Best Patrick Dempsey Movies and TV Shows Ranked

Patrick Dempsey has an irresistible charm and good looks, which persists across all of his movies and TV shows. He gained notoriety in the late 1980s with movies like Can’t Buy Me Love but rose to exceptional fame with his crucial role in the hit TV show Grey’s Anatomy

The best Patrick Dempsey movies and TV shows give a glimpse of his acting skills and lovable personality. Fans of Dempsey might expect his most impactful movies and TV shows to focus on rom-coms, but he has so much more to offer than that. Check out the best Patrick Dempsey movies and TV shows ranked below. 

1. Grey’s Anatomy (2005-2015)

Grey's Anatomy (2005)
Image Credit: Shondaland.

Patrick Dempsey skyrocketed to fame with the masterful and unforgettable hospital ABC drama Grey’s Anatomy. But that only represents half the story. Dempsey himself put on the best performance of his career with his lengthy, emotional, and brilliant portrayal of Dr. Derek Shepherd until he left the show in 2015. 

2. Enchanted (2007)

Patrick Dempsey-Enchanted
Image Credit: Walt Disney Studios Motion Pictures.

No other Patrick Dempsey movies showcase the charm and talent of the man as well as this Disney live-action and animated hybrid flick. The music, set pieces, and magical take on fairy tale tropes deliver one of the highest quality takes on the princess and her prince but with a modern Manhattan twist. 

3. Freedom Writers (2007)

Patrick Dempsey, Freedom Writers
Image Credit: Paramount Pictures.

This empowering and inspirational drama follows a teacher, played by the exceptional Hilary Swank, as she tries to get her inner-city students in Los Angeles to care about learning. Dempsey plays a solid supporting role as Scott, but Swank and her class of talented teens stand out in this powerful movie. 

4. Bridget Jones’s Baby (2016)

Bridget Jones’s Baby, Patrick Dempsey
Image Credit: Giles Keyte / Universal Pictures.

The third iteration of this beloved Renée Zellweger franchise came back from the dead long after the first two movies. Even so, it somehow comes close to capturing the feel and style of the first couple of movies with a middle-aged touch. Zellweger and Dempsey have impressive onscreen chemistry with one another. 

5. Sweet Home Alabama (2002)

Sweet Home Alabama, Candice Bergen, Reese Witherspoon, Patrick Dempsey
Image Credit: Touchstone Pictures.

Patrick Dempsey has a more welcome villainous role in this genre-defining rom-com that showcases his charm in a different way. He plays the rich city boy who competes for the love of Reese Witherspoon’s Melanie as she returns to her small country hometown to end things with her husband.

6. Brother Bear 2 (2006)

Brother Bear 2, Patrick Dempsey, Mandy Moore
Image Credit: Walt Disney Home Entertainment.

Patrick Dempsey’s takeover of the role of Kenai in this Disney sequel feels a bit off compared to the original, but the magical adventure he goes on with Mandy Moore’s Nita makes up for that. It doesn’t quite live up to the first movie, but it still feels great in its own right. 

7. Iron Jawed Angels (2004)

Iron Jawed Angels, Patrick Dempsey, Hilary Swank
Image Credit: HBO Films.

This powerful movie takes a look at the women’s suffrage movement in an impactful and unfiltered way. Hilary Swank takes command of the lead role as Alice Paul and delivers a memorable performance, leading to her even better activist movies later. 

8. Devils (2020-2022)

Devils, Patrick Dempsey
Image Credit: Sky Studios.

Patrick Dempsey carries this otherwise missable TV drama about a man discovering a worldwide financial conspiracy. The smart budget results in a show that looks fantastic but could use some work in the writing department. It improves, though, if fans make it to the better second season. 

9. Can’t Buy Me Love (1987)

Can’t Buy Me Love, Patrick Dempsey
Image Credit: Buena Vista Pictures Distribution.

Patrick Dempsey gained his first significant group of fans with this teen rom-com about a nerd who convinces the popular cheerleader to act like his girlfriend. Its writing feels a bit outdated in the modern age, but the chemistry between Dempsey and Amanda Peterson sells the idea.

10. Fast Times (1986)

Fast Times
Image Credit: Universal Television.

This TV series adaptation of the incredible Fast Times at Ridgemont High offers an intriguing look at one of the earliest roles in Dempsey’s career. He plays the likable Mike well, but the series only released seven episodes due to its failed challenge to come close to the fantastic original movie. 

