From Justin to terrible: 21 unfortunate cinematic pop-star vehicles

It doesn’t speak well for the magnetism of your leading man when a studio decides to surround him with not one, but three loudmouthed and aggressive sidekicks meant to inject some energy into the proceedings. Lance Bass, the then-closeted gay member of ’N Sync whose star wattage rests largely on being genial and inoffensive, was presumably given this misguided 2001 project after Justin Timberlake ran screaming from the script. (Inexplicably, he returned to it to play a mincing queen stereotype in a cameo, as though nervous producers wanted to double down on the “Nope, no gay stuff to see here!” shielding of Bass’ real-life sexuality.) As , On The Line is basically a feature-length “Missed Connections” ad, with Bass and his douchebag friends running around Chicago trying to track down a woman (Emmanuelle Chriqui) with whom he supposedly develops a red-hot bond after a five-minute train ride in which the two discover—get this—they both love the Cubs. What a crazy world! The film’s quality sinks even below the level of its romantic leads’ charisma, leaving audiences to wish they had waited a few months to check out the “still bad but at least tolerable” version of this story, . [Alex McCown-Levy]

Eminem successfully turned his troubled past into a compelling hip-hop biopic with , so it seemed only natural for his protégé 50 Cent to do the same. But whereas 8 Mile had Eminem’s raw vulnerability—and his rapping—to redeem its occasional lapse into cliché, Get Rich Or Die Tryin’ has to make do with Curtis Jackson’s mush-mouthed non-presence, a performance so wooden it takes getting shot for him to show any signs of life. The combination of director Jim Sheridan’s sluggish, museum curator’s pacing, the rote drug dealer drama, the central casting stereotypes, and—oh yeah—almost zero rapping, makes for a tiresome slog meant to chronicle 50 Cent’s rise to stardom, yet mostly leaves you questioning why he’s a star at all. Strangely, while Eminem balked at an acting career, Jackson continues to rack up roles in direct-to-video thrillers Robert De Niro doesn’t remember making, movies where he strains to earn sympathy by getting cancer, and series on Starz. Like the title says, you at least have to admire his persistence. [Sean O’Neal]

Crossroads should have been the ideal pop-star vehicle for Britney Spears, who at the time of its production in 2002 was one of the biggest music superstars in the world. Everything about the film seemed geared to play to her strengths: Spears plays a shy girl who writes poetry and discovers her abilities as a vocalist make for a perfect combination of soon-to-be pop star. (There’s a scene where she puts the “poetry” of her hit song “Not A Girl, Not Yet A Woman” to some piano chords, to presumably deafening shrugs from the audience.) The rest of Shonda Rhimes’ script is a scrambled, ill-conceived mess involving three friends who decide to take a road trip. Taryn Manning’s Mimi is pregnant from being sexually assaulted, but still wants to head West for a music audition. Zoe Saldana’s Kit is visiting her boyfriend, who—what a coincidence—turns out to be Mimi’s rapist, because this movie is all about the good times. And Spears’ Lucy surprises her birth mother, who reveals she wishes Lucy had never been born. How anyone thought this would be a bubbly hit beggars belief; the studio even brought in Tamra Davis, the former music video director who for several years was the go-to helmer for films attempting to turn untested young SNL cast members into movie stars (CB4, Billy Madison, Half Baked). Alas, Britney Spears was no Adam Sandler; she wasn’t even a Jim Breuer. And lo, audiences saw two roads diverging in front of them—and they chose the one less traveled by Crossroads. [Alex McCown-Levy]

