The Best Patrick Dempsey Movies

Ranker Film
Updated August 11, 2023 2.1K votes 508 voters 44.9K views
Over 500 Ranker voters have come together to rank this list of The Best Patrick Dempsey Movies
Voting Rules
Vote for your favorite movies, regardless of critic reviews or how big the role was.
Latest additions: Disenchanted
Most divisive: Coupe de Ville

Patrick Dempsey's career has been an impressive one, and now movie fans everywhere have come together to vote on his best and worst films. From his iconic roles in Can't Buy Me Love and Enchanted, to more challenging dramas such as Outbreak and Freedom Writers - there is something for everyone on this list. What makes these rankings so interesting though, are the fan's perceptions of each movie based on its performances, writing, direction and overall entertainment value.

No matter what type of Dempsey film you're looking for - light-hearted or emotionally gripping - it can be found here. In fact if your favorite isn't where you think it should be? It's up to you to change that. The only way we'll find out which films truly showcase Dempsey's talents as an actor is by having all votes counted.

So whether you were a fan of McDreamy back in the day or just discovered him recently, get ready for some fun discussions with fellow movie buffs over Patrick Dempsey’s top films.

Ranked by
  • Can't Buy Me Love
    1

    Can't Buy Me Love

    Patrick Dempsey, Amanda Peterson, Courtney Gains
    148 votes
    • Released: 1987
    • Directed by: Steve Rash
    In Can't Buy Me Love, Ronald Miller (Patrick Dempsey) is a high school nerd yearning for popularity. Cindy Mancini (Amanda Peterson), the school's cheerleader queen, unexpectedly becomes his ticket to the in-crowd. When her mother's expensive outfit gets ruined, desperate Cindy agrees to Ronald's proposition: he will pay for the dress if she pretends to be his girlfriend. As they navigate through teenage hierarchies and social expectations, this 80s teen comedy-drama explores themes of acceptance, authenticity, and love beyond superficiality. The movie boasts engaging performances from its leads and offers a charmingly nostalgic trip back to high school life in the Reagan era.

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  • Enchanted
    2

    Enchanted

    Amy Adams, Patrick Dempsey, James Marsden
    116 votes
    • Released: 2007
    • Directed by: Kevin Lima
    Enchanted, a delightful blend of live-action and animation, introduces us to the world of Giselle (Amy Adams), a fairytale princess abruptly thrust into modern-day New York City by the conniving Queen Narissa (Susan Sarandon). Struggling to navigate this strange new landscape, she crosses paths with Robert (Patrick Dempsey), a cynical divorce lawyer. As their worlds intertwine, they find themselves questioning their perceptions of love and happiness. A standout feature is its Oscar-nominated music score. Enchanted seamlessly weaves humor, romance and adventure into a film that appeals to all ages.

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  • Made of Honor
    3

    Made of Honor

    Patrick Dempsey, Michelle Monaghan, Kevin McKidd
    108 votes
    • Released: 2008
    • Directed by: Paul Weiland
    Always shy of commitment, Tom (Patrick Dempsey) lives as a serial dater. Hannah (Michelle Monaghan), his best friend, has wanted to marry and now has found Mr. Right -- just as Tom realizes he really loves Hannah. When she asks him to be in her bridal party, Tom seizes the opportunity to prevent the nuptials and woo her himself.

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  • Sweet Home Alabama
    4

    Sweet Home Alabama

    Reese Witherspoon, Josh Lucas, Patrick Dempsey
    111 votes
    • Released: 2002
    • Directed by: Andy Tennant
    In Sweet Home Alabama, Melanie Carmichael (Reese Witherspoon), a successful New York fashion designer, prepares for her wedding to the city's most eligible bachelor, Andrew Hennings (Patrick Dempsey). However, her past in rural Alabama holds an unresolved issue - a husband, Jake Perry (Josh Lucas), who refuses to divorce her. The romantic comedy-drama unfolds as Melanie returns to her roots, navigating through a web of old friendships and past love. It is a tale of self-discovery and second chances that emphasizes the significance of one's origins amidst the dazzle of success and city life.

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  • Lucky 7
    5

    Lucky 7

    Patrick Dempsey, Kimberly Williams-Paisley, Gail O'Grady
    49 votes
    • Released: 2003
    • Directed by: Harry Winer
    Lucky 7 is a 2003 made-for-TV film starring Patrick Dempsey and Kimberly Williams.

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  • Freedom Writers
    6

    Freedom Writers

    Hilary Swank, Patrick Dempsey, Scott Glenn
    43 votes
    • Released: 2007
    • Directed by: Richard LaGravenese
    A dedicated teacher (Hilary Swank) in a racially divided Los Angeles school has a class of at-risk teenagers deemed incapable of learning. Instead of giving up, she inspires her students to take an interest in their education and planning their future. She assigns reading material that relates to their lives and encourages them all to keep journals.

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