THE CLUELESS WEDDING SINGER: Bonus Valentine Day’s Double Feature!
The beautiful thing about traditions is that most of them are created by accident.
My entire media-watching year is built off of accidental traditions. For instance, there are certain episodes of The Office and The X-Files (“Stress Relief” and “Leonard Betts”, respectively) that my wife and I only watch in January because they originally aired after the Super Bowl. Also, there’s an episode of Community I only watch on my birthday (“Advanced Mixology”, naturally). Stuff like that. I bet we all have accidental traditions like this; it’s a fun way to go through the calendar, and having little dumb things to look forward to in the future can help alleviate the pain and pressure of the present.
To that end, one of my absolute favorite accidental traditions just happens to be a bespoke double feature we watch every Valentine’s Day.
I don’t remember exactly why my wife and I decided a couple of years ago to pair 1995’s CLUELESS with 1998’s THE WEDDING SINGER around February 14th, especially since neither are explicitly about Valentine’s Day. Why not pick from the pantheon of explicitly romantic movies? Hell, why not the 2010 masterpiece VALENTINE’S DAY? Who can resist a movie that gives you Jennifer Garner, Jamie Foxx and two Taylors (Lautner and Swift)?
Well, me. And my wife. Because we watch CLUELESS, one of her all-time favorite films, and THE WEDDING SINGER, a sneaky great comedy starring someone whose movies were outright banned from my house as a kid. Both are offbeat love stories that have their own unique affectations (the famous valley-girl speak in the former, the “habada-doo” manchild Sandler stuff in the latter) that surround a sweet, beating heart at their centers. Both contain at least three or four lines that we quote to each other constantly. Both have great soundtracks!
And both form the basis of one of my favorite traditions of the year. And now I thought I’d share it with you, too! Won’t you be my valentine, dear reader?
CLUELESS (1995)
Directed by: Amy Heckerling
Starring: Alicia Silverstone, Paul Rudd, Brittany Murphy, Stacey Dash, Breckin Meyer
Written by: Heckerling
Released: July 19, 1995
Length: 97 minutes
One of these days, I really oughta read Emma. To be honest, Jane Austen’s oeuvre is probably one I need to work through as soon as possible, if only because so much of modern fiction seems to be in its debt. I mean, she only wrote seven books in all. That doesn’t seem so hard. Yes, that’s more books in total than I’ve read in the last five years, but still!
Well, until I do, I’ll have to make do with the dozens of film and television adaptations that have bubbled up since the early 1940s. Some of the most famous ones include the Greer Garson-Laurence Oliver-starring PRIDE & PREJUDICE, the Ang Lee-directed, Emma Thompson-starring-and-penned version of SENSE & SENSIBILITY back in 1995, the 1996 Gwyneth Paltrow vehicle EMMA, and the 2005 PRIDE & PREJUDICE adaptation that continued Keira Knightley’s run as the 2000s queen of the period piece.
Of course, of all of them, the one that probably still has the most clout in popular culture is 1995’s CLUELESS.
Now, I can’t speak to Amy Heckerling’s teen classic as it stands as an Austen adaptation; again, haven’t read the book! And I usually despise “classic literature…but modern!” movies (like, say, the characters of Romeo & Juliet calling their guns swords, but never mind). But, I think when one is taking a beloved classic book and setting it in modern times, it’s almost always preferable to take the source’s basic structure and plot, but then just let the rest fill out as appropriate from there.
I might have resented this movie if it was called EMMA. But it’s not. It’s called CLUELESS.
And a dandy title it is! Of course, the title word is spoken by our hero, Cher Horowitz (Silverstone), a Beverly Hills teenager who, when she’s not shopping on Rodeo Drive with her best friend Dionne (Dash), is using the skills she’s picked up from her litigator father (Dan Hedaya, perfect as always). In response to an underwhelming report card, she’s able to negotiate with most of her teachers to get them arbitrarily raised (to provide insight into their relationship, her dad literally could not be prouder of her at this revelation). For the remaining holdout, Mr. Hall (Wallace Shawn, perfect as always), she decides to play matchmaker, sending and facilitating love letters between him and another teacher, Miss Geist. Once they get together, the newly happy Mr. Hall renegotiates Cher’s grade, and mission is accomplished. Except…now Cher has the bug to continue to do good deeds. Is this because of seeing how happy Mr. Hall is? Or is it to prove to her socially conscious stepbrother, Josh (Paul Rudd), that she can be a good person? Haven’t a clue.
