Patrick Dempsey's most memorable movie and TV roles

An appreciation of the actor's body of work in celebration of his sexy new title.

As Grey's Anatomy fans have known since the pilot, Patrick Dempsey is one hot doc. And now he is officially the Sexiest Man Alive, as awarded annually by PEOPLE. But Dempsey's talent doesn't only reside in that gorgeous head of hair.

To celebrate the actor's official induction into the sexy pantheon alongside the likes of Chris Evans, Paul Rudd, and Michael B. Jordan, EW has rounded up some of his best — and hottest — roles, from a nerd with a heart of gold to Bridget Jones' possible baby daddy.

Dempsey can next be seen alongside Adam Driver in the Michael Mann-directed biopic Ferrari (opening Christmas Day) playing Italian Formula One driver Piero Taruffi. To tide us over until then, here's a look back at some of his best movie and TV roles.

Can't Buy Me Love (1987)

One of Dempsey's earliest breakout roles came in this sweet teen comedy. The actor plays Ronald, a nerd with a heart of gold, who pays a cheerleader (Amanda Peterson) to pretend to date him to boost his social status. Dempsey brings the perfect balance of awkwardness and genuine romanticism to his scenes with Peterson, and forges a believable arc from meekness to self-confidence for Ronald. Though his quiet wallflower character is a far cry from the roles he'd play in his later career, it still shows his ability to channel romantic energy and charm to a movie that desperately needs it. —Wesley Stenzel

Loverboy (1989)

Well, using anchovies to hook up might seem weird, but this was the '80s after all. Dempsey stars as Randy, a boyishly handsome pizza delivery guy who suddenly finds himself needing to pay for his college tuition or have to drop out. After a delivery leads to a tryst with a wealthy but married woman, she refers her friends to him and he starts a new business delivering a side order of Randy-lovin' to rich, lonely women who have one request with their pizza orders: extra anchovies. But he soon learns gigolo life ain't the piece of pie that it seems. Though the film is full of problematic tropes of the era, Dempsey's boyish charm will have you dialing for pizza ASAP. —Yolanda Machado

With Honors (1994)

The actor takes on a supporting role as Everett Calloway next to Oscar winner Joe Pesci and future Best Actor Brendan Fraser, to play the womanizing radio DJ roommate of Fraser's Monty Kessler. After Monty's thesis is held hostage by a homeless man named Simon (Pesci), the roommates agree to live with him in order to get one page of Monty's thesis back per day. Together, they bond with Simon, and learn hard lessons in life and love — all set to Madonna's unforgettable ballad, "I'll Remember." —Yolanda Machado

Scream 3 (2000)

In the third installment of Wes Craven's self-aware slasher-comedy series Scream, Dempsey portrays Mark Kincaid, a detective investigating the Ghostface murders during the production of Stab 3 in Hollywood. Though it's not a main role, Dempsey uses his screen time wisely to do what all great Scream supporting actors should do: act just suspicious enough to make the audience continually question whether or not he could be the masked killer himself. He also maintains the right amount of on-screen professionalism and respectability that if he's not the killer, you hope that he'll live to see the end of the movie. —Wesley Stenzel

Will & Grace (2000-2001)

Before Dempsey stole Meredith Grey's heart, he won over Will Truman's during a three-episode, season 3 arc of Will & Grace as Matt Moshea. They first meet when Will (Eric McCormack) — hiding in a dressing room equipped with a headset — tries to help Jack (Sean Hayes) flirt with the smart and sophisticated Matt. But it quickly becomes evident that Will and Matt should be the ones talking — until Will gets scared away when he finds out Matt is a sports reporter. Eventually working up the nerve to ask him out, they start dating and things are going well until Matt, still closeted, asks Will to keep their relationship a secret, even referring to Will as his brother in front of his boss. Game over. —Gerrad Hall

Sweet Home Alabama (2002)

As the other man standing between Reese Witherspoon's Melanie, a successful New York fashion designer who has long buried her Southern roots, and her childhood sweetheart Jake (Josh Lucas) in rom-com Sweet Home Alabama, Dempsey's wealthy Andrew should, by all accounts, be easy to cast off. But McDreamy brings a softness to the role. Despite Melanie concealing her background and the fact that she's still married to her childhood beau, Andrew loves her for her and commits to forever — and even bows out gracefully when she leaves him at the altar. (His overbearing mother, however, gets a punchin' square in the jaw.) —Jessica Wang

Grey's Anatomy (2005–2015, 2020-2021)

As the smoldering Dr. Derek Shepherd on Grey's Anatomy, Dempsey earned his "McDreamy" nickname from his very first encounter with Meredith Grey (Ellen Pompeo), a one-night stand that evolved into one of television's greatest love stories. The role earned Dempsey two Screen Actors Guild Awards, two Golden Globe nominations, and cemented his status as a swoon-worthy romantic lead. His show departure in 2015 after 11 seasons left fans — and Meredith — heartbroken. But despite being killed off in a car crash, Dempsey shockingly returned for several episodes in season 17, appearing in a dream sequence on a beach as a comatose Meredith fought COVID-19. Her literal dream man and ours. —Jillian Sederholm

Enchanted (2007) and Disenchanted (2022)

In Enchanted, Disney's 2007 musical rom-com tribute to its classic princess films, Dempsey plays Robert, a no-nonsense single dad who gets swept into a fairy tale romance with Giselle (Amy Adams). Dempsey's realism and cynicism in the role makes him a perfect foil for Adams' bubbly cartoon princess brought to life, and his sweetness toward his on-screen daughter (Rachel Covey) reveals an emotional depth below his hardened exterior. His jaded everyman performance is deceptively complex in all his scenes with Adams, as he's equally baffled and enamored with her unshakable effervescence and childlike optimism. In the 2022 sequel, Disenchanted, he gets to enter a totally different mode, as Robert falls victim to a spell that makes him believe he's a medieval knight, effectively letting Dempsey channel James Marsden's noble himbo performance from the original movie. —Wesley Stenzel

Made of Honor (2008)

In rom-com Made of Honor, Dempsey turns on the charm as commitment-phobe Tom, a serial dater who doesn't realize that the love of his life has been there all along in the form of Hannah (Michelle Monaghan), his best friend since college. Tom realizes his feelings for Hannah while she's away in Scotland for work and is determined to tell her once she returns — only she does so with a dashing fiancé, Colin (fellow Grey's Anatomy star Kevin McKidd), in tow. When Hannah asks Tom to be her maid of honor, he agrees with the intent to win her heart in this modern-day fairytale complete with Scottish castles. —Jessica Wang

Bridget Jones Baby (2016)

Joining the final movie in the beloved trilogy, Bridget Jones' Baby, Dempsey's Jack Qwant, an American billionaire entrepreneur, takes on Mr. Mark Darcy himself (Colin Firth) to win the love of heroine and audience favorite Bridget Jones (Renee Zellweger). After a tryst at a music festival campground following a breakup, Bridget has no idea who may be the father of her unborn baby. But both prospective papas are all in — for the baby and for Jones. Entering a well-established rom-com franchise already three books and two films deep is a hard feat for anyone, but Dempsey supplies the charm that makes the big Mamma Mia "who's the daddy" theme a true delight.—Yolanda Machado

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