10 Ways Adam Sandler Can Get His Swag Back

There's a reason why we can't get very excited for That's My Boy, and it's not Vanilla Ice's presence in it.

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Adam Sandler's early comediesBilly Madison (1995) and Happy Gilmore (1996) replay incessantly on cable television, and with good reason. Endlessly quotable and always funny, they represent the kind of innocently moronic Hollywood comedies that aren’t made often these days. Sadly, when you watch those movies now, the viewing process is frequently disrupted by thoughts of, “Damn, I miss this guy.”

We feel your pain. Nowadays, in the wake of Sandler’s worst movie thus far in his 23-year-career, the 2011 embarrassment Jack and Jill, the proposition of a new Adam Sandler comedy sounds more like a threat than a promise. And he only has himself to blame, since all of the multimillionaire’s projects come from his Happy Madison Productions, and bear his dirty fingerprints.

The latest example is That’s My Boy, an R-rated flick co-starring fellow Saturday Night Live alum Andy Samberg as the well-to-do son of a deadbeat, partying father (Sandler) who conceived the kid when he was in grade school, with his teacher, no less. Admittedly, That’s My Boy, directed by Sean Anders (who co-wrote Hot Tub Time Machine and She's Out of My League), does look like it could potentially be the funniest Sandler film since Funny People (2009), but that doesn’t dismiss its undeniable air of predictability.

Blame it on those Billy Madison re-airings, but we still have hope that our once-favorite comedic actor can make us become dedicated fans again. Here are a few suggestions to help his, as well as our, cause: 10 Ways Adam Sandler Can Get His Swag Back.

Written by Matt Barone (@MBarone)

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What’s one tell-tale sign that you’re watching an Adam Sandler movie, whether it’s one he stars in or simply produces? Nick Swardson, the Memphis Bleek to the Sandman’s Jay-Z, is there on the screen, playing a completely obnoxious character in a terribly unfunny and grating way. Or perhaps there’s the one-two combo of lesser-known Allen Covert and Peter Dante, whose faces regularly pop up in Sandler movies to marginal laughter, save for their effectiveness in the underrated Big Daddy.

And we haven’t mentioned the countless other C-level actors whom Sandler routinely casts in his movies. He’s without a doubt Hollywood’s most generous superstar, allowing his buddies to effortlessly benefit off of his own fame and glory, but it’s to his own detriment, frankly.

Unlike Judd Apatow’s crew of go-to performers (Jonah Hill, Seth Rogen, Jason Segel, Jay Baruchel, etc.), Sandler’s entourage drags his movies down, especially Rob “I’ll embarrass any ethnic group with hideously stereotypical characters” Schneider. As bad as it’d be for their careers, Sandler needs to audition several new actually-funny comedians to become his next generation of collaborators.

Could the likes of Swardson and Covert survive on their own? At best, we’d get another Grandma’s Boy; worst case scenario, though, is more awfulness in line with last year’s Bucky Larson: Born to be a Star.

Delete Dennis Dugan's phone number and email.

Not one to stray far away from his professional comfort zone, Sandler loves to work with his closest friends, a safe-bet approach that even applies to his director choices. His favorite shotcaller to duet with: Dennis Dugan, with whom Sandler first joined forced for the 1996 gem Happy Gilmore. Three years later, they re-teamed for the also memorable Big Daddy, leaving outsiders to believe that the Sandler/Dugan duo had a special kind of chemistry.

But then came the 2006 debacle The Benchwarmers, a Sandler-backed sports comedy starring the unbearable trio of Rob Schneider, David Spade, and Jon Heder, under Dugan’s control. That’s when someone in Sandler’s camp should’ve erased Dugan’s contact info from the boss-man’s Rolodex.

Yet that never happened. Sadly, You Don’t Mess with the Zohan (2008), Grown Ups (2010), Just Go with It (2011), and Jack and Jill (2011) all did happen. With the unnecessary crime-against-humanity-in-the-making Grown Ups 2 currently being shot by Dugan, Sandler really needs to wake up and smell the Rotten Tomatoes: Dugan is a hack, and he’s dragging the Sandman down into the shitty abyss with him.

Remember that those fake movie concepts in Funny People were just that: fake.

Despite being overlong, Funny People is easily the best movie that Adam Sandler has made in the new millennium. Written and directed by his longtime friend, and former pre-fame roommate, Judd Apatow, the under-appreciated 2009 dramedy knows when to be uproariously funny but also gives Sandler—playing a cancer sick and disenchanted Hollywood comedy icon, not unlike himself (save for the “cancer sick and disenchanted” business)—a character ripe with internal conflicts and emotional heft.