When it came to finding someone to play Australian folk hero Ned Kelly—the stout, bushy-bearded Irish immigrant who robbed and murdered his away across the Outback—producers naturally had only one man in mind: willowy British rock star Mick Jagger. The Rolling Stones singer was picked (displacing Sir Ian McKellen, according to film historians) by executives who believed he’d bring in a young, hip audience, and who made sure his name dwarfed Kelly’s on the posters. Not even the debacle surrounding Jagger’s debut in Performance, released earlier that year, could have predicted how misguided this decision was. Jagger’s casting was met swiftly by protests from actors’ unions and even Kelly’s own descendants; the production was plagued by injuries, illness, and wildfires; and Marianne Faithfull, cast as the female lead, was so devastated by her collapsing romance with Jagger, she attempted suicide shortly after arriving in Australia. So it’s no wonder Jagger didn’t much feel like promoting Ned Kelly once it finally came out, which certainly didn’t help a film that—while beautifully shot, and featuring a soundtrack of Shel Silverstein songs performed by Waylon Jennings and Kris Kristofferson—is mostly a turgid affair, alleviated only by Jagger’s silly brogue and the sight of his pillowy lips perched atop an Amish neckbeard. Although he would take another stab at acting with films like 1987’s Running Out Of Luck and 1992’s Freejack, Ned Kelly was enough to sour Jagger—and producers—on his being a movie star for decades. “That was a load of shit. I only made it because I had nothing else to do,” he spat defensively upon Ned Kelly’s release. Fortunately, he found plenty of other ways to stay busy. [Sean O’Neal]

Sting should’ve been coming from a place of strength when he starred in the 1985 Frankenstein adaptation The Bride. His post-Police solo music career was going swimmingly, courtesy of the successful The Dream Of The Blue Turtles LP, and Janet Maslin singled out his acting talent in her otherwise dire review of 1984’s Dune. Unfortunately, Sting and co-star Jennifer Beals didn’t have much to work with where The Bride’s script was concerned. The film couldn’t decide whether it was supposed to be a period romance, fantasy-tinged comedy, or straight-up horror movie. Instead, The Bride just came across as an unevenly paced mess that drags for the first half and then crams in all the plot denouement and engaging action in the last bit. Although Sting displays steely menace near the end, his Baron Charles Frankenstein is an unsympathetic character who cartoonishly broods and pouts over his inability to control and conquer Beals’ Eva, a lab creation meant to pair off with the more appealing monster, Viktor. Frankenstein’s humanity and empathy is what makes the book endure, but The Bride is just deathly boring, and offers little incentive to care for any of the human characters. [Annie Zaleski]

Even in the pantheon of pop-star vehicles that utilize the time-honored tradition of turning the artist’s backstory into a souped-up melodrama, Glitter holds a special place—and not just because for the film’s disastrous reception. Glitter follows Carey’s starry-eyed young singer as she transforms from anonymous nobody into massive superstar, all while maintaining one of the most dead-eyed gazes in the history of leading performances. The film came right during the transition in the singer’s career from demure performer famous for her vocals to woman on the verge of a nervous breakdown. She happily recovered, but for a time, Glitter and its attendant fallout looked like it might permanently damage Carey’s star wattage. Instead, the film remains a notorious flop, and Carey’s seeming lack of understanding of normal human behavior and how to emote lends an extra aura of fascination to her misbegotten big-screen outing. It’s unclear what happened between Glitter and her decent performance in , but some anonymous acting coach out there deserves a Special Achievement In Not Sucking Anymore award. [Alex McCown-Levy]

Goofball hip-hop trio The Fat Boys always walked the line between good-natured clowning and out-and-out novelty on their albums, which married dexterous rapping and beatboxing skills with self-deprecating jokes about eating everything in sight. But they crossed fully over into self-parody with Disorderlies, a film from Michael Schultz—who’d put their likable personas to good, sparing use in Krush Groove—that casts the group as a streetwise Three Stooges, hired to care for a crotchety old billionaire (Ralph Bellamy) whose greedy nephew is hoping they’ll bumble him to death. Many, many jokes about The Fat Boys being unusually fat boys follow, as do scenes where Bellamy squawks lingo like “Step off, homeboy”—all culminating in that classic ’80s denouement, the freeze-frame high-five. Although Disorderlies would end up taking care of the many people who probably caught it on its perpetual premium cable run in the ’90s, its box-office failure smothered The Fat Boys’ film career before it ever got started. [Sean O’Neal]

