The 40+ Best Patrick Dempsey Movies
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1Patrick Dempsey, Amanda Peterson, Courtney GainsIn 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.More Can't Buy Me Love
- #120 of 399 onThe Best Movies Of The 1980s, Ranked
- #87 of 232 onThe Best '80s Comedy Movies, Ranked
- #224 of 278 on'Old' Movies Every Young Person Needs To Watch In Their Lifetime
2Amy Adams, Patrick Dempsey, James MarsdenEnchanted, 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.More Enchanted- #454 of 769 onThe Most Rewatchable Movies
- #101 of 452 onThe 400+ Best Animated Kids Movies
- #46 of 204 onMusical Movies With The Best Songs
3Patrick Dempsey, Michelle Monaghan, Kevin McKiddAlways 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.More Made of Honor
4Reese Witherspoon, Josh Lucas, Patrick DempseyIn 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.More Sweet Home Alabama- #264 of 769 onThe Most Rewatchable Movies
- #10 of 136 onThe 100+ Best Movies For Date Night
- #45 of 152 onThe Best Movies of 2002
5Patrick Dempsey, Kate Jackson, Robert GintyDelivering pizzas doesn't pay much -- especially when Randy Bodek (Patrick Dempsey) needs to earn enough to fund next semester's college tuition. During a routine delivery, however, Randy meets a sexy older woman named Alex (Barbara Carrera). The pair become lovers, and soon she's recommending Randy's services to all her unhappily married friends -- just order a pizza with extra anchovies and tip well. But, as Randy soon learns, life as a professional gigolo can get pretty complicated.More Loverboy- #175 of 232 onThe Best '80s Comedy Movies, Ranked
- #58 of 96 onThe Best '80s Teen Movies, Ranked
- #108 of 127 onThe 100+ Best Sex Comedy Movies
6Patrick Dempsey, Mandy Moore, Wanda SykesThis animated tale finds big bear Kenai (Patrick Dempsey) emerging from hibernation with a ferocious hunger. When he goes to eat some berries with his little brother, Koda (Jeremy Suarez), he encounters his old human friend, Nita (Mandy Moore). She has a pressing problem, though. She wants to get married, but first has to burn her amulet at Hokani Falls. Since Kenai was the one who gave it to Nita, he must accompany her. Together, they head out to the waterfall for a transformative adventure.More Brother Bear 2- #389 of 452 onThe 400+ Best Animated Kids Movies
- #14 of 16 onThe 16 Best Disney Sequels, Ranked By Fans
- #3 of 17 onThe Best Movies About Grizzly Bears
7Patrick Dempsey, Kimberly Williams-Paisley, Gail O'GradyLucky 7 is a 2003 made-for-TV film starring Patrick Dempsey and Kimberly Williams.- 8Jessica Alba, Kathy Bates, Jessica BielIn the ensemble romantic comedy Valentine's Day, love is in the air across Los Angeles. The movie, directed by Garry Marshall, showcases a day in the life of star-crossed lovers and singletons alike. Reed Bennett (Ashton Kutcher) proposes to his girlfriend Morley (Jessica Alba), while Julia Fitzpatrick (Jennifer Garner) discovers her boyfriend is married. Meanwhile, sports reporter Kelvin Moore (Jamie Foxx) and publicist Kara Monahan (Jessica Biel) navigate their careers amidst the holiday chaos. From young love to mature relationships, Valentine's Day explores various facets of love and romance with humor and heart.More Valentine's Day
- #102 of 136 onThe 100+ Best Movies For Date Night
- #297 of 473 onThe 400+ Best Chick Flicks Ever
- #7 of 12 onBest Comedy Movies Streaming on Hulu
9Hilary Swank, Patrick Dempsey, Scott GlennA 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.More Freedom Writers- #32 of 90 onThe 85+ Most Inspirational Movies Of All Time
- #141 of 242 onThe 200+ Best Movies Based On A True Story
- #107 of 139 onThe Best Movies Of 2007
10Patrick Dempsey, Octavia Spencer, Jeffrey TamborFlypaper is a 2011 crime fiction comedy film written by Jon Lucas and Scott Moore, and directed by Rob Minkoff.
11Kelly Preston, Patrick DempseyRun is a 1991 film, directed by Geoff Burrowes. The movie stars Patrick Dempsey and Kelly Preston.