Some of the film’s biggest laughs come from the faux high-concept movies that George Simmons (Sandler) stars in for the huge paychecks, including MerMan, Dog’s Best Friend, Astro-Not, and Re-Do. Oh, and Jack & Jill, the ridiculous, can’t-be-real movie in which Simmons dresses in women’s clothing to play a set of twins, and… Wait, that was Sandler, not Simmons. Pardon the easy mistake.

Everything about last year’s shameful Jack & Jill, from its posters, commercials, and stunt casting of Al Pacino, mirrored the fake flicks seen in Funny People. Except that, in Jack and Jill’s case, the joke was on Sandler, not George Simmons. He needs to do himself a favor and never let us laugh at his expense like that again.

Think outside the box when casting the next romantic comedy's female lead.

In the wake of 2002’s excellent, indie-minded Punch-Drunk Love, Sandler has starred in some of the lamest rom-coms to infect cinemas. Aside from poor writing, flat jokes, and sophomoric sensibilities, these “heartfelt” flicks are often hindered by someone other than Sandler himself. To put it simply, he has awful taste in actresses. We don’t mean looks wise, mind you, because he does have quite the eye for beauties. But not ones who can act well.

Case in point: Brooklyn Decker, the first-time actress whose Sports Illustrated swimsuit body is the only thing she brings to Just Go with It. Or Jessica Biel, who, again, offers little more than physical hotness in I Know Pronounce You Chuck and Larry. Which is something that, unfortunately, can’t be said about the all-around bland Katie Holmes (Jack and Jill).

It’s not like there aren’t any sexy ladies out there who are also skilled performers and, most importantly, hilarious. There’s Aubrey Plaza, the Parks and Recreation scene-stealer who’s wonderful in the terrific new time travel comedy Safety Not Guaranteed; Alison Brie, Community’s GIF queen who killed it in the unfairly dismissed Jason Segel/Emily Blunt film The Five-Year Engagement; and, for the older crowd, Amy Poehler, the Parks and Rec headliner who’s yet to dominate the big screen in a big-time film.

Any of them would certainly hold their own. Hell, they’d all outshine Sandler in his own movie, but maybe that’s what the guy needs to recharge his batteries, so to speak.

Give cable TV a try.

It’s the popular discussion amongst Hollywood’s talking heads, one that’s been prevalent for about two years now: The tide for fictional on-screen storytelling has shifted, and, these days, the work that’s being done on cable television is largely better than what’s seen in movie theaters.

That’s why industry giants like Martin Scorsese, Aaron Sorkin, and Jessica Lange have been spending so much time concentrating on their small-screen efforts. With more hours to flesh out characters and less need to satiate major studio’s box office requirements, TV show controllers and performers are relishing the opportunities to put the art first and commerce second.

And it’s not just dramas, either. On Showtime, Edie Falco has triumphantly made us forget all about Carmela Soprano on the masterfully written and sharply funny Nurse Jackie; meanwhile, over on HBO, Sandler’s old pal Judd Apatow wisely backed indie filmmaker Lena Dunham’s Girls, all the way to critical praise and high ratings, and Seinfeld alum Julia Louis-Dreyfus found a character even greater than Elaine Boosler in the form of her Veep counterpart, Vice President Selina Meyer.

Now that Apatow has some power at HBO, it’d be a great look for Sandler if the two of them came up with a TV character full of tragedy, humor, and pathos—think Happy Gilmore without the lucrative golf hustle.

Go back on the road for a lo-fi stand-up tour.

Recently, Anaheim Angels first baseman Albert Pujols, after being traded from the St. Louis Cardinals, the team he led with his amazing hitting skills and home run prowess, couldn’t put a ball over the fence if you, well, paid him millions—literally. But now he’s, for the most part, swinging the bat like the Pujols of old, and how do you think he managed to reclaim his past dominance? By getting his ass into the batting cages and fine-tuning his craft from scratch.

The same tactic could definitely work for Adam Sandler, who once owned stand-up comedy stages as a newbie before he broke into Hollywood. He probably doesn’t think that his recent movies have sucked, but if he were to ask any filmgoer over the age of 12 to review his flicks, he’d most likely be met with downward-pointing thumbs and/or uncomfortable giggling.

So the truth of the matter is that Sandler has lost that funny feeling, and, like Pujols and the batting cage, Sandler should get back into that rookie mindset, write some new material, and take to the road for a comedy club tour. The jokes that crash and burn, abandon without sentiment; the self-deprecating anecdotes that inspire the most laughter, build scripts around them. Call it the Funny People model for rejuvenation.

Do a one-season stint back on Saturday Night Live.

Sorry, faithful Saturday Night Live watchers, but your beloved NBC sketch comedy program is going to be in serious trouble come next season. That’s because both Kristen Wiig and Andy Samberg, the show’s two funniest cast members for years now, have left SNL for the greener, more opportunistic pastures of Hollywood. We can’t blame them, either—Wiig and Samberg have kept Lorne Michaels’ baby in good standing for long enough, and, like with Steve Carell and The Office, it’s time for them to see what else they’re made of in the wide world of showbiz.