American Idol’s debut season was a bona fide ratings and cultural phenomenon, thanks largely to the irresistible charms of the eventual winner, Kelly Clarkson, and the first runner-up, Justin Guarini. To keep the good vibes going (and cash flow positive), Idol’s production company, 19 Entertainment, decided to to film a lighthearted, beach-set rom-com/musical starring lightly fictionalized versions of themselves. What could go wrong? Plenty, as it turns out. The script for From Justin To Kelly, written by Kim Fuller, brother of Idol mastermind Simon Fuller, was formulaic and predictable. The Idol vets spend the movie dodging contrived obstacles (like a double-crossing friend of Clarkson’s who tries to woo Guarini) in between choreographed dancing and singing numbers that resemble Britney Spears cast-offs. Clarkson and Guarini, who worked well on Idol as friendly competitors, made an awkward and insincere romantic couple, mainly because the latter came off as creepy and possessive. This factor most of all robbed From Justin To Kelly of any potential redemption by kitsch. The film was so bad that in 2005, the Razzies named the film “Worst ‘Musical’ Of Our First 25 Years.” Clarkson tends to agree: In 2015, she told she pretends the movie doesn’t exist and, in fact, “just want[s] it to go away.” [Annie Zaleski]

Would Bones be better without Snoop Dogg, its very reason for being? The case is compelling. Somewhere in here, there is a campy blaxpoitation redux, its weirdly involved mix of gentrification, revenge, slumber-party murders, and rap-video iconography creating something at least watchable. But in 2001, Snoop had just begun his transformation from preternaturally laconic California foil to goofy, weed-scented self-parody. (In just three years, he would reach his nadir, as Huggy Bear in the Starsky & Hutch remake.) He cannot act, which is par for the course with pop-star vehicles, but his scenes are weirdly integrated (mostly via flashback) and even more weirdly staged (he spends most of the movie standing stock-still in a leather coat). Unwilling to push Snoop outside of his comfort zone, director Ernest Dickerson instead contrives to have him endlessly deliver sneering one-liners for a solid half of the film. The result fails to be either a good blaxploitation movie or an entertainingly bad Snoop Dogg vehicle, opting, instead, for a dispiriting third path: another boring millennial horror flick, filed alongside and . [Clayton Purdom]

To figure out just what went wrong with this screwball-comedy vehicle for Madonna, you’d have to begin with the title. Who’s That Girl? suggests a lack of familiarity with the performer, who, by the film’s debut in 1987, had already scandalized MTV audiences and appeared in three movies. But some of those previous roles were throwaways, so in 1987, Madonna was ready to reinvent herself and give comedies another go. She tapped James Foley, her close friend and video director, to helm Who’s That Girl? Madonna was also out of her depth, affecting an odd, Betty Boop-like voice throughout the entire film. The pop singer’s portrayal of a bleached-blond manic pixie dream-type who leads Loudon Trott (Griffin Dunne) on a merry chase was far too mannered, despite ostensibly being molded to suit her. Dunne’s character wasn’t the only one who failed to keep up. Foley, who would make more questionable choices with Fear and the upcoming Fifty Shades Darker, couldn’t match the energy of the leads’ onscreen antics. It wouldn’t be the last time Madonna struggled to play herself convincingly, but the accompanying soundtrack and tour were hits, which must have taken some of the sting out. [Danette Chavez]

John Mellencamp made his film debut directing and starring in 1992’s Falling From Grace, a Larry McMurtry-scripted drama about a music superstar who loves small towns, little pink houses, Jacks and Dianes, etc. The warm-ish critical reception for what was essentially a roman à clef encouraged Mellencamp to give the acting game another go more than a decade later. Unfortunately the 2001 thriller After Image required Mellencamp to make a far greater transformation than simply deleting “Cougar” from his name: Playing a former crime scene photographer who falls for a deaf psychic, then finds himself stalked by a serial killer, the singer allows his silly Van Dyke beard to do most of the character work, portraying inner torment as a sort of vaguely dyspeptic boredom. Meanwhile, the film sags under tedious dream sequences, unnecessary subplots, and endless, moody stares out of windows, across lakes, down alleyways, and generally anywhere that might have something more interesting going on. While Mellencamp has hinted over the years that he could have been a movie star if he’d only accepted the part he was offered in Thelma & Louise—a role that eventually went to Brad Pitt—After Image begs to differ. [Sean O’Neal]

