Welcome to Top 5 Fun Friday, a regularly-occurring blog feature where I give you a list of extremely specific pointless shit from my life no one asked for. Why? Because the internet is incredibly un-fun in 2020 and I miss blogging. It’s Friday and these will be fun! This week’s list…

Top 5 Movie Characters Much Older Than I Am That I’ve Been Attracted To

Comedian Neal Brennan has a great bit about what it’s like to sleep with women in their late 30s or early 40s. He argues they know their bodies too well to the point that as a dude, it’s like we’re working for you.

“Alright, young man, hop on in there real quick. Why don’t you start me with 15 or 16 good pumps and let me see what I’m dealing with. That’s fine. Look, I’m gonna put your right hand on my left breast. Young man, go ahead and kiss my neck. Aaaaand, kiss it again. Pull my hair. (a pause) I just came twice, get the fuck out of my house.”

Efficient! And fucking hilarious.

Now then, onto this week’s Top 5 Fun Friday topic. I couldn’t have possibly had any practical knowledge of what Neal Brennan exposited in this brilliant standup bit, but I suspect one of the reasons it made me laugh so hard is that my favorite way of consuming movies is happening upon them while channel surfing. The streaming age has made this practice exponentially more annoying, which is turning me crusty faster than I’d like.

And as I’m channel surfing through old movies, I started thinking about how many times I’ve been smitten with a woman not just a bit older than me like when I crushed hard on Gabrielle Union in Bring It On (I was 19 when this movie came out, she was 28 but playing an 18 year-old). No, I’m talking at least a generational difference, possibly two, and in one case, even more than that. Why this happened to me I’ll never know, and I certainly don’t care enough about the reasons to psychoanalyze myself. I’d rather just recall some gorgeous women that were way out of my league.

So, let’s start with the smallest age distance between me and my celebrity crushes and go from there.

Jennifer Coolidge as Stiffler’s Mom in American Pie

Her age at time of movie’s release: 38. Mine: 17. Difference: 21 years.

I’m a 39 year-old man. American Pie was released the summer between my junior and senior year of high school. Any list of this sort that doesn’t include Stiffler’s Mom is a list not worthy of the absolutely miniscule amount of bandwidth it takes up on the internet. What’s remarkable in thinking about Jennifer Coolidge’s turn as Stiffler’s Mom is that the first time you see her in the flesh (which means I’m ignoring John Cho and that other guy shouting “MILF!” at her picture during that early party scene), she’s standing there smoldering and intimidating and just even more impossibly gorgeous than she’d been built up throughout the movie.

And look, I knew even then that if I were in Finch’s shoes in this movie that I’d have no prayer of seducing her, let alone of even not boring her to tears with my bland, dorky high school ass. Just like any other high school dweeb, I was thoroughly overmatched. But, and as sad as this is to remember, I think as desperately horny teenagers, we all shared a couple of far-fetched and totally irrational fantasies. The first is that when the opportunity presented itself, we’d be magically great at sex. The second is that some intrepid cougar would take us under her wing and be hopelessly charmed by us and want to show us the sexual ropes.

Stiffler’s Mom represents both of those fantasies together as Finch at the age of 17 is somehow able to manufacture urbane cocktail party banter about 15^th century Italian painters, drink scotch neat without coughing or throwing up, and then giving it to this fantasy-come-to-life with the skill of a legendary swordsman. After writing this, it’s entirely possible this fantasy isn’t actually about Stiffler’s Mom, but instead about watching Finch get the opportunity of a lifetime, and then improbably knock it out of the park. Weird. Although that’s not to in any way denigrate just how fucking hot Jennifer Coolidge is in this movie.

Jamie Lee Curtis as Helen Tasker in True Lies

Her age at time of movie’s release: 36. Mine: 13. Difference: 23 years.

While I still enjoy True Lies in many ways, let’s say I have more than a few problems with its gender politics and troubling implications about race. I can’t help but feel incredibly icky thinking about how psychologically fucked up it is that a husband would trick his wife into believing that she has to pretend to be a hooker and put on a deviant peep show for some arms dealing creep in order for her to avoid the destruction of her life, her family, and basically her entire world. Gross.

I certainly wasn’t thinking that at 13, though. What I was thinking about is how Jamie Lee Curtis looked like straight fire in that striptease scene, a trick made even more noteworthy considering several elements of the scene are played for comedy. She absolutely nails both the comedic and sensual beats in a scene that left me transfixed for the entirety of its duration. Which was both a blessing and a curse because it allowed me to forget for the briefest of moments that I was sitting next to my mom the entire time. I can say with the utmost certainty that there’s nothing worse than getting all horned up and then remembering you’re sitting next to your own mother. Again, gross.

I seem to remember there being a lot of attention heaped on Jamie Lee Curtis for doing this scene at the ancient age of 36. The impossible standards we hold for women, particularly women who dare to participate in the meatgrinder of Hollywood, are quite repugnant and reminds me of a joke in Forgetting Sarah Marshall as Jason Segel tries to comfort Kristen Bell by saying, “You’ve got a long career in front of you. You’ve got four years until you’re 30.”

