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We may receive a commission on purchases made from links. (Welcome to Tales from the Box Office, our column that examines box office miracles, disasters, and everything in between, as well as what we can learn from them.) "The most visually imaginative movie Sandler has made — but it's also one of the most mind-bogglingly tasteless." Those are the words of critic Michael Wilmington writing for the Chicago Tribune in his review of Adam Sandler's 2000 comedy "Little Nicky." Though opinions certainly differ on the "tasteless" part of that equation, it is undeniable that this was the biggest movie of Sandler's career to date. It was also a critical and commercial disaster. Sandler was coming off his ascension to A-list status in Hollywood as a string of hits in the '90s turned him into a superstar. As a leading actor, he could do little wrong. "Little Nicky," whether intentional or not, was a go big or go home moment for Sandler. With a star-studded cast, a massive budget, and the guy who wrote "The Mighty Ducks" behind the camera, the high-concept comedy had a lot going for it on paper. In practice? It remains the biggest box office flop of Sandler's long, storied career. In this week's Tales from the Box Office, we're looking back at "Little Nicky" in honor of its 25th anniversary. We'll go over how it came to be, the hot streak that Sandler was on at the time, what happened when the movie hit theaters, what went down in the aftermath of its release, and what we can learn from it all these years later. Let's dig in, shall we? The film picks up after Satan (Harvey Keitel) decides not to give up his throne to any of his three sons. Adrian (Rhys Ifans) and Cassius (Tom Lister Jr.) then escape to Earth seeking to create a kingdom for themselves. In doing so, they close a portal that brings souls to Hell, leaving Satan to wither. He's forced to send his weaker but beloved son Nicky (Sandler) to Earth to bring his brothers back to Hell. Sandler was coming directly off of "Big Daddy," which was a big hit. But up to this point, most of his comedies had been situational comedies that just relied on him doing his thing in a wacky situation. When it came to "Little Nicky," it was more ambitious from the start, tracing its roots to director Alan Parker's psychological horror film "Angel Heart." "I was watching 'Angel Heart' with my friend, we were watching Robert De Niro's character, and I just said, 'Wouldn't it be a funny movie if somebody plays the son of the Devil and he's kind of a goofball?' And we went off of that," Sandler explained in a 2000 interview (via ScreenSlam). "[Nicky is] actually based off of a kid I knew in high school," Sandler elaborated. "He used to talk a little out the side of his mouth, and he knew a lot about rock 'n roll." When it came time to fill the director's chair, Sandler turned to his friend Steven Brill, who had previously directed Disney's now-cult-favorite "Heavyweights," in addition to writing "Mighty Ducks." Brill previously had minor roles in "The Wedding Singer" and "Big Daddy." Now? He was going to be behind the camera for Sandler's most expensive movie to date. "Little Nicky" was set up at New Line Cinema, with the studio ultimately putting up a very hefty budget in the $80 million range. That is a great deal for a comedy, especially when we consider that, adjusted for inflation, it would be like making a $150 million movie today. But the world that Sandler envisioned alongside another frequent collaborator in Tim Herlihy ("Billy Madison") and Brill wasn't small — or cheap. As Brill explained in a 2000 interview with The Tufts Daily, they had their work cut out for them: "This one was a little tricky because we had to create a science-fiction world and do a lot of thinking that we don't normally have to do. We had to actually write longer and harder on this just to get all the rules down." New Line had reason to bet on Sandler. He was riding very high at the time. "Billy Madison" was a modest hit that put him on the map, with "Happy Gilmore" doubling down. His hot streak wasn't totally unbroken as the disappointment that was "Bulletproof" was in the mix, as was a minor role in Bob Saget's cult favorite comedy "Dirty Work," but by and large, Sandler was on a roll. The hits in that streak included the much-beloved "The Wedding Singer" ($123 million worldwide/$18 million budget), "The Waterboy" ($190 million worldwide/$23 million budget), and the aforementioned "Big Daddy" ($235 million worldwide/$34 million budget). Those movies all had one thing in common: reasonable budgets. Be that as it may, New Line felt it was prudent to bet on Sandler's big, bizarre heaven and hell comedy. Part of that had to do with the stacked cast, which included Sandler regulars like Peter Dante and Allen Covert. But it also included acting legends like Harvey Keitel as Satan, Patricia Arquette ("Lost Highway") as Nicky's love interest Valerie, and even "Pulp Fiction" director Quentin Tarantino as a preacher. "I had a lot of fun doing that. That was really cool," Tarantino said in 2000 to Ain't It Cool News. "It started off, he was just one little joke, and then Adam and all his