Susanna Hoffs was at peak Bangles popularity when her momager Tamar Simon Hoffs decided to star her in 1987’s The Allnighter, which she wrote and directed. It actually had a lot in common with a movie released the year before, Modern Girls: a blond, brunette, and redhead trio of girlfriends learn all about life in one epic night. Modern Girls went clubbing, but The Allnighter was about the night before college graduation, with Hoffs and her friends Dedee Pfeiffer (Michelle’s sister, in her first of two appearances on this list) and Joan Cusack videotaping their last hurrah. In Hoffs’ monumental evening, she flirts with an older guy (’ Michael Ontkean), falls in love with the boy next door, and bails her friends out when they’re picked up as prostitutes, grappling with an obviously distraught Pam Grier as a prison guard. Mostly, though, Hoffs just displays her considerable lack of acting ability (foolishly, the movie never has her perform any music on screen, although she sings a few cuts on the soundtrack). Worst of all is her mom directing her steamy sex scene, artfully and mistily framed to make sure her daughter didn’t expose any accidental nudity. Hoffs wisely stayed away from the screen after that, except for a few appearances in Austin Powers’ band. [Gwen Ihnat]

Some eight years after “Achy Breaky Heart,” and at least six years before he’d land his career-defining role of “Miley’s Dad,” Billy Ray Cyrus capitalized on his moment between fame to fulfill his mullet’s lifelong dream of starring in a low-budget action movie. Radical Jack saw the sort-of-country singer star in this sort-of-entertaining riff on Road House, playing an ex-CIA agent and Navy SEAL who goes undercover as a bouncer to bring justice to a small Vermont town that’s under the thumb of a ruthless arms dealer, while occasionally taking time from awkward fighting for some awkward romancing of none other than Michelle Pfeiffer(’s sister). Although it was never released in the U.S., instead going direct to the heartland of Russia, Radical Jack has since become a favorite of RiffTrax and other bad cinema connoisseurs. Fortunately, Cyrus quickly rebounded with supporting roles in and his daughter’s life, and has had a successful run in basic-cable series like Doc and Still The King that don’t require anyone to pretend to be intimidated by him. [Sean O’Neal]

Most pop-star vehicles could just as easily serve as biopics. The plots usually allow the artists to play some version of themselves, like, say, an aspiring singer. But the familiar ground just makes it all the more disappointing when the talent in question can’t pull it off. In 2005’s Popstar, Aaron Carter, solo artist and brother of Backstreet Boy Nick, played a kid named J.D. McQueen who was already at the top of the music game (hence the title). For all his hit singles, J.D. struggles with math, which threatens his career. That’s right—his mom (Tracy Scoggins) is prepared to ground him, which would force him to drop out touring. Otherwise, J.D. lives a charmed life; he even finds an attractive math tutor (Alana Austin). That luck didn’t extend to Carter’s performance, which proved he was best encountered in the three-minute doses of music videos. Carter grew up in the public eye, but the once prepossessing kid just looks clueless as he pretend-juggles school and work. His film career sputtered out not long after, though he did have a role in and Robert Patrick. [Danette Chavez]

Neil Diamond’s 1972 double live album Hot August Night was a huge hit, so his cinematic transition was perhaps inevitable; everyone who bought the album was bound to go see him in a movie to watch him perform, right? Unfortunately, Diamond made his movie debut in an ill-advised remake of 1927’s The Jazz Singer, the movie that brought “talkies” to the screen. Decades of distance did little to make the story of a man breaking from his family to become a star relatable, and a nod to the original by inserting a scene of Diamond in blackface probably doomed the movie outright. The Jazz Singer tried to heighten the film’s acting pedigree by casting Laurence Olivier as Diamond’s disgruntled father, but the singer’s meager acting skills just stood out more next to the man many consider the greatest actor of all time. Still, The Jazz Singer’s songs were noteworthy, including “Hello Again,” “Love On The Rocks,” and the more-pertinent-than-ever “America,” leading The Jazz Singer to be not as big of a flop as it probably would have been otherwise. Diamond wound up with the dubious distinction of being nominated for a Golden Globe and a Razzie for the same movie. [Gwen Ihnat]