Enter Tai Frasier (Brittany Murphy), a shy, awkward new girl in school who’s, well…title of movie. Cher has her new project: build up Tai’s confidence, get her to stop mooning over stoner Travis (Meyer) and hook her up with Elton (Jeremy Sisto), a vain boy from a legacy family who thinks it would just make “more sense” to get with a rich girl like Cher.
What I’ve always loved about CLUELESS is that it’s able to make a mountain of social observations about the way rich teens can be, how they develop, how kids these days talk and dress, and especially how flawed they really can be, without the movie ever really getting vicious or actively condescending. Cher clearly has a good heart and, despite her shopping-and-boys-filled world, has some brain cells to rub together. Her oral recitations in Mr. Hall’s class have some real thought behind them (in their own way) but with no clue as to how to form a verbal presentation, or even how to speak in a professional manner. She wants to date a good guy that has some class, but misses the obvious signs that he’s gay. She genuinely wants to help Tai and be her friend, but gets miffed when her glow-up works too well, and Tai starts getting too popular. By the time Tai starts sniffing around Josh, Cher realizes the bitter truth: she’s in love with her stepbrother*.
*Yeah, the famous CLUELESS “incest” plot turn. Here’s the thing: it seems insane describing it in writing, but you truly never question it at all when actually watching the movie. True, it’s explained over and over that they’re not blood related, but I think it’s more that our brains just accept that Alicia Silverstone and Paul Rudd are both gorgeous and should be having sex with each other.
Cher has taste. She has thoughts. She’s got a good soul. She’s just…well, title of movie.
I know it seems like a waste of time to break down the plot of a movie that I guarantee every single person within ten years over/under my 1988 birthdate has seen at least once. But I do so in order to remark how much the movie effortlessly crams into itself over the course of 97 minutes. It covers basically one entire school year, as well as the entirety of a 1000 page book. And it never feels leaden, and certainly never boring. CLUELESS remains effervescent and light on its feet, no doubt due to its script, which manages to take 90s teenage-speak and turn it into art. The amount of quotable dialogue could be spun off into another article all its own; Alicia Silverstone’s acidic delivery of “as if” affixed in stone the phrase’s status in pop culture forever, while Brittany Murphy makes the phrase “you’re a virgin who can’t drive” sounds akin to poetry.
(For my money, the delivery of the movie is Cher’s dad bellowing at Tai to “get outta my chair!”)
It’s also got a cast for the ages. Think of all the people we’ve already mentioned in this space. Paul Rudd is dreamy and witty. Stacey Dash, god bless her, is the perfect foil to Silverstone, who deserved a much bigger superstar window from this performance than she was ultimately afforded. Dan Hedaya and Wallace Shawn provide their signature weirdo character energy. Breckin Meyer is simply divine as the sweet stoner slacker that is so obviously a better match for Tai than Elton would ever be. Speaking of Elton, Jeremy Sisto imbues him with the right balance of patience and arrogance. Yet, somehow, we haven’t even had time to mention my favorite of the bunch. I’ve managed to not yet mention Donald Faison or his character Murray once. The guy gets, like, five or six of my favorite lines in this whole damn thing. His finest moment might be his response to Dionne screaming at him for an explanation as to why he’s getting his head shaved in the bathtub at a party: “cause I’m keepin’ it real!”
(Oh, and the Mighty Mighty Bosstones appear as themselves and sing two whole songs, which always cracks me up. I love the Bosstones, but I’m desperate to know the series of decisions that led to them showing up in CLUELESS.)
