Singers That Tried To Break Into Acting And Failed Miserably

It seems as though most famous people find themselves dabbling in acting at some point or another, from professional athletes to models to just about any type of celebrity that exists. This is perhaps most true for musicians, who often become actors, or vice versa — and sometimes even maintain successful careers in both music and acting for extended periods of time. Still, even with the large number of musicians who became successful actors, plus actors who became successful musicians, it is still a dicey jump to make from one career to another as it often doesn't pan out.

Arguably the best example of a musician turned actor is Will Smith, who began his career in the '80s as a rapper before transitioning to television and then Hollywood where he would go on to become one of the biggest movie stars of all time. And he's far from the only one, as Mark Wahlberg, Queen Latifah, Mandy Moore, Justin Timberlake, and Ice Cube, to name a few, have all flawlessly transitioned from singing to acting. That said, there are also a fair number that tried to follow in the footsteps of those musicians but failed, whether they weren't fortunate enough to find the right projects or they simply didn't have the chops to pull it off. A few that had rocky starts, like Mariah Carey and Beyoncé, stuck with it and eventually found their acting groove — but the ones on this list weren't so lucky.

For a time, Rob Van Winkle — better known as Vanilla Ice — was the biggest star on the planet, with his hit rap single "Ice Ice Baby" having the distinction of being the first rap song to top the Billboard charts. As uncomfortable with this fact as hip hop purists may be, "Ice Ice Baby" helped to bring rap music to a mainstream audience in a way that it hadn't achieved before. His celebrity quickly grew beyond simply being a rapper, as he would have a highly publicized relationship with Madonna, was the basis for a doll, and soon found himself in several major motion pictures.

While his actual film debut was little more than the infamous "Ninja Rap" performance in 1991's "Teenage Mutant Ninja Turtles II: The Secret of the Ooze," Ice would be the lead in his own movie later that year. The not-subtly-titled "Cool As Ice" was clearly a hastily thrown together attempt to get a Vanilla Ice movie into theaters as quickly as possible so as not to miss the small window of Ice's peak popularity. It failed in that endeavor as Ice's time as an A-list musician was already waning by then, to say nothing of how absolutely dreadful of a movie "Cool As Ice" is (and how unimpressive Ice's performance was in it). Ice would continue to do brief cameos in movies, often as himself, but any attempt at an actual acting career started and ended with "Cool As Ice." 

It's pretty easy to make the case for Carrie Underwood being the most successful "American Idol" contestant of all time, as she's sold the most albums, has the longest-running number one song, and has won the most Grammy awards of anyone who has competed on the show, winner or otherwise. The distinction is all the more impressive when you consider that Underwood isn't a mainstream pop star like Kelly Clarkson or Adam Lambert, and has racked up those milestones and accolades entirely within the spheres of country and gospel music. But Underwood hasn't succeeded in everything she's tried: her role in the 2011 movie "Soul Surfer" was the last time she attempted an acting role where she doesn't play herself or can mostly rely on her singing.

Underwood wasn't egregiously bad in the movie, but her role was called "superfluous," and didn't exactly serve to announce her arrival as an actor to keep an eye on. Other than cameos in TV shows as herself, the only acting Underwood had done previously was in a single episode of "How I Met Your Mother." Since "Soul Surfer," it's been largely the same, save for her starring role in NBC's live production of "The Sound of Music." That earned Underwood high praise for her singing and criticism for her acting, including from the real-life Von Trapp family. It seems pretty obvious which of the two she should stick with.

Jason Derulo! Try not to be shocked that the R&B artist who launched his career with the gimmick of singing his own name in his songs has played himself in most of the films and TV shows he has thus far appeared in. It's hard to completely blame him, however, as he certainly has enough charm and charisma as himself to not bother trying to be anyone else. He's even parlayed much of that talent at being appealing as himself into a successful secondary career as a TikToker. 

But Derulo has taken a few cracks at actual acting, first appearing in Episode 2 of the first season of Fox's "Lethal Weapon" TV series. His character, a boxer named Ronald Dawson, only played a small part in the story of just that one episode and was never seen again. He followed that up with a role in the 2019 film adaptation of the legendary Broadway musical "Cats," which is now a well-documented train wreck in almost every way imaginable. It certainly didn't do any favors for any of its cast who weren't already established actors. Derulo will next play music legend Ron Isley in "Spinning Gold," an upcoming biopic about influential record executive Neil Bogart, so he might yet salvage his still-fledgling acting career. Until then, it's impossible not to unsee him as a bad CG cat man.

If singers could get royalty payments any time a bar full of people drunkenly belted out one of their songs, Neil Diamond would be a billionaire by now thanks to countless alcohol-fueled "Sweet Caroline" singalongs over the decades. From his early days primarily as a songwriter for other artists in the '60s to finally finding success singing his own songs in the '70s, Diamond was one of the biggest forces in music in both decades. He remained so in the '80s and beyond as acts like UB40 and Urge Overkill covered his songs and introduced his music to whole new generations, helping to ensure his lyrics would live on well beyond his own career as a performer.

In the midst of all that, Diamond took on the then-latest in a series of adaptations of the 1925 play "The Jazz Singer" in what would be the story's fourth attempt at a screen version. Though Diamond would be nominated for a Golden Globe for his performance, he was also nominated for a Razzie, the latter of which he actually won. That tracks with what most critics said of his performance in the movie, though some blamed the script and said that Diamond did the best he could with terrible material. Either way, Diamond took the harsh criticism of his acting and the movie itself very badly, and would all but abandon acting entirely, save for appearing as himself in the 2001 comedy "Saving Silverman."

