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The Movies and TV Shows That Prove Patrick Dempsey Has Always Been Dreamy

From 'Loverboy' to 'Grey's Anatomy' he's only gotten better with time!

When you watch Patrick Dempsey movies or TV shows, you wouldn’t guess this boyishly handsome star has been in show biz for over 35 years. From touring in small stage productions to feature films to mega-television success to commercials to being the runner up on People‘s Sexiest Men Alive list twice, Dempsey’s charm and charisma have won over millions of viewers. 

Dempsey, now 57, seems to only get better with age, going from a cute teenager to a full-on dreamboat to a silver fox. Here, we take a trip down memory lane with our favorite Patrick Dempsey movies and TV shows, from his first foray into acting to his latest film, Ferrari

How Patrick Dempsey became an actor

Growing up in small-town Maine Dempsey achieved early fame as a juggler. That’s right. In his youth, Dempsey won second place at the International Jugglers Association Championship. “I started off as a juggler,” Dempsey said in a BBC interview. “I used to do a half-hour show on the weekends to make money as a kid. Then I went to Cleveland, Ohio in 1983 to the juggler’s competition and came in second.  So that was my first job in front of people, being a juggler.” 

An invitation to audition for a role in the stage production of Torch Song Trilogy kickstarted Dempsey’s acting career. After a successful audition, he spent the following four months touring with the company in Philadelphia. Dempsey took a liking to touring and followed up the play with a lead role in Brighton Beach Memoirs

Patrick Dempsey movies and TV shows

Shortly after making a splash on the stage, a young Dempsey moved to the screen. He started out with small, uncredited appearances in the mid ’80s, and joined the cast of Fast Times, a short-lived sitcom adaptation of the classic teen movie Fast Times at Ridgemont High, in 1986. The next year, at age 21, he began taking on bigger and better roles. Here are some of the most notable Patrick Dempsey movies and TV shows.

In The Mood (1987)

Patrick Dempsey in In the Mood
Patrick Dempsey and Beverly D’Angelo in In the Motion Pictures

Dempsey co-starred with Beverly D’Angelo in In the Mood, his first big movie part. Based on a true story, the film follows 14 year-old Sonny Wisecarver as he woos two older women. The film was quite controversial as it coupled an older married woman with a much younger man. Coincidentally, Dempsey’s first marriage was to his manager and acting coach Rochelle “Rocky” Parker when he was 21 and she 48. 

Meatballs III: Summer Job (1987)

Dempsey with Sally Kellerman Meatballs III
Patrick Dempsey with Sally Kellerman in Meatballs III: Summer Productions, Inc. Cinepix

Dempsey acted in the raunchy comedy Meatballs III: Summer Job alongside Sally Kellerman of M*A*S*H fame the same year. The film follows a porn star (Kellerman), who died on the job as she tries to impress a nerd working at a summer resort (Dempsey) by helping him pick up girls, all in the hopes of getting into heaven.

Can’t Buy Me Love (1987)

American actor Patrick Dempsey, London, (Patrick Dempsey movies and TV shows)
Patrick Dempsey in 1988, the year after he starred in Can’t Buy Me LoveMichael Putland/Getty

Can’t Buy Me Love was when Dempsey’s movie career really kicked off. He played a nerdy teen boy, who gives a popular cheerleader $1,000 to pretend to be his girlfriend. The film made Dempsey into a teen magazine staple.

Loverboy (1989)

Lover Boy cast
Patrick Dempsey starred alongside Kirste Alley, Kim Miyori and Carrie Fisher in Pictures

Dempsey starred in Loverboy alongside Hollywood biggies like the late Kirstie Alley and Carrie Fisher. He played a handsome college student looking to make extra money by delivering pizzas and — shall we say — other services.