Finally, even if CLUELESS were a boring slog, it would still be worth revisiting just for how damn colorful it is. Seriously, in an era where there appears to be an ongoing, neverending debate about how dark, drab and flat mainstream movies are becoming, CLUELESS feels like it’s filmed on another planet. The yellows! The pinks! It’s just a lush watch, one enhanced by a big screen appearance. I’m not kidding when I say the moment where Cher mindlessly wanders around Beverly Gardens Park before she finally realizes, duh, she’s in love with Josh and the fountain behind her lights up in a gorgeous pink and blue…it gives me minor goosebumps every time. Just a couple of them, but they’re there all the same.
CLUELESS manages to be satirical without ever being nasty, witty without being self-satisfied, and romantic without dipping into insincerity. What could be better than that for Valentine’s Day?
THE WEDDING SINGER (1998)
Directed by: Frank Coraci
Starring: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert
Written by: Tim Herlihy
Released: February 13, 1998
Length: 96 minutes
I think the majority of my film tastes developed mostly out of a concerted effort by my mother to keep Adam Sandler as far away from me as possible.
To be honest, I get it. I was an impressionable kid, prone to imitating the cadences of the characters I saw on TV. If I saw the Animaniacs sarcastically take down Dr. Scratchansniff or Abraham Lincoln or whoever, I would walk around the house, talking and singing like Wakko Warner. If Garfield made one of his pithy remarks about Monday, you can bet I’d be repeating it at the dinner table on Tuesday. My mom eventually had to develop a mindset of risk mitigation; if this was how it was going to be for the next decade, then at the very least, she would do her damndest to avoid me screaming about getting into your hole or yelling “t-t-t-today, junior!”.
Evoking Adam Sandler’s name at home, then, was tantamount to pledging allegiance to the devil; it just wasn’t done. My only real knowledge of Sandler’s career was through cultural osmosis from my friends, all of whom seemed to be pretty up to date with whatever new big Happy Madison comedy was coming down the pike. I missed the boat on BILLY MADISON, HAPPY GILMORE, THE WATERBOY and BIG DADDY. Luckily, I didn’t really feel like I was missing out on anything, so I was able to take this restriction in stride. After all, Sandler was comedy for dummies, so this must mean I was secretly a very smart little boy.
Anyway, as so often happens, I’ve since seen most of his big comedies as an adult, as well as his years-long tenure on Saturday Night Live. Although none of them are my favorite things in the world or anything, I understand the appeal. The comedy is crude and aggressive, but is also playful and frequently bordering on absurdist. At his best, the screaming and acting out that is such a staple of Sandler’s comedy persona is masking a genuine kindness (Sandler characters are often very nice to old women). It’s no surprise to me that filmmakers like Paul Thomas Anderson and the Safdies have, over the years, tried to analyze and hone the “man-child” essence of Adam Sandler.
And, of course, it helps that the man himself appears to be a sweetheart, both to his friends and family. Yes, the fact that he casts basically the same handful of people in every single one of his movies can prove a little limiting (especially since, all due respect to folks like Rob Schneider, I don’t find many of them all that funny), but it comes from a sincere desire to keep himself surrounded by people he loves, as well as to take care of them. The depth of the wound from Chris Farley’s death that’s been left on him remains palpable; I don’t blame Sandler for never wanting to waste another second with loved ones again.
That innate weird kindness and core sweetness informs the second movie of this Valentine’s Day double feature, THE WEDDING SINGER, which is, I think, the second Sandler movie I ever saw? The first was the less-than-beloved LITTLE NICKY, which I saw at a friend’s house because it was said friend’s favorite movie at the time. I was long past the age of “b-b-but my mommy would be mad!”, so I gave it a shot. It was fine, although I didn’t really quite get the big deal. It was creative, a little strange, a lot crude, and featured Sandler screaming and doing a weird voice. It was fine!
Then, a few years later, a different friend put on THE WEDDING SINGER, and it caught me a little by surprise. Don’t get me wrong; it’s still got Sandler screaming and acting up, and there’s the kind of strange, dirty humor like you’d expect (a child gleefully calls a woman a bitch early on). Because it’s the 90s, there’s even some sketchy transgender humor* for good measure. You’d never mistake it for a Merchant Ivory flick or anything.