11. Disenchanted (2022)

Disenchanted, Patrick Dempsey
Image Credit: Alex Bailey / Disney Enterprises, Inc.

This long-awaited sequel to the beloved Disney modern musical classic fails to deliver any of the magic of the original. It feels like the safest sequel attempt as Amy Adams’ Giselle once again learns familiar lessons as she navigates a new, less exciting setting of suburban life.

12. Scream 3 (2000)

Scream 3, Patrick Dempsey
Image Credit: Dimension Films.

The third movie in this beloved slasher thriller series offers one of the weaker plots in the franchise. One of the brighter spots of this entry remains Patrick Dempsey in his suspicious but charming role of Detective Mark Kincaid, who needs to return someday to the series. 

13. Valentine’s Day (2010)

Valentine’s Day, Patrick Dempsey
Image Credit: Warner Bros. Pictures.

This holiday rom-com follows a packed set of stars and their tangled web of romance on Valentine’s Day. The impressive cast leads to solid and memorable performances, but the overstuffed plot could use some work on balancing the numerous storylines better. 

14. Coupe de Ville (1990)

Coupe de Ville, Patrick Dempsey, Arye Gross
Image Credit: Universal Pictures.

This straightforward and simplistic comedy sticks to its simple premise and handles it pretty well. Patrick Dempsey plays one of three brothers who go on a cross-country journey together to bring a car for their mother’s birthday. This leads to ridiculous and relatable spats as the siblings battle with one another on the road trip. 

15. With Honors (1994)

With Honors, Brendan Fraser, Patrick Dempsey, Josh Hamilton, Moira Kelly
Image Credit: Warner Bros.

The beautiful premise of a graduate student becoming best friends with an older homeless man sounds fantastic. However, the execution suffers from a lack of class and care. Even still, Brendan Fraser and Joe Pesci offer some emotional and wonderful scenes.

16. Winning: The Racing Life of Paul Newman (2015)

Winning The Racing Life of Paul Newman, Patrick Dempsey
Image Credit: Orion Pictures.

Patrick Dempsey plays a leading role in this biographical documentary about Paul Newman and his 35-year history in racing. The all-star cast, with the likes of John Lasseter and Jay Leno, help bring this unique story to life. 

17. The Emperor’s Club (2002)

The Emperor’s Club, Kevin Kline, Patrick Dempsey
Image Credit: Universal Pictures.

This movie represents yet another life lesson teen drama Dempsey stars in, but it also represents the weakest of the bunch. Its lessons don’t quite hit home as well as in other similar films like Freedom Writers, though a notable performance from Kevin Kline in the lead role makes it worth a potential watch. 

18. Lucky 7 (2003)

Lucky 7, Patrick Dempsey
Image Credit: Lions Gate Television.

Patrick Dempsey plays the likable Peter, the potential fated man of Kimberly Williams-Paisley’s Amy’s dreams. The budget feels a bit too low, even for a 2003 flick, but the predictable storyline at least offers some solid performances from its two leads. 

19. Loverboy (1989)

Loverboy, Patrick Dempsey
Image Credit: TriStar Pictures.

This awkward rom-com has a problematic premise, which didn’t age too well. Patrick Dempsey plays a pizza delivery boy who soon finds himself offering quite different services to his customers. That said, Dempsey fans may find some enjoyment in the occasional laughs.

20. Transformers: Dark of the Moon (2011)

Transformers Dark of the Moon, Patrick Dempsey
Image Credit: Paramount Pictures.

The visual effects of this third Michael Bay Transformers movie look terrific, but the film lacks any substance elsewhere. The story feels forgettable and bloated alongside its recognizable cast, where the script does none of them justice. 

21. Some Girls (1988)

Some Girls, Jennifer Connelly, Patrick Dempsey, Ashley Greenfield, Sheila Kelley
Image Credit: MGM/UA Communications Co.

This early R-rated rom-com movie in Dempsey’s career feels a bit too all over the place. It starts with his breakup with his girlfriend, played by Jennifer Connelly, and soon leads to many different sub-stories with his ex’s sisters, her grandmother, and her father. Its general lack of direction holds back the otherwise potential chemistry. 

22. Made of Honor (2008)

Made of Honor, Patrick Dempsey
Image Credit: Sony Pictures Releasing.

Dempsey showcases his charm as always, but that doesn’t quite do enough to save this epitome of cliché and stereotypical rom-com flicks. Dempsey plays Tom, a rich snob who realizes he loves his best friend when her wedding day approaches.