Mobsters (1991)

Christian Slater, Patrick Dempsey, Costas Mandylor and Richard Grieco on set of the film 'Mobsters', (Patrick Dempsey movies and TV shows)
Christian Slater, Patrick Dempsey, Costas Mandylor and Richard Grieco in MobstersMetro-Goldwyn-Mayer/Getty

Dempsey moved into more serious territory with the role of gangster Meyer Lansky, in Mobsters, the story of a group of young criminals in New York City. Christian Slater, Richard Grieco, and Costas Mandylor also starred. The movie received negative reviews and flopped at the box office.

JFK: Reckless Youth (1993)

(Patrick Dempsey movies and TV shows) Patrick Dempsey smiles side by side
Left: 1995; Right: 1994Frank Trapper / Contributor/Getty;Kravitz/FilmMagic/Getty

In 1993 Dempsey played a young John F. Kennedy in JFK: Reckless Youth, a TV miniseries that follows Kennedy’s life before the presidency based on a 1992 biography of the same name.

Season in Purgatory (1996)

Season in Purgatory cast
The cast of A Season in Purgatory (clockwise from left: Sherilyn Fenn, Craig Sheffer, Wendy Phillips, Patrick Dempsey and Brian Dennehy)

Dempsey dabbled more in TV with a Season in Purgatory, a miniseries in which he played a writer who discovers a deadly secret which could destroy a rising politician (Craig Sheffer) and his rich and powerful family.

Crime and Punishment (1998)

Julie Delpy as Sonia and Patrick Dempsey as Rodya in "Crime And Punishment." (Patrick Dempsey movies and TV shows)
Julie Delpy and Patrick Dempsey in Crime and PunishmentHulton Archive/Getty

Crime and Punishment, the TV movie based on Fyodor Dostoevsky’s novel, saw Dempsey in a leading role as Rodion Raskolnikov. He started alongside Sir Ben Kingsley, Julie Delpy and Eddie Marsan.

Will & Grace (2000-2001)

Patrick Dempsey side by side (Patrick Dempsey movies and TV shows)
Dempsey appeared on Will and Grace in 2001Stephen Shugerman / Stringer/Getty; Frederick M. Brown / Stringer/Getty

Dempsey’s first major television role was a three-episode arc as Will Truman’s closeted sportscaster boyfriend on the ultra popular sitcom Will & Grace from 2000 to 2001. 

Scream 3 (2000)

Scream 3
Patrick Dempsey in Scream

Dempsey played a detective in the third installment of this popular horror series. His character was supposed to return in Scream 4, but Dempsey turned it down.

Sweet Home Alabama (2002)

Sweet Home Alabama
Reese Witherspoon and Patrick Dempsey in Sweet Home Pictures

Dempsey had a high-profile role as Reese Witherspoon’s fiancé, Andrew, in the rom-com hit Sweet Home Alabama. (Read more about Reese Witherspoon movies and TV shows here!)

Enchanted (2007)

Patrick Dempsey and Amy Adams during Patrick Dempsey, Amy Adams and Jeff Watson on the Set of Disney's "Enchanted" - July 10, 2006 at Central Park in New York City, New York, United States.Patrick Dempsey movies and TV shows)
Patrick Dempsey and Amy Adams in EnchantedJason Kempin/FilmMagic/Getty

In 2007, Dempsey starred in the Disney film Enchanted as a real-life Disney prince. Opposite Amy Adams, the suave actor captured our hearts with ease. 

Grey’s Anatomy (2005-2021)

Patrick Dempsey on Grey's Anatomy
Patrick Dempsey in Grey’s

When Dempsey took on the role of the handsome Dr. Derek Shepherd, Meredith Grey’s (Ellen Pompeo) love interest, he instantly garnered public attention, becoming known as Dr. “McDreamy.”

He’s the ideal man, and that’s what [series creator Shonda Rhimes] constructed,” Dempsey said of his signature character in a 2021 Hollywood Reporter interview. “There’s a projection [of him] onto me when you come in contact with fans, certainly with the younger and older fans. There is a certain amount of expectation. There is a responsibility to it. It made me grow, too. There were good qualities [of his] that you work on to obtain.”