buddies he makes his movies with, they just really liked the character." The cameos didn't end there as rock legend Ozzy Osbourne also had a very memorable bit part in "Little Nicky." The stacked cast, coupled with the need to literally bring both heaven and hell to life on screen, didn't come cheap. Between actors getting their checks and extensive CGI, the cost ballooned to three to four times what Sandler's other comedies of this era would have cost. In 2000 and especially now, the list of movies that can truly justify a budget of that size, in terms of expected audience, isn't long. As New Line would learn the hard way, this movie wasn't going to make its way onto that list. It's not that Sandler was ever a critical darling or anything, but even with that being said, Sandler's big Heaven and Hell comedy was largely eviscerated by critics upon release. To this day, it boasts a 21% approval rating on Rotten Tomatoes. When a movie costs this much money, it needs all of the help it can get. Word of mouth wasn't going to be of service here. "Little Nicky" hit theaters on the weekend of November 10, 2000. For whatever reason, New Line didn't try to capitalize on the Halloween season despite the movie's premise. All the same, it opened to $16 million domestically, coming in at number two behind "Charlie's Angels" ($24.6 million) in its second weekend. Working in its favor was the fact that it also opened against another big-budget flop in "Red Planet" ($8.7 million). Too much was working against it. Movies like "Meet the Parents" were still in the middle of huge box office runs. Even another Hell-based comedy in "Bedazzled" was in the top 10 that weekend, pulling in $2.5 million on its fourth weekend. It only got worse when "How the Grinch Stole Christmas" opened to a massive $55 million following weekend, while "Rugrats in Paris" ($22.7 million) also had a strong debut, while Sandler's latest collapsed. "Little Nicky" finished its run with $39.4 million domestically to go with $18.8 million internationally for a grand total of $58.2 million worldwide. That didn't even come close to covering the budget, let alone marketing expenses. It was a huge flop. Sandler's had some flops. "That's My Boy" ($58 million box office/$70 million budget) is up there and director James L. Brooks' "Spanglish" ($55 million box office/$75 million budget) is pretty close to taking the cake but, at the end of the day, "Little Nicky," in terms of its pure box office performance, takes the cake. Sandler recovered quickly with "Mr. Deeds" ($171 million worldwide/$50 million budget) coming out in 2002, with other hits like "Anger Management" and "50 First Dates" soon following. Along the way, the tide also started turning for "Little Nicky." Anecdotally, I can tell you this was very much a sleepover favorite in my youth. Blockbuster Video helped its cause, as did cable TV. It found its audience. Even Roger Ebert, in his day, called it "the best Sandler movie to date." Writing for /Film in 2000, Evan Saathoff said of the film, "Now, rather than being the one black mark on an otherwise perfect career, 'Little Nicky' feels like a refreshingly unique flavor, the only Adam Sandler film where you can see a guy with boobs growing out of his head." Cara Delevingne also declared herself a big fan on "The Graham Norton Show." The folks at Shout! Factory also released a collector's edition Blu-ray several years back. The tide has turned so much that "Happy Gilmore 2" director Kyle Newacheck suggested making a sequel. "I bet we could do something really crazy with Little Nicky," Newacheck said to Comicbook.com. "I feel like Little Nicky in the fantastic realm would be really able to call attention to some crazy s— going on in the world right now." Whether or not New Line ever made their money back is unknown but there is something to be said for the value that a box office flop people like brings to a studio's library as opposed to a flop that winds up lost to in the annals of cinema history. All the same, in an era when Hollywood's budget problem has only gotten worse, spending that amount of money on this movie still stands out like a sore thumb. The movie business is never a sure thing but over-spending – especially to this degree – is always a bad idea. It rarely works out and on the odd chance it does, it's more of the exception that proves that rule. The unfortunate result is that Sandler played it more safe with his comedies for most of the rest of his career, though he did venture out of his comfort zone for dramas like Paul Thomas Anderson's "Punch Drunk Love" and, more recently, "Uncut Gems," among others. In the comedy realm, he's content to make movies for Netflix like "The Ridiculous Six" and "Hubie Halloween," serving the audience that he's loyally served for more than 30 years. Had "Little Nicky" been an outright hit, who knows? Maybe Sandler would have made more off-the-rails comedies. But the bigger thing is that the box office is not nor has it ever been a judgment against a movie's perceived quality. Great movies flop all the time. Bad movies often make lots of money. History truly gets to decide a movie's fate and, in this case, time eventually caught up with it.
