The 15 most monstrous vanity projects ever made

Who could’ve predicted that trying to make a white rapper with a goofy haircut into the next James Dean would end up a massive embarrassment, except everyone? Starring Vanilla Ice as a motorcycle-riding bad boy wooing a small-town girl with his sick rhymes (example: ‘Drop that zero and get with the hero’) Cool as Ice was clearly meant to be his Purple Rain. Alas, the Ice Man is no Prince – not even the Prince that made Under the Cherry Moon – and the movie bombed with both critics and audiences. At least we’ll always have his cameo in Teenage Mutant Ninja Turtles 2: The Secret of the Ooze.

Most monstrously vain moment: Vanilla freaks out the small town rubes with an impromptu performance that at one point sees him pinning his love interest to the ground and rapping directly into her mouth.

Self-indulgence has always been Vincent Gallo’s calling card, but the indie auteur took his megalomania to another level with this grindingly slow one-man road movie about a motorcycle racer driving cross-country to reconnect with a former flame. Its lasting legacy is the war of words it sparked between Gallo and Roger Ebert after the critic eviscerated the film following its premiere at Cannes. Gallo responded by calling Ebert ‘a fat pig,’ prompting Ebert to quip, ‘It is true that I am fat, but one day I will be thin, and he will still be the director of The Brown Bunny.’ Savage.

Most monstrously vain moment: after two hours of essentially nothing happening, Gallo arrives in Los Angeles and receives graphic, unsimulated oral sex from his real-life ex-girlfriend, Chloe Sevigny.

Say what you will about Tom Cruise and his connections to Scientology, at least he’s had the good sense not to adapt any of L Ron Hubbard’s quasi-religious sci-fi gobbledygook for the big screen. That task was left to fellow true believer John Travolta, who shepherded this adaptation of Hubbard’s 1982 novel into existence and ended up killing his career for the second time. It’s not that there’s much decipherable Scientologist ideology evident in the movie – it’s that it’s bloated and incoherent, with hideous costumes and set design. In particular, Travolta gives a ridiculously hammy performance as some kind of alien warlord while looking like a trustafarian Genghis Khan.  

Most monstrously vain moment: Travolta’s drunken soliloquy at some kind of futuristic cocktail bar. 

Madonna’s entire film career could be considered a vanity project, but this remake of Lina Wertmuller’s 1974 Italian dramedy is particularly egregious, given that it was directed by her then-husband, Guy Ritchie. Madge plays a spoiled socialite on a cruise who ends up stranded on a deserted island with a hunky deckhand (Adriano Giannini, son of original star Giancarlo Giannini) she nonetheless treats like garbage and then falls in love with. Maybe it’s a bit cynical to presume Ritchie only did the movie to fund a Mediterranean vacation for him and his wife, but there’s no other way to explain why he’d veer so far from his macho crime-comedy niche, nor why no one involved seems to be trying very hard to make the thing work. 

Most monstrously vain moment: honest, any moment in which Madonna insists she can act is monstrous by itself.

One of the more inexplicable moments of the 1980s is how a New Jersey meathead telling misogynist nursery rhymes briefly became the biggest standup comedian in America. It’s even worse than that, though: at one point, Hollywood actually tried to make Andrew Dice Clay into a movie star. Thankfully, it didn’t take, and this vehicle – in which Clay transposed his ‘loud mouth mook’ persona onto an LA private eye – represented the beginning of the end of the Diceman phenomenon. That Clay’s managed to carve out a decent little acting career decades later is easily his best joke.     

Most monstrously vain moment: the car chase through a cemetery, during which Clay finds time to make blowjob jokes about the buxom corpse in the passenger seat.

Over the course of his career, Will Smith has gone from novelty pop-rapper to TV star to A-list movie star to amateur slap-boxing champion. So who’s to say he couldn’t come up with a really rad concept for a sci-fi movie? Well, someone should have, because this possibly-maybe Scientologist parable, about father and son space explorers stranded on an inhospitable post-apocalyptic Earth and co-starring Smith’s own son Jaden, is one of the bigger big-budget disasters of the last decade. The nepotism is one thing, but handing the director’s chair over to M Night Shyamalan – a guy who almost exclusively makes big-budget disasters these days – doomed it from the start.  

Most monstrously vain moment: Jaden Smith screaming ‘I’m not a coward!’ on a CGI mountaintop, then leaping off and unveiling some kind of flying squirrel outfit.

In the ‘90s, it seemed like nothing could stop Mariah Carey’s run of pop-chart dominance. Then the 2000s came, and she decided to make a movie. Even though this is essentially her own biopic, Carey is entirely unconvincing playing herself, and the script is loaded with rags-to-riches cliches. (It’s also a fairly obvious riff on A Star Is Born.) It bombed hard at the box office and cratered Carey’s career as both an actor and singer. She recovered, but the movie probably won’t receive a reappraisal anytime soon: Carey herself calls it her greatest regret.

Most monstrously vain moment: Mariah’s character, Billie, tearfully reunites with her alcoholic mother the morning after her triumphant concert at Madison Square Garden, while still wearing her sparkly stage dress.