While Jessica Simpson technically began her career and rose to fame as a singer, it was her appearances on the MTV reality show "Newlyweds: Nick and Jessica" that launched her into mainstream celebrity. There are probably just as many people, if not more, who can name the brand of tuna that she mistook for chicken than can name any of her songs. That, coupled with her famous curves, are probably what kept Simpson in the limelight far longer than her music alone probably would have — because it most certainly wasn't her acting career.

While Jessica Simpson certainly had the pretty face and long legs to at least look the part of Daisy Duke for the 2005 film adaptation of "Dukes of Hazzard," she lacked the charisma of Catherine Bach, who played Daisy in the original TV series. Simpson would attempt to be the token hot girl in four more movies after "Dukes," but none of them — "Employee of the Month," "Blonde Ambition," "The Love Guru" (as herself), or "Private Valentine: Blonde and Dangerous" — would ultimately disprove the idea that she lacked the acting talents to match her physical gifts or vocal range. She finally realized that she was better suited for cameos and appearances on reality shows, which she has largely stuck to since 2008.

When a singer wins "American Idol," they are automatically committed to various obligations and projects. In the case of Kelly Clarkson, winner of the very first season of "American Idol," one such obligation was to star in the 2003 movie "From Justin to Kelly." Clarkson has since said that she knew the movie was going to be awful, yet had no choice but to star in it as it was one of the things she signed up for as an "Idol" winner. Still, just because she was stuck making a bad movie didn't necessarily mean that her acting career had to be over before it started. Her co-star, "Idol" Season 1 runner-up Justin Guarini, was able to recover from his appearance in the film and has gone on to become quite the prolific live theater actor.

Clarkson, on the other hand, didn't achieve the same results for her acting career after her inauspicious major motion picture debut — which was technically her second film, as she had actually first appeared in a small role in the little-seen gay romantic dramedy "Issues 101" the previous year. Of her three film roles post-"From Justin to Kelly," only 2020's "Trolls World Tour" got decent reviews, while all three were merely voice roles and relied mostly on Clarkson's singing chops. As for television, Clarkson popped up here and there in minor roles on various sitcoms before finally deciding in recent years that judging singing competitions and hosting talk shows were more her speed. 

Even as a musician, Gene Simmons has always had a flair for the dramatic. His band, '70s party rock icons Kiss, were as much about their personas and their stage theatrics as they were about their actual music. Adorned in elaborate face paint and decked out in costumes that made them look like armored alien warriors, Kiss didn't put on rock concerts so much as they performed a sci-fi musical stage show. Simmons was the hammiest one in the group, breathing fire, spitting blood, and frequently sticking out and flicking his absurdly long tongue to really hammer home the delightful ridiculousness of the whole thing.

Even when he's not on stage, Simmons is still a larger-than-life personality who has just as much ego in a room with a handful of people as he does in front of an adoring crowd of thousands. With all that in mind, an acting career would have seemed like a foregone conclusion. Yet in his first acting role outside of a Kiss project — 1984's sci-fi flop "Runaway" — Simmons seemed bored and completely uninterested in the whole endeavor. This would remain the case for the handful of dramatic films he would attempt in the '80s before seemingly realizing that he was only into the performance when he was performing as himself. While he technically played actual characters in a few movies here and there since then, it's clearly always just been Gene Simmons, only with a different name. 

Adam Levine, frontman of pop rock band Maroon 5, has always been a capital-S Superstar. Even before he branched out beyond just being the lead singer of a band, Levine just felt like a crossover star based on his talent, looks, and charisma alone. Some of his first attempts at acting came via various Andy Samberg-Lonely Island shorts on "Saturday Night Live," and it seemed like he might have a successful secondary career as an actor ahead of him. After a brief stint on "American Horror Story," Levine took the obvious next step and tried movies, appearing with both actors and fellow musicians in the musical rom-com "Begin Again" in 2013. 

Despite the film seeing generally favorable reviews, Levine didn't end up being much of a presence in the movie. Part of the issue was being overshadowed by far better and/or more seasoned performers — including Mark Ruffalo, Catherine Keener, and Keira Knightley — but much of it just came down to Levine himself. His performance came off stiff and he was always the least interesting thing happening in any of his scenes, neither of which you would expect from an Adam Levine performance. Levine has acted in a few more things since, but none have been of any particular note, with his charm better represented in his musical performances along with his judging stint on "The Voice." 

Christina Aguilera is good at reinventing herself every few years in order to keep her image from getting stale. And it's not just within her music career that she switches things up, as she has also done a stint as a reality show host on "The Voice" and, for a time anyway, it looked like she was going to take a swing at being a movie star. As far as potential star-making vehicles go, "Burlesque" had all the pieces in place, from a story that played to Aguilera's strengths as a singer and dancer to the legendary Cher serving as the story's aging mentor. In fact, it was Cher's first movie in seven years, so that alone was enough to garner the film some strong attention.

To Aguilera's credit, she delivers a strong performance in "Burlesque," with critics calling her "better than expected" in the role. The movie didn't light the box office on fire, although it has since earned the title of cult classic from people who appreciate its intentionally campy vibe. It nevertheless failed to ignite Aguilera's fledgling acting career: she's appeared in only two more movies since — one of which was the dreadful "Emoji Movie" — with neither giving her more than a fairly minor role. She may have the acting chops when she applies herself, but unfortunately that doesn't always a guaranteed movie star make. 

While it's not uncommon for a country singer to de-twang-ify their sound a bit in order to cross over into mainstream pop music, Garth Brooks is a rare example of a country artist who ended up become a major crossover success while still rocking his same signature country sound (not to mention his cowboy hat and boots). That is, except for a brief period in the late