Cool As Ice stands as a harried attempt to squeeze whatever profits remained in the Vanilla Ice game following the release of the thoroughly unnecessary concert album Extremely Live. Playing motorcycle-riding drifter/rapper Johnny Van Owen, the film finds Ice and his touring crew/fellow drifters breaking down in the hometown of comely goody-two-shoes Kathy Winslow (Kristin Minter). In the tradition of all great romances, Johnny makes the first move by pulling a motorcycle trick that causes Kathy to be thrown from a horse. From there, this veritable Romeo and Juliet (but, alas, they make a sheath for no happy dagger) weather the disdain of Kathy’s father (a post-Family Ties Michael Gross), the fury of Kathy’s preppy boyfriend (John Newton, object of the film’s most memorable line: “Words of wisdom: Drop that zero and get with the hero”), and the ill intentions of the crooked cops attempting to off Mr. Winslow. Like Ice himself circa 1991, Cool As Ice is totally devoid of substance, but it has a hell of a look, with all sorts of then au-courant music-video and TV-commercial trickery from director David Kellogg (who directed Michaels Jackson and Jordan in “Jam”) and cinematographer Janusz Kaminski (who’d later win Oscars for shooting Schindler’s List and Saving Private Ryan). If it weren’t for the constant scenes of Ice doing what he was known for—dancing well and rapping adequately—it’d almost be worth watching with the sound turned off. Almost. [Erik Adams]

A fictional character whose concerts are Grand Guignol spectacles, Alice Cooper, a.k.a. Vincent Furnier, would seem a natural fit for movie stardom. In small doses, that’s certainly the case: Cooper’s gothic presence has enlivened films both scary (Prince Of Darkness, Freddy’s Dead) and funny (Wayne’s World), but typically it’s little more than a cameo—and most often, just playing himself. The sole exception is 1984’s Monster Dog, from Italian schlock-meister Claudio Fragasso, which Cooper starred in during a personal nadir of divorce, being dropped by his label, and struggling with substance abuse. As a form of art therapy, Monster Dog deserves credit for keeping Cooper tethered amid one of the worst periods of his life. But as a film, it rivals Fragasso’s own Troll 2 in being unwatchable outside of anything but fan devotion or morbid fascination. Cooper plays “Vince Raven,” an Alice Cooper-like rock star who returns to his childhood home to shoot a music video, where the crew is terrorized by a murderous pack of wild dogs and Raven must confront a dark family secret involving a werewolf—or, in Fragasso’s imaginative parlance, “monster dog.” And while Cooper does perform two original songs, all of his dialogue was overdubbed, making him little more than a cipher in a film he’d rather not be seen in anyway. [Sean O’Neal]

After she charmed audiences inand The Best Little Whorehouse In Texas, putting country-music legend Dolly Parton in her own rom-com probably seemed like a good idea. The decision to pair her with Sylvester Stallone was less wise, but there was probably an ”opposites attract” pitch in there somewhere. Rhinestone falls back into the “I’m gonna kiss the next guy I see” or “I can make the next girl who walks in here beautiful” trope: Here Parton’s Jake makes a bet that she can turn the next person who crosses her path into a country star, or else she has to sleep with skeevy manager Ron Leibman (the ’80s: not the most feminist decade). That person, of course, tuns out to be Stallone’s New York cabbie. At least the movie puts Dolly on stage to sing a lot; unfortunately some of those times, Stallone is right up there with her, probably hoping that his sequined fringed jumpsuit will distract everyone from his helpless warbling. Parton’s hair is so ginormous throughout that in their kissing scene, all you can see is her head. But Dolly’s no dummy: For her next screen outing she went right back to a successful ensemble with Steel Magnolias. [Gwen Ihnat]

An innovator of punk’s spiked-hair, safety-pinned, spray-paint aesthetic, Richard Hell cut an especially iconic figure in a scene defined by its iconography. And with his tall, lean figure and classically handsome features, Hell was a natural choice to be the face of punk when it broke into movies as well. Unfortunately, his acting never quite matched the charisma he brought to the stage, even when playing the most loosely fictionalized version of himself, as in Ulli Lommel’s Blank Generation. Named for one of Hell’s songs—and featuring actual CBGB’s performances from his band, The Voidoids—the film’s relationship to punk more or less ends there. Instead, Hell’s rock singer alter ego wanders aimlessly through an airless Godard pastiche, squabbling periodically with a French journalist with whom he’s entered a tempestuous relationship (Carole Bouquet), until Andy Warhol finally wanders in for a brief, embarrassed cameo. “” Hell would later say, and although he would try acting again—including playing almost the exact same part in Smithereens, from Desperately Seeking Susan director Susan Seidelman—he quickly, wisely recognized that acting just wasn’t for him. [Sean O’Neal]