Of the many ambitious failures Kevin Costner was involved in back in the ‘90s, The Postman deserves special commendation for being the actor’s directorial followup to the Oscar-winning Dances with Wolves. A sci-fi epic about a post-apocalyptic mail carrier touring the ruins of the United States, it’s a big, bloated bore – and notorious flop – that makes you long for the non-stop thrill ride that is Waterworld.

Most monstrously vain moment: hey, look, Tom Petty’s here for some reason! Probably so Costner – who fancies himself a roots-rocker on the side – could brag about hanging out with Tom Petty.

Someone at Warner Brothers had to have lost a bet or had some incriminating photos floating around or something to allow Steven Seagal to direct his own movie. On Deadly Ground isn’t terribly different from any of Seagal’s other generic punch ‘em ups, but there is a pronounced messianic streak running through it. Seagal cast himself as the hilariously named Forrest Taft, an eco-warrior with a white saviour complex protecting an inuit village from an evil corporation planning to build a refinery on their land. What better way to save that land than blowing most of it up? 

Most monstrously vain moment: the concluding monologue, a four-minute environmentalist speech in which Seagal-as-Taft rambles about everything from ‘alternative engines’ to corporate pollution to dying plankton.

Kevin Spacey has been accused of much more monstrous things than attempting to play a 30-something Bobby Darin while being in his late 40s, but if we’re considering only his filmography, this dismal biopic is among his worst offences. Spacey had a long-running obsession with the crooner, and thus took the full reins of this passion project: writing, directing and, as mentioned, donning a black toupee and trying to pass himself off as a ‘50s pop idol. He even does the singing himself. It’s the kind of vainglorious exercise that turns what’s ostensibly meant as an homage to a great entertainer into a creepy game of dress up.   

Most monstrously vain moment: Spacey, as Darin, performing ‘Splish Splash’ for an audience of screaming teenagers while looking like a wax statue come to life. 

Is it fair to include a movie that no one’s ever seen in full on a list like this? When the movie involves Jerry Lewis playing a clown leading Jewish children to the gas chamber during the Holocaust, it’s a pretty safe bet. Lewis, who also co-wrote and directed the film, experienced a moment of clarity during the editing process and vowed that the public would never see it, and copyright issues have so far kept it from screening anywhere. That may change, though: before his death, Lewis donated an unfinished copy to the Library of Congress on the condition that it not be shown until June 2024, at which point we may have to check Lewis’ grave to make sure he hasn’t turned on his face. 

Most monstrously vain moment: hard to say since only a handful of people have ever seen it, but the concluding moments – in which Lewis apparently ‘pied pipers’ a group of scared children into the gas chambers at Auschwitz – is cringe-inducing just to read about.

If it wasn’t for the scorching concert footage and the all-time great soundtrack, Purple Rain could’ve easily ended up a colossal, self-indulgent flop instead of one of the defining movies of the ‘80s. But Prince just had to keep pressing his luck, and his megalomania got the best of him with his next film project, a tepid black-and-white period romance he directed himself. Turns out, Prince is great at playing Prince, but playing Prince in the French Riviera circa 1930 doesn’t really translate. The soundtrack still rips, though.   

Most monstrously vain moment: the opening sequence, in which Prince spots a woman at a bar, seduces her with his lascivious piano playing, beds her and leaves, all before the credits stop rolling.

After the era-defining TV show bearing his name ended its run, Jerry Seinfeld seemed content to spend the rest of his life going to Knicks games and doing the occasional standup gig. So it struck everyone as a bit strange when, after a decade-long creative layoff, his first post-Seinfeld project turned out to be an animated movie about an insect who sues mankind for exploiting the labour of honeybees. Bee Movie has its defenders, but cramming Seinfeldian humour into what’s essentially a kids movie left most viewers a bit... bee-wildered.

Most monstrously vain moment: the whole flirtatious relationship between the anthropomorphic bee of the title (voiced by Seinfeld) and the florist (Renee Zellweger) who takes a liking to him is, let's say, off-putting.

Still flying high on the success of Rocky three years later, Sylvester Stallone slid into the director’s chair and turned out a similar underdog story about three brothers in 1940s New York trying to fight their way out of poverty via, uh, professional wrestling. Lightning did not strike twice. On the other hand, any movie that has both Tom Waits and pro-wrestling legend Terry Funk in the cast can’t be all bad.

Most monstrously vain moment: not content to just write, direct and star, Stallone also elected to mumble the closing theme song himself.

John Wayne had long dreamed of making a movie about the Battle of the Alamo, and by 1960 he had enough clout that Hollywood let him do it. And what better way to make one’s directorial debut than with a three and a half hour, ultra-conservative epic about a major historical event that doesn’t seem to care much about historical accuracy? Rumours persist that John Ford ghost-directed most of it, and he did work on the second unit, which probably explains why the battle scenes are legitimately impressive. 

Most monstrously vain moment: Wayne’s character gets drunk and goes on a thinly veiled anti-Communist rant…in what's supposed to be 1836.