1985
This is from a movie called Heaven Help Us, about Catholic school boys, and yes, that is both Andrew McCarthy and Kevin Dillon over Patrick's shoulders. The other two weren't named. Sorry, other two. We are seeing some VERY early Judgmental McDreamy energy here, as well as the clear indicators of a robust coif.
1987
THIS is something called "In The Mood," previously named "The Woo Woo Kid," which is based on the VERY CREEPY true story of a 14-year old who runs off with his 21-year old neighbor to get married, gets busted, goes before a judge, gets sent off to live with his aunt, and then eventually does the exact same thing again?!? I guess they're in a manhole because they're... hiding?
1987
And this is of course "Can't Buy Me Love," in which Patrick attempts to -- wait for it -- buy love. Okay not really. He pays a popular girl a grand to be his girlfriend and make him into a cool kid, and guess what, turns out he was cool all along. His hair can BARELY be suppressed here. It wants to spring. It wants to LIVE. And live it will.
See? In the grand tradition of these movies, he just loses the classes and buys some gel and ditches the cap and BOOM. He's a legend.
1988
THIS is from a movie called "Some Girls," and IMDb would like you to know this: "Michael flies up to French Canada to visit his girlfriend and her wacky family. She doesn't love him anymore, the grandma mistakes him for her late husband, the sister appears naked and makes advances, the dad likes to be naked as well." OKAY THEN. The curl and texture of Dempsey's hair varies enough that sincerely feel like someone crimped this and then backcombed it a bit, to turn it from the previous slide into this.
1988
And then it ended up HERE. LOOK AT THIS. It's so floofy. So kissed by California.
1989: Loverboy
Frosted. Tips. Actually this entire visual is hilarious.
1989
I haven't seen Loverboy, but I guess there is room in that movie for both Frosted Tips With Two Belts, and Dark Hair With No Pants.
1989
This is here solely to honor Barbara Carrera's hat.
1990
This is from "Coup de Ville." And in addition to the mop of hair, the forearms are in full force.
1991: Mobster Wrap Party
Here's a story I didn't know: That is his manager, Rocky Parker, and she and Dempsey got MARRIED when he was 21 and she was 48. He claims he became best friends with her son AFTER the marriage, rather than marrying his best friend's mom, but regardless: They stayed married for seven years. That's got to be more years than people expected.
1991: Mobsters
Here is P. Demps in the movie they were celebrating, with his most restrained coif yet. I miss the hair. Luckily, we're about to get so much more of it.
1994
He was in "With Honors" this year, which is the movie where Brendan Fraser needs to graduate and Homeless Joe Pesci holds his paper hostage somehow, and.... I suspect everyone learns a lot of valuable lessons about life? This IS a total Emo College Bro look. It might also be his Divorcing Bad Boy mood.
1994
This is not a good look on him. He looks like he would've been in the 90210 episode where Brenda leaves home and moves in with a bunch of stand-up comics who are lying to her that she's funny (I might be editorializing about that last part). It's a VERY creepy aura that feels like a dude who'd be like, "You're super mature for your age, Brenda."
1995
AND LO, IT CONTINUES.
1995
AND ON AND ON. This Dempsey probably does slam poetry in his college town for too long after he graduated from there.
I don't have a date for this photo. But it is McDreamy, McSteamy, and McEEEEEEEEEmy. Whew.
1998
I forgot that he turned up on Will & Grace. Here he is, in a turtleneck, turning up on Will & Grace. As we'll soon be reminded, Dempsey looks quite good in a turtleneck.
I don't know what this was from; the caption simply said, "Headline." His hair is showing shades of the potential we are about to see displayed...
... in Sweet Home Alabama, where he played a really frankly rather GREAT love interest for Reese Witherspoon, whom she spurns for her first love Josh Lucas (if you are a person in the world who has experienced fiction, this is not a spoiler; it's obvious where this one is heading). If I recall correctly, he is VERY nice to her and makes it FAR too easy on her to bail on him at the literal last second, and frankly I would have picked him. I don't care how good Josh Lucas is at blowing glass. Not a euphemism, although I guess it could be.
BEHOLD. It is standing at FULL ATTENTION. Reese, how do you give up your chance to run your fingers through THAT every day?
Yes, Patrick, I WILL drink to you and that rogue forelock flopping onto your forehead.
2005
And, enter Dr. Derek Shepherd. I'm in season eight now of my rewatch, and he's getting a bit self-righteous. But early on... dang, in season one, the way he looks at Meredith... so good. SO GOOD. This show's early seasons really hold up, much as his hair does.
And he knows it. HE KNOWS.
2006
I like a little curl in the mix.
2007
Are we getting the merest touch of silver fox here?
2007
Enchanted was a very cute movie, and this is A LOT of great hair in one shot.
2007
I am worried he was rained on here, or something. Perhaps he ate some bad shrimp and couldn't pomade the poof to its standard height. Again, not a euphemism, but... again, honestly also could be.
2007
He made up for it on this night. He was like, "WE WILL NOT LIE FLAT AGAIN."
2008
Now that we have seen many, many shots of Patrick Dempsey's face, we can all appreciate that this is most definitely not an accurate depiction of Patrick Dempsey's face. WHY ARE YOU DOING THIS TO PATRICK DEMPSEY'S PLEASING ACTUAL FACE?
2011
WAIT A MOMENT. Is it the lighting, or does he have one frosty blond streak?!?
2013
And now, the hints of steel arrive.
2016
I totally forgot he was in Bridget Jones's Baby, a movie I watched with half an eye -- it's fine! -- and so I don't TOTALLY remember, but I think he played yet another amiable and great love interest who was part of a triangle where both choices make sense.
2019
Someday, Patrick Dempsey will write a memoir, and I hope it will have an entire chapter about Olivia Culpo's outfit here. He and I are having a very, very lengthy silent conversation here.
2019
And here, he's in Cannes, looking for all the world like a wealthy European businessman who is welcoming the auctioneer at an exclusive Sotheby's event. I'm here for that, frankly. Happy Birthday, Dempsey! Thank you for the headsuit.