Mimi Rogers as Mrs. Kensington in Austin Powers: International Man of Mystery

Her age at time of movie’s release: 41. Mine: 16. Difference: 25 years.

First of all, it’s noteworthy that Mimi Rogers plays Elizabeth Hurley’s mom despite being only eight and a half years older than her. I get why, considering the cryogenic storyline necessitates two hot ass women who look like they could be related 30 years apart. Fine. And secondly, I know Mimi Rogers is only in this movie for a hot minute, so why include her in this list?

Again, if you’re of a certain age and had premium cable growing up, you’ve seen certain lesser-known movies roughly a billion times because of their ubiquity on HBO, Cinemax, and Showtime. These are movies like Airborne, Just One of the Guys, or Freaked. One that nearly no one else I’ve talked to has much familiarity with is Full Body Massage starring Mimi Rogers and the guy who played Coughlin in Cocktail. Do I remember anything about the plot of this movie apart from the fact that basically the entire thing takes place over the course of the titular full body massage? Reader, I do not. I do, however, remember that Mimi Rogers spends basically the entire movie extremely naked and getting rubbed with oils by a very lucky dude as they talk about whatever for an hour and a half. I also remember that Mimi Rogers had unflappable confidence and captivating presence in this goofy movie, and any actor who’s willing to do an entire movie butt-ass naked is someone whose energy I want to luxuriate in.

She shows up right at the beginning of Austin Powers, and I’m like, “Aw hell yeah, this chick!” Then Austin gets frozen, she disappears except for a quick phone call with her daughter, and, in probably the most sincere and understated part of the movie, Austin waxes romantic about his old partner. If you’ve seen Full Body Massage (I wager you haven’t), Austin’s romantic soliloquy lands that much harder.

Ellen Barkin as Abigail Sponder in Ocean’s 13

Her age at time of movie’s release: 53. Mine: 26. Difference: 27 years.

God, Ellen Barkin is so hot in this movie. Is it the impossibly tight dresses she wears showcasing a bangin’ figure? Is it her assertive drive and unshakeable confidence throughout the film’s running time? Is it the last act where thanks to some hokey chemical Spanish Fly Matt Damon applies she gets all drunkenly horned up and weak-kneed barely able to stifle her now rampaging libido? Yes to all. It’s all delightful.

Prior to Ocean’s 13, I best remembered Ellen Barkin from the slinky, sexy, neo-noir film Sea of Love. She seemed dangerous, which made her all the sexier. In Ocean’s 13, she’s all-business until she’s not and the veil drops. In the brief time we spend with the character, it’s not hard to imagine she’s wanted this veil to drop for some time considering the one-way transactional and seemingly unfulfilling relationship she has with, oddly enough, Al Pacino again. When she gets the chance to drop it, she drops it fully and pounces on Matt Damon with vigor and enthusiasm. Everyone wants to be the one to unlock that much ferocious sensuality in someone else. That feeling will cause you to float three feet off the ground for a month.

Sophia Loren as Maria Ragetti in Grumpier Old Men

Her age at time of movie’s release: 61. Mine: 14. Difference: 47 years (!!!)

And we arrive at the impetus for this list. I hadn’t seen Grumpier Old Men in years, but it popped up on one of my cable channels and in the scene where Maria shows up at Slippery’s Tavern to try to convince Max and John to stop harassing her and give her restaurant a chance, it all came flooding back.

She enters the bar to the strains of Shocking Blue’s iconic song “Venus,” takes off her coat, optimizes her cleavage, and struts confidently toward Walter Matthau flanked by the slack-jawed expressions of the old rubes in the bar who have likely never seen such a commanding beacon of sex in real life ever up to that point. She then proceeds to take some ice out of her water, and drops it into her ample bust as Walter Matthau might as well be salivating like a St. Bernard.

Rewatching this now, and I can’t help but ask not why I was turned on to all hell at a woman 47 years my senior, but rather what red-blooded man or woman seeing this movie wasn’t? Sophia Loren is an icon. She’s funny. She’s confident. She’s undeniably sexy. And she commands a room like few others have in history. That might as well have been Helen of Troy walking through the door of that shitty small town dive to seduce, of all people, human/bloodhound hybrid Walter Matthau. I actually had a Grumpier Old Men poster in my room as a teenager which sat neatly somewhere in the lineup of posters for Tales from the Crypt Presents: Demon Knight, Jackie Chan’s Rumble in the Bronx and the John Travolta/Christian Slater vehicle Broken Arrow, a murderer’s row of movies if there ever was one.

Sure it felt weird lusting over a woman in her 60s while I wasn’t even done with puberty yet, but not nearly as weird as my friend Mike and I going to the movie Out to Sea starring Lemmon and Matthau as conmen who pretend to be dance instructors to gain entry to a cruise ship for reasons I don’t remember and then realizing we were the only two people under the age of 60 in the theater.

A few months after seeing Grumpier Old Men, I got my first girlfriend, had my first kiss, and felt like Matthau strutting around while “Stayin’ Alive” by The Bee Gees played on the soundtrack after he finally beds Sophia Loren. These things aren’t related in any way whatsoever, but I can’t think of another way of ending this piece.