12Dustin Hoffman, Rene Russo, Morgan FreemanIn the gripping film Outbreak, a deadly and highly contagious virus is unleashed in a small California town. The virus, brought to American soil by an African monkey, swiftly turns the peaceful town into a hotbed of contagion. Sam Daniels (Dustin Hoffman), a maverick virologist, races against time to isolate this new pathogen before it spreads beyond control. Assisting him are his ex-wife, Robby Keough (Rene Russo), and his loyal colleague, Casey Schuler (Kevin Spacey). The trio must navigate governmental obstruction, personal tensions, and their own fears in this tense medical thriller. Their mission: halt the outbreak and prevent a potential global catastrophe.More Outbreak- #82 of 125 onThe 100+ Grossest Movies Ever
- #5 of 138 onThe 100+ Best Disaster Movies Of All Time
- #24 of 90 onThe Best Movies Of 1995
13Amy Adams, Patrick Dempsey, James MarsdenGiselle upsets the balance of Andalasia and the real world.
14David Arquette, Neve Campbell, Courteney CoxIn the third installment of the iconic Scream series, Sidney Prescott (Neve Campbell) finds herself once again in the crosshairs of the Ghostface killer. Yet this time, Hollywood is the backdrop. The production of Stab 3, a movie within the movie, becomes an eerie echo of reality as cast members are targeted by an all-too-familiar masked murderer. Gale Weathers (Courteney Cox) and Dewey Riley (David Arquette) return to help unravel a chilling mystery that ties back to their shared past. With director Wes Craven at the helm, Scream 3 intertwines suspense, drama, and self-aware satire in its unique blend of horror and comedy.More Scream 3- #17 of 21 onSmart Ways Dumb Horror Sequels Improve On The Originals
- #17 of 80 onThe Best Teen Horror Movies Of All Time
- #59 of 118 onThe Best Horror Movie Sequels
- 15Shia LaBeouf, Josh Duhamel, John TurturroIn the third installment of the Transformers series, Transformers: Dark of the Moon is a sci-fi action spectacle. The plot centers around the Autobots, led by Optimus Prime (voiced by Peter Cullen), as they discover a hidden spacecraft on the moon and race against time to reach it before their archenemies, the Decepticons. With humanity's fate hanging in the balance, Sam Witwicky (Shia LaBeouf) joins forces with the Autobots once again. This cinematic extravaganza, directed by Michael Bay, showcases stunning visual effects and high-octane action sequences that won it an Academy Award nomination for Best Visual Effects.
16With Honors
Joe Pesci, Brendan Fraser, Moira KellyAcademia meets street smarts when Monty Kessler (Brendan Fraser), a graduate student struggling to finish his program, loses his thesis and finds it in the hands of a homeless man named Simon Wilder (Joe Pesci). Though the two get off on the wrong foot, they become unlikely friends, with Simon teaching Monty some important life lessons. Although Monty's roommates, including his buddy, Everett Calloway (Patrick Dempsey), initially dislike having Simon around, they grow to appreciate him, too.More With Honors- #71 of 85 onThe Best Movies Of 1994
- #50 of 71 onThe 70 Best College Movies
- #37 of 43 on30+ Very Preppy Movies with the Preppiest Characters
17Christian Slater, Patrick Dempsey, Richard GriecoLoosely based on real historical figures, this drama focuses on the empire built by enterprising young criminals Lucky Luciano (Christian Slater) and Meyer Lansky (Patrick Dempsey). Along with Bugsy Siegel (Richard Grieco) and Frank Costello (Costas Mandylor), Luciano and Lansky establish a revitalized mob in New York City, effectively displacing their predecessors. Despite the gangsters' humble beginnings on the streets, they eventually rise to control much of the city.More Mobsters- #41 of 94 onThe 90+ Best Mafia Movies Of All Time
- #13 of 15 onUnderrated Historical Films That Got Overshadowed By Their More Successful 'Twin'
- #161 of 216 onThe 200 Best Crime Movies Ever
18Brad Pitt, Patrick Dempsey, Helen SlaterHappy Together is a 1989 American romantic comedy film starring Patrick Dempsey and Helen Slater. The film was marketed with the taglines, "Roommates by accident...lovers by choice", and "How do I love thee, Let me count the ways...". Brad Pitt, in one of his first roles, has a part in the film.