All that said, Saturday Night Live really needs to beef up its cast. Instead of searching far and wide for the “next Adam Sandler,” though, Michaels should just call the actual Adam Sandler up, offer him a fat salary, and give the former SNL all-star a chance to get back to his comedy roots.

In all of his recent movies, Sandler has basically played the same character over and over again: the repugnant yet, ultimately, lovable protagonist who cracks the occasional penis joke. Back on SNL, he’d be able to try out as many new creations as he’d like, and, who knows, the next Opera Man or Canteen Boy could be his next Billy Madison or Happy Gilmore.

Take a few years off and push for that one great idea.

To his fans’ delight, as well as the happiness of the studio heads who back his projects, Adam Sandler hardly ever takes a break. Dude has starred in at least one successful movie every year for the last 14 years, but here’s the downside: Such productivity has gradually lessened the overall quality of his cinematic output.

We’ll even be sympathetic here: It has to be damn near impossible to maintain a consistency over that long a period of time. And when fatigue sets in, so does a lackadaisical attitude, and that’s when Jack and Jill happens. So why not take some personal time, kick back with the family, and live off your insane riches earned through a succession of $100 million-plus hit movies?

Who knows, a year or two of me-time might help him to scoff off ideas like playing a woman (Jack and Jill) and starring in a movie alongside both Vanilla Ice and Rex Ryan (That’s My Boy). And it might just trigger Sandler’s imagination and provoke some fresh, left-field ideas.

Give Paul Thomas Anderson a call.

When Adam Sandler collaborated with acclaimed, somewhat enigmatic filmmaker Paul Thomas Anderson for the quirky and intelligent 2002 romantic comedy Punch-Drunk Love, highbrow critics scratched their foreheads. At the time, PTA, as cinema buffs like to call him, was the genius behind Boogie Nights (1997) and Magnolia (1998), and Sandler, bless his soul, was known for esteemed motion pictures like Billy Madison, Happy Gilmore, and The Waterboy.

So what gave? Anderson knew what we’d all soon realize: If given a dynamic and complicated role to play, one that’s still in his comedic comfort zone, Sandler can be one hell of an actor. And Punch-Drunk Love, about a businessman (Sandler) who endures seven insufferable sisters while falling in love with an eccentric stranger (Emily Watson), isn’t just the funnyman’s best movie to date—it’s one of the best rom-coms of all time.

Having only made six films in 16 years, the meticulous Anderson isn’t an easy director to coerce, but, considering their past success, it’s not unrealistic to think that the director would jump at the chance to work with Sandler again.

Even better, Anderson is currently in a dark phase—he’s following up the pitch-black 2007 character study There Will be Blood with what seems to be an equally morose play on Scientology, The Master (set for an October release). Imagine what Sandler could do with a role as rich and horrifically magnetic as Daniel Day-Lewis’ in There Will be Blood. As crazy as that sounds, wouldn’t you love the chance to see for yourselves?

Act like he gives a shit once again.

Look, we’re not saying that Adam Sandler doesn’t care about his fans here—on the contrary, he thinks about them too much. Rather than push himself creatively and see if his supporters follow, Sandler has always reheated his own stale goods just to give his easily satisfied fan base what is wants, no questions asked. But, and we’re quite aware that we’ve attacked this film numerous times in this list, an effort like Jack and Jill is, whether he realizes it or not, an insult, as if to say, “I know you’re all going to pay to see this just because I’m in it, so here goes nothing—literally!”

There once was a time when Sandler took risks, like when he signed on to make 2002’s Punch-Drunk Love, or when he worked with the reputable James L. Brooks on Spanglish (2004), or his brave decision to play a post-9/11 fractured soul in Reign Over Me (2007). Clearly, from ’02 through ’07, he had bigger things in mind for his career than fart jokes and employing Nick Swardson—yes, he gave a shit about the artistry.

Perhaps the underwhelming box office performance of 2009’s daringly dramatic Funny People left a bitter taste in Sandler’s mouth, prompting him to retreat back to his idiot-proof, and idiot-serving, methods.

But, if that’s the deal, he should go back and read Funny People’s reviews from the game’s most respected critics. Roger Ebert, for one, had this to say: “I realized here, as I did during his Punch-Drunk Love, that [Adam Sandler] contains an entirely different actor than the one we're familiar with. His fans are perfectly happy with Sandler's usual persona, the passive-aggressive semi-simpleton. This other Sandler plays above and below that guy, and more deeply.”

See, people recognize genuine talent when it’s before them. If only Sandler cared more about respect and admiration than surefire dollars and hanging out with less gifted friends.

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