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

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)

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 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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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.”

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)

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)

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)

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.

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.

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