19Patrick Dempsey, Donald Sutherland, Mary Stuart MastersonHeaven Help Us is a 1985 comedy-drama film starring Andrew McCarthy, Mary Stuart Masterson, Kevin Dillon, Donald Sutherland, Wallace Shawn, Stephen Geoffreys, John Heard, and Patrick Dempsey.More Heaven Help Us- #86 of 96 onThe 90+ Best Movies Of 1985, Ranked
- #20 of 26 onThe Best Brat Pack Movies
- #105 of 157 onThe Best TriStar Pictures Movies List
20Patrick Dempsey, Beverly D'Angelo, Talia BalsamSonny Wisecarver (Patrick Dempsey) is a teenage Casanova. At the tender age of 15, he succeeds in seducing his older neighbor (Talia Balsam), and they run off to get married. The law catches up, the marriage is annulled, and soon Wisecaver has shacked up with another woman of advancing years (Beverly D'Angelo). When the newspapers get hold of the story, the young man hits the headlines with his very own nickname: "The Woo Woo Kid." This far-fetched comedy is based on a true story.
21Kevin Kline, Patrick Dempsey, Jesse EisenbergThe Emperor's Club is a 2002 American drama film directed by Michael Hoffman and stars Kevin Kline. It tells the story of a prep school teacher and his students at a fictional boys' prep school, St. Benedict's Academy, in Andover, Massachusetts. It was filmed at Emma Willard School in Troy, New York, although St. Benedict's Academy is said to be modeled after Phillips Academy, a preparatory school in Andover, Massachusetts.More The Emperor's Club- #43 of 51 onThe Best Movies Based on Short Stories
- #208 of 215 onThe Best Movies by Universal Studios
- #39 of 78 onThe Best Movies For And About Teachers, Ranked By Fans
22Patrick Dempsey, Colm Feore, Brigitte BakoThe Escape is a 1997 film directed by Stuart Gillard.
23Patrick Dempsey, Sherilyn Fenn, Edward HerrmannA Season in Purgatory is a 1996 crime fiction and drama film written by Robert W. Lenski and directed by David Greene.
24Michael Caine, Patrick Dempsey, Mia Sara20,000 Leagues Under the Sea is a 1997 television film produced by Village Roadshow Pictures, based on the novel Twenty Thousand Leagues Under the Sea by Jules Verne.
25Patrick Dempsey, Arye Gross, Daniel SternThree brothers -- Marvin (Daniel Stern), Bobby (Patrick Dempsey) and Buddy (Arye Gross) -- are asked by their father, Fred (Alan Arkin), to drive a 1954 Cadillac from Michigan to Florida in time for their mother's 50th birthday. The brothers haven't seen each other for years, and being cooped up in an old car for hours prompts endless squabbling. The topics range from choosing a radio station to serious grudges as the brothers try to survive the drive and maybe even bond in the process.
26Jonathan Silverman, Leah Lail, Ryan AlosioA single man's comment about monogamous relationships hits a sore spot with several couples at a dinner party.More Denial- #8 of 17 onUnderrated Movies About Historical Scandals
- #58 of 63 onThe 60+ Best Court & Law Drama Movies
- #7 of 36 onThe 30+ Best Jonathan Silverman Movies
27Patrick Dempsey, Claire Forlani, Robin TunneyJFK: Reckless Youth is a 1993 biographical film directed by Harry Winer.
28Patrick Dempsey, Jennifer Connelly, Sheila KelleyWhile on Christmas break, college student Michael (Patrick Dempsey) journeys to Quebec City to spend time with his attractive girlfriend, Gabriella (Jennifer Connelly). Not long after he arrives, Gabriella breaks up with him, but her two equally gorgeous sisters waste no time showing romantic interest. In the meantime, Michael is left to deal with Gabriella's eccentric grandmother (Lila Kedrova) and offbeat father (Andre Gregory), an academic who spends most of his time naked.
29Patrick Dempsey, Oliver Reed, Leonor VarelaJeremiah is a 1998 biographical, drama, history film written and directed by Harry Winer.
30Patrick Dempsey, Sally Kellerman, Al WaxmanMeatballs III: Summer Job is a 1986 film that was the third installment in the Meatballs film series, and the first in the series to be rated R. Unlike Meatballs Part II, this film follows Rudy, grown up and working on a summer job for an angry boss named Mean Gene. Unlike the first two movies, this one is not set at summer camp, but rather at a nearby marina.
