Patrick Dempsey's Best

Even if this isn't his first or last role, Patrick Dempsey's most iconic portrayal over the years is in Grey’s Anatomy. As the charismatic Dr. Derek Shepherd (a.k.a. McDreamy), Dempsey earned the hearts of many fans across the world. His character’s journey from a one-night stand with Meredith, to a profound love story, established him as a captivating romantic lead. His portrayal of Derek earned him multiple nominations at the Screen Actors Guild Awards and the Golden Globes. His performance is a testament to his enduring talent, as he had to navigate the difficult challenges of his character. He has a charm that left a lasting impact on this TV show, even after his departure in season 11, when viewers were heartbroken by his death.

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