When I was 20 years old, a friend of mine told me he thought I looked like Sean Connery.

I was flattered, of course. Connery had just been named the “Sexiest Man Alive” by People magazine — at the age of 59, no less — and who wouldn’t want to be compared to that? Still, I didn’t really believe there was any resemblance, and I said as much. I mean… Connery was Connery, and I was just… well, me.

No, no, my friend insisted, he could definitely see it… something about my dark eyes, the arch of my brows, and the shape of my recently grown beard. Something about my attitude as well, he thought, my gruff intolerance for nonsense combined with a devil-may-care twinkle. I just chuckled at the absurdity of what he was saying. And the more talking points he came up with, the more embarrassed I felt, until I finally conceded his argument just so he would shut the hell up about it. I’ve never responded well to compliments, I’m afraid; I always have this nagging fear that the person giving them is somehow having a laugh at my gullibility.

That feeling is even more intense when the compliment is something I want to believe.

This was the spring of 1990, and Connery had recently become one of my cinematic heroes in almost perfect conjunction with him catching the second wind of his career. He’d won an Oscar three years earlier for The Untouchables, he’d been absolutely sublime as Indiana Jones’ dad the previous summer, and the day my friend made his comparison, The Hunt for Red October was playing to sell-out crowds in the biggest auditorium of the multiplex where I worked. (In fact, the Red October poster was hanging only a few feet from where my friend and I were standing that day, and I remember him nodding toward it as he made his case for the resemblance.)

The funny thing is, I wasn’t even very familiar with Connery’s work at that point. I knew who he was, of course. I’d seen a few of his films over the years besides the trio I just mentioned. But until that one-two-three punch — The Untouchables, Indiana Jones and the Last Crusade, and Red October — he hadn’t made a huge impression on me. Not even his James Bond films had struck a chord at that point in my life. I was as likely to think of him as the marshal from Peter Hyams’ High-Noon-in-space film Outland as anything. But starting in 1987, those three films caused something to click for me, and really, for everybody else who was going to movies around that time, making him one of the biggest stars of the moment. And I am not ashamed to admit I developed a bit of a crush on him. Strictly nonsexual, of course, much like George Costanza had for that rock-climber dude on Seinfeld. Like George’s rock-climber, Sean was an ideal I was fascinated by and aspired to. He was just… cool. And yes, having someone say that I reminded them of him, or vice versa, made me glow inside like a belt of  single malt.

You see, the spring of 1990 was a low point for me and my ego, something I’ve alluded to a few times recently on this blog. I wasn’t feeling especially cool or confident or sexy that day at the movie theater, or any other day of that difficult year. My friend had inadvertently told me exactly what I wanted — or perhaps needed — to hear. Which is probably why it embarrassed me so much, because I wanted to believe it was true. It wasn’t that I wanted to look like Connery so much as I wanted to be like him. To radiate masculinity and confidence as he did, to be absolutely, effortlessly comfortable in my own skin, as he always appeared to be.

That was the key of his appeal, I believe. Even now, after all these years of calling myself a fan and having seen many, many more of his movies than I had in 1990, I’m not certain if he was actually that fine of an actor, or if I just responded to… him. When you think about it, most of the great movie stars are essentially playing themselves, or at least some carefully curated version of themselves, and that was Connery’s true skill: being Sean Connery. When he turned up at the end of Robin Hood: Prince of Thieves, that ripple of excitement that zinged through the theater wasn’t because he so perfectly portrayed Richard the Lionhearted in only 30 seconds and a handful of lines; it was because people were excited to see the man himself. Who cared what the role was?

Of course, Connery’s hot streak of the late ’80s and early ’90s couldn’t last. Over the next decade or so, he made (in my opinion) only one really good film (The Russia House), a handful of mediocre ones (Medicine Man, Entrapment, The Rock, Finding Forrester) and two of the absolutely worst flicks I’ve ever seen: The Avengers (no relation to the Marvel film) and The League of Extraordinary Gentlemen. The latter was such a trainwreck, both in front of and behind the camera, that it killed Connery’s career. After that, he decided he’d had quite enough of making movies and retired. I’ve long felt sorry that his filmography ends on such a smoldering turd instead of one final triumph. Even a cameo in the much-derided fourth Indiana Jones film, all other things being equal, would’ve been a better note to go out on.

It’s been nearly 20 years since League, and in that time, he’s mostly stayed out of the spotlight. There have been occasional rumors that he wasn’t well, that he was suffering from dementia, and I always cringed at the thought of a man whose entire image was built on vitality fading away like that. His reputation has diminished somewhat as well in the wake of the #metoo movement, thanks to a couple interviews he gave in his younger days that keep bobbing to the surface like rotten apples, and because of claims made by his first wife in her autobiography. I don’t have much to say on that subject; I have no idea if Connery was a raging misogynist in his private life or if his remarks were just badly phrased and taken out of context. And honestly, it doesn’t matter very much to me. Because what he represents to me was never strictly about him anyhow.

That Red October poster now hangs in my office at home, the very same poster from the lobby of the multiplex where I used to work. It’s watched over me for 30 years now, as hard as that is to believe. I look at it every morning when I walk into that room to prepare for my day. I looked at it for a long time on Halloween, just over a month ago, the day that Sean Connery died at the age of 90. And as I looked, I found myself thinking of the roles he played that have mattered to me for one reason or another. Captain Ramius, of course, and Henry Jones Sr., and Malone, the Irish cop who teaches Elliot Ness how to get Capone. Juan Sanchez Villalobos Ramirez from Highlander became hugely important to me just a couple years after 1990. There was Marshal O’Neill in Outland and Edward Pierce in The Great Train Robbery, as nifty a heist film as you’re ever going to find. Hell, I even thought of Zed, the barechested, ponytailed, red-diapered “Exterminator” in John Boorman’s insane 1974 sci-fi epic Zardoz; Connery’s costume in that is all the proof of his self-assuredness you’ll ever need. And of course, there’s Bond. The role that made him, the role he spent years trying to live down. As it happens, I’ve rewatched the entire series over the past year, including the “unofficial” Bond he made in the ’80s, Never Say Never Again, and I can say unequivocally that, in my opinion, Connery was the best of them. His individual films weren’t necessarily the best of the series, but none of the other actors who’ve played 007 ever had a moment like the scene where we first meet him in Doctor No. That will forever be James Bond to me.

Of course, the day that Connery died, I also thought about that spring day in 1990. About how I felt so wounded then, and how I preened at the words of a friend that I only half believed. I’m far more comfortable with myself now than I was then, and I still don’t see much of a resemblance between myself and Connery. But every once in a while when I look at that Red October poster, I find myself still wanting to imagine that maybe… just maybe.

Rest in peace, you Scottish peacock.