7 Patrick Dempsey Movies & TV Shows, Ranked

Can’t Buy Me Love is one of the earliest breakout parts for Patrick Dempsey. It’s certainly one of the first times he plays a romantic lead in his career. This movie is also so unabashedly and painfully representative of the ‘80s. The fashion and music from the film are the better sides of that coin. The premise itself is the less-than-favorable side, in that it’s not entirely romantic that Dempsey’s Ronald buys the affections of Cindy (Amanda Peterson). 

Even though the movie tries to convey that popularity and love can’t be bought, it doesn’t really land with great effect, and Ronald becomes rather unlikable along the way. Besides, Dempsey was only getting started as a leading man, and those reasons are enough to land this movie at the bottom of this list. Can’t Buy Me Love may also be a frustrating watch for rom-com fans who find similar themes better explored in Cameron Crowe’s Say Anything (1989). Furthermore, if you’re looking for another take on Can’t Buy Me Love’s lawnmower ending, I suggest Emma Stone and Penn Badgley’s homage in Easy A (2010).

Scream 3 is notoriously one of the lower-rated movies in the Scream (1996) franchise, and rightfully so, in some ways. I wasn’t all that impressed by the Ghostface reveal because it felt like it was trying to hold onto threads to the original movie that just weren’t there. When I marathoned the movies a few years back, I was shocked to learn that Patrick Dempsey was in the movie as Detective Mark Kincaid, let alone that his character was the love interest of final girl Sidney Prescott (Neve Campbell). Until then, the best romance in the franchise was that between Gale Weathers (Courtney Cox) and Dewey Riley (David Arquette).

Campbell and Dempsey’s chemistry really worked. Their characters found a common ground in the scary things they’d encountered in their lives. It was a great romantic subplot that I didn’t really expect, a lot like that in Happy Death Day (2017). All of which makes it more disappointing to know that Sidney is married to a different Mark later in the franchise. Regardless, Scream 3 may not be the best Scream movie, but it is for horror fans who like a bit of romance in the mix. It’s also where Dempsey’s well-known charm starts to take shape ahead of his more leading roles.

Sweet Home Alabama is the first movie I think of when someone mentions Patrick Dempsey and romantic comedy in the same sentence. Despite his extravagant proposal, Dempsey’s Andrew never had a real shot with Melanie (Reese Witherspoon). The chemistry is too strong with Melanie and her ex, Jake (Josh Lucas), with whom she never finalized her divorce. 

Despite Melanie’s family partaking in a Civil War reenactment (along with a few things painfully representative of the early 2000s), this movie is tooth-achingly sweet. When Melanie asks him why he wants to marry her, Jake says, “So I can kiss you any time I want,” and it still makes me blush. Sweet Home Alabama may not be a win for Dempsey’s character, but it certainly is for fans of small-town rom-coms, like The Proposal (2009).

In Ferrari, Patrick Dempsey plays the Italian racing driver, Piero Taruffi, down to the bleached hair. His role may not be the main focus of this movie, which offers a different take on Ferrari than the team-focused Ford vs. Ferrari (2019). Ferrari spends more time with the Ferrari family, namely Adam Driver as Enzo and Penélope Cruz as Laura. Nevertheless, Dempsey leaves an impression as the Ferrari driver who raced in and won the Mille Miglia. 

As a fan of Dempsey, I know that he’s been racing cars for a couple of decades and owns Dempsey Racing. As a fan of motorsports, I often see Dempsey on TV at tracks ahead of races. So, it’s exciting to see him play such a figure on the big screen. In that sense, this movie is a part of a larger boom that appeals to motorsports fans, like F1 (2025).

Patrick Dempsey’s role in Dexter (2006) prequel series, Dexter: Original Sin, is almost as short-lived as the show. The main difference is that Dempsey’s character’s arc has a beginning, middle, and end, but the show ends abruptly—with a cancellation after a renewal. Dempsey uses his memorable charm to disguise himself around Dexter Morgan (Patrick Gibson). Then again, Dempsey’s Captain Aaron Spencer being unmasked as the Masked Kidnapper isn’t that much of a twist.

The character’s stance in law enforcement, closeness to Harry Morgan, and his mentorship of Dexter add up to something more than on paper. Dexter: Original Sin follows that through with Aaron becoming Dexter’s fourth (of many) victims. While pivotal to the lore of the titular character, the show’s cancellation makes it difficult to invest in retroactively for casual viewers of the Dexter franchise or otherwise. If you’re interested to see Dempsey in more horror, Thanksgiving (2023) has the benefit of being a standalone movie.

Before Grey’s Anatomy (2005), Enchanted is where I met Patrick Dempsey. Now, I see the appeal of James Marsden’s Prince Edward in a way that I didn’t when I was younger. Then, I was so charmed by Dempsey’s Richard and his romance with Gisele (Amy Adams). Their relationship was so cute—and it still holds up. This movie is for fans of musicals (“That’s How You Know” is still iconic!) and rom-coms where a cynic falls or an optimist. 

For the latter, Enchanted pairs nicely with the feel-good Confessions of a Shopaholic (2009). I’m not sure that the sequel, Disenchanted (2022), lives up to the original in any way, which is deeply unfortunate. Then again, it’s almost unfair to saddle the sequel with the task of trying to recapture that magic. It’s lightning in a bottle with a fresh take on familiar tales.

Patrick Dempsey’s career is far from over, but, from where it stands now, there isn’t a more iconic character in his filmography than Dr. Derek Shepherd. It’s probably his most memorable role. For an impressive and increasingly rare 11 seasons, Dempsey played the neurosurgeon on Grey’s Anatomy. He’s the reason why the saying “It’s a beautiful day to save lives” and ferry boats make me sad now. Derek Shepherd is also the McDreamy to Dr. Mark Sloan’s (Eric Dane) McSteamy. One of the defining parts of that tenure is Derek’s romance with Meredith Grey (Ellen Pompeo). Sadly, that relationship ends with heartbreak, changing the show’s trajectory. 

But, after exiting in 2015, Dempsey reprised his role opposite Pompeo in 2020. Their characters reconnect on a beach in Meredith’s dream sequence while she was in a coma from COVID. It was beyond emotional seeing these two characters together again. These are features other medical dramas just can’t replicate because of the time that Dempsey spent as this character. 

If you’re looking for a medical drama with a long-term investment, Grey’s Anatomy is it. It just got renewed for Season 23! If you’re looking to get to know other characters who are important to Derek, including his ex-wife, Addison, and younger sister, Amelia, you may want to check out the underrated spinoff series, Private Practice (2007).