Ellen Pompeo and Patrick Dempsey (Patrick Dempsey movies and TV shows)
2007/2021Jon Kopaloff / Contributor/Getty; Ellen Pompeo’s Instagram

The Grey/Shepherd onscreen relationship was the central focus of the show and viewers eagerly tuned in to watch them. Dempsey appeared in the main role in episodes from 2005 through 2015 and then in 2020, he appeared as Derek Shepherd at the start of the series’ 17th season for the first time since his character had died in 2015. Fans are still mourning the loss of his character all these years later.     

Bridget Jones’ Baby (2016)

 (L-R) Patrick Dempsey, Renee Zellweger and Colin Firth attend the Bridget Jones' Baby photocall at Villamagna Hotel on September 9, 2016 in Madrid, Spain. (Patrick Dempsey movies and TV shows)
Bridget Jones’ Baby stars Patrick Dempsey, Renée Zellweger and Colin Firth Pablo Cuadra/Getty

Dempsey has proven there’s life after McDreamy. Following his onscreen “death,” he starred in Bridget Jones’ Baby, the third film in the popular rom-com franchise, alongside Renée Zellweger and Colin Firth.

Disenchanted (2022)

Amy Adams (L) and Patrick Dempsey are seen filming "Disenchanted" in the Upper West Side on April 05, 2022 in New York City. (Patrick Dempsey movies and TV shows)
Amy Adams and Dempsey in DisenchantedGotham/GC Images/Getty

In 2022, Dempsey starred in the Enchanted sequel, Disenchanted, along with Amy Adams, James Marsden, Idina Menzel and Maya Rudolph. The film wasn’t as popular as the original, but it was fun to see Dempsey reprise his charming role.

Ferrari (2023)

Adam Driver and Patrick Dempsey attend a red carpet for the movie "Ferrari", 2023  (Patrick Dempsey movies and TV shows)
Adam Driver and Patrick Dempsey attend a red carpet event for Ferrari Maria Moratti / Contributor/Getty

Dempsey’s newest blockbuster film Ferrari follows an automotive, mogul Enzo Ferrari (Adam Driver), whose family redefined the idea of the high-powered Italian sports car and practically came up the concept of Formula One racing.

In addition to being an actor, Dempsey is also an auto racer, so the Ferrari role is a perfect fit. The film will be released on December 23, 2023.

Patrick Dempsey’s personal life

Offscreen, Dempsey has a passion for philanthropy. In response to his mother’s numerous bouts with cancer, he helped start the Dempsey Center at Central Maine Medical Center in Lewiston. In 2017, Dempsey received an honorary doctorate from Bates College in Lewiston for his philanthropy in the town and funding of The Dempsey Center, just blocks from the Bates campus. 

Patrick Dempseys Family (Patrick Dempsey movies and TV shows)
Dempsey with his wife, Jillian, and their children in 2016Dave J Hogan / Contributor/Getty

When Patrick Dempsey isn’t starring in movies and TV shows, he takes pride as a family man to his wife, Jillian, and their three children. Jillian is a hair and makeup artist, and the couple met in 1994 when Patrick became a client at her hair salon. They married in 1999, and despite a near-spilt in 2015 these two have been together ever since.

Patrick and Jillian Dempsey side by side (Patrick Dempsey movies and TV shows)
Left: Jillian and Patrick Dempsey in 2001; Right: The couple in 2023Gregg DeGuire / Contributor/Getty; Stefania D’Alessandro / Contributor/Getty

For more of our favorite actors, click through the links below!

George Clooney Young: 19 Must-See Photos of the Heartthrob Over the Years

Robert Redford Young: 20 Rare Photos of The Handsome Icon Who Stole Our Hearts

Hilarious, Handsome & Talented: 15 Chris Pratt Movies We Can’t Get Enough Of

Mark Harmon Young: A Look Back at How the Handsome ‘NCIS’ Star Got His Start

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