*Alexis Arquette’s character in this is interesting to me, as well as other character’s reactions to him. On one hand, George is part of the band family, and he’s treated with a certain amount of dignity by Robbie, which I find really sweet. On the other hand, most of the jokes aimed at him are basically just “look at the annoying weirdo”, which, although probably 80s-era-accurate, don’t allow for any sort of turn or victory for him to pay it off just a little.
But. But. At the movie’s core, it’s a straight romantic comedy, with all the cheesy hallmarks you’d expect from a 90s love story, even though this one’s set in the 80s. Guy (Robbie Hart, the titular wedding singer, played by Sandler) gets dumped by fiance, then meets girl (waitress Julia Sullivan, played by Drew Barrymore), guy falls in love with girl, girl is set to marry asshole other guy (Matthew Glave’s Glenn Gulia), girl wants to be with guy, connections get missed, until guy swoops in at last second to win girl over. For all the weird Steve Buscemi business, and rapping grandma-type humor, THE WEDDING SINGER really does have an old-fashioned spirit to it.
And the funny thing about it all is that it all actually works. You get genuinely invested in Robbie and Julia. You want them to get together. When obstacles get in their way, you’re crestfallen. When Glenn does the standard “douche fiance” act, indistinguishable from others of its kind, you legitimately want to beat the shit out of him. You’ve seen a million moments like the one where Robbie runs over to Julia’s home the night before her wedding to tell her how he really feels, only to see her ecstatically rehearsing her speech in the window of her room (unbeknownst to him, she’s forcing herself to smile her way through a speech she doesn’t want to give). But, when it happens here, you go, “oh no!”, not “oh, brother”.
The reason it works, I suspect, is because Sandler and screenwriter Tim Herlihy approach it all with sincerity. THE WEDDING SINGER isn’t really a parody of romantic comedies*, and therefore, it doesn’t aim to eschew its trappings. Instead, they do something I don’t think anyone had seen before by 1998: they take the Sandman man-child act, the one who went on Weekend Update to put a shoe on his head and call it a Halloween costume, the one who hallucinates a giant penguin stalking him in BILLY MADISON, who constantly loses his temper in HAPPY MADISON….that persona gets filtered through the prism of a guy we might actually recognize as being part of the same plane of existence the rest of us reside in. Robbie Hart loses it here and there, but only because he’s in pain. He’s a goofy loser, but he’s a working man loser. He has loser friends, but they’re all supportive. I’ve never known a Billy Madison, but I’ve met a few Robbie Harts. In another timeline, I could have been a Robbie Hart.
*It is, however, a knowing parody of the 80s, although it is one that is relatively in control. One line winkingly predicts the incoming break-up of Van Halen, and there’s a hilarious off-camera remark about the death of JR Ewing, but other than that, there’s not a ton of “whoah, remember that?” stuff.
In this sense, THE WEDDING SINGER might be the most consequential movie in the entire Sandler canon. It’s the one that made it possible to take all of the “habada-doobie” stuff and turn it into something more. Without this, I don’t know if we would have gotten PUNCH DRUNK LOVE or UNCUT GEMS. And, yes, it’s not like Sandler went to only make probing character studies from here on out; his 00s and 10s canon is littered with movies I’m probably never going to check out (sorry, Jack and Jill and Chuck and Larry). But, the mere fact that he dropped a sincere sappy rom-com in the middle of a run of movies championed by adolescent boys? I’ve always found that interesting.
Who in the world could sing “opera man bye bye” on SNL in 1993, then legitimately bring years to your eyes a mere five years later by singing “I wanna grow old with you”? Turns out, only one. Who would have thought?
P.S.: If you thought I was ending this article without mentioning Jon Lovitz’ glorious cameo, you don’t know me at all. I say “he’s losing his mind, and I’m reaping all the benefits!” to myself every night before going to bed.
