Alright, Chacebookers, it’s Throwback Thursday, so I’m throwing it back to the 1980s. Long before he made millions of woman swoon every week as “McDreamy” on Grey’s Anatomy, Patrick Dempsey starred in three classic teen comedy films.

Well, classic to me, at least, as someone who grew up in the 1980s they made an impression on me.

The year was 1987, Dempsey was 21 years old (and married to a 47 year old woman, which could be the subject of a whole other post), and in August he starred in the film Can’t Buy Me Love.

Written by Michael Swerdlick and directed by Steve Rash, this film told the story of teenager Ronnie Miller (Dempsey), a nerdy kid who always longed to be part of the popular crowd. During his Senior year he pays a classmate named Cindy, one of the most popular girls in his high school who was suddenly in desperate need of $1000.00, to pretend to be his girlfriend for one month. He figures that that would be enough to make him popular. So they start fake dating, with Cindy giving him some fashion tips to update his hair and wardrobe. As he’s hanging out with Cindy and her friends, he’s neglecting his own real friends, who are all still nerds. As the month progresses, Cindy, who’d always ignored Ronnie before, starts to fall for him for real, despite having an older boyfriend who was away at college. When the month is up, Cindy reconsiders ending their arrangement, but Ronnie misreads her cues and instead stages a huge fake argument with her in the middle of the campus to “break up” up with her.  In the aftermath of his breakup, Ronnie becomes even more popular but also loses himself in the process. Becoming arrogant and self-centered. Then it all comes crashing down in spectacular fashion when Cindy gets fed up and reveals his secret to everyone.

This film stood out from the typical teen movies of the era. It managed to straddle the line between a feel-good John Hughes film and a raunchy sex comedy. Like a cross between Revenge Of The Nerds and Sixteen Candles. There was no nudity, sex was suggested but not shown, and I don’t recall much if any profanity. The chemistry between Dempsey and Amanda Peterson, who played Cindy, was great. Other standouts in the film were Seth Green in one of his earliest film roles, playing Ronnie’s bratty little brother Chuck, Darcy DeMoss as Cindy’s friend Patty, who also hooks up with Ronnie, Gerardo “Rico Suave” Mejia as Ricky, one of the popular boys, and Courtney Gains, as Ronnie’s best friend Kenneth, whom Ronnie neglects after he becomes popular. The message the film makes about being true to yourself is good, even if it’s presented a bit heavy-handed at times.

But, really, the entire film is worth watching just for the African Anteater Ritual scene.

Then a month later, Dempsey starred in In The Mood aka The Woo Woo Kid.

Written and directed by Phil Alden Robinson, this film was based on a true story. In 1944 a 14-year-old boy in California named Sonny Wisecarver had an affair with his next-door neighbor, a 21-year-old woman, who was in a common law marriage and had two children. Eventually, the two of them run off to Colorado and get married, but are arrested and brought back to California, where the marriage was annulled and the woman was sentenced to three years probation and the two of them were ordered to have no further contact with each other. His parents shipped Sonny to live with an uncle and aunt in another city where he meets and begins having an affair with a 25-year-old woman who was married, but whose husband was a soldier stationed overseas at the time. They also run off to another city but get caught and arrested. This second incident makes national headlines, the story of this teenager “lothario” captivating the public, and Soony gets nicknamed “The Woo Woo Kid” by the press. After a sensational trial, Sonny is sentenced to juvenile detention until he is 21, while the woman also gets three years probation. Sonny ends up escaping from the detention center, and finally meets a nice girl his own age.

Dempsey plays this role with such sincerity, you can’t help but root for him. Despite the salacious subject matter, Sonny comes off as an innocent kid who just really believes in love and is simply following his poor misguided heart. Talia Balsam and Beverly D’Angelo play the two older women, and they also come off pretty well although they really should have known better. Kim Meyers plays Wendy, the teenage girl he meets at the end, although it’s a really small role.

And then in 1989, Dempsey starred in Loverboy.

Written by Robin Schiff, Tom Ropelewski, and Leslie Dixon, and directed by Joan Micklin Silver, this is another film with salacious subject matter that nonetheless has a surprising amount of heart.

Dempsey stars as Randy, a teenager forced to work a job as a pizza delivery boy, while trying to raise money to go to college. He gets seduced by an older Italian woman named Alex (Barbara Carrera), who is one of his first customers. They come up with a code for when she calls the pizza place with an order that includes “extra anchovies” Randy knows that’s her summing him to her place for sex. After she has to move back to Italy, she’d spread the word about Randy to some of her friends, three unhappily married women, Kyoko (Kim Miyori), Joyce (Kirstie Alley), and Monica (Carrie Fisher). All the women call upon Randy using the same code.

Of course, hilarity ensues. There’s an ongoing subplot where Randy’s father finds a message to Randy from Alex and, assuming it’s a man, becomes convinced that Randy is gay (this was considered a funny thing in the 1980s). At one point, Randy gets a delivery order for extra anchovies but finds out it’s his from his mother, who doesn’t know that he’s the gigolos she’s hiring (he was recommended by Joyce, who is a friend of hers), and then the three women’s husbands find out what’s going on and team up to track Randy down and get their revenge.

Again, this could have easily been a raunchy sex comedy, but there’s no nudity, sex is implied, and there is a “moral” lesson to it. First, the joke is that Randy is initially inept when it comes to women, he’s the less likely candidate for a gigolo, but through his experiences with the women, he comes to learn how to properly treat them. And the women manage to come off as sympathetic as we clearly see how their husband’s have neglected them, leading to this point in their lives.

Dempsey starred in a film called Some Girls in 1988, which is notable because he showed full frontal nudity in it, but it doesn’t feel like part of this group of films, which is why I don’t include it in the “trilogy.” These three films in particular are familiar because they show Dempsey’s ability to play an essentially good character who makes you root for him even after he does bad things. And his charm is undeniable, he’s a skinny gangly kid, not someone you’d picture as a sex symbol. In fact, it’s still hard for me to see him as a sex symbol now, I just see that goofy nerdy kid from the 80s when I look at him. But obviously millions of women (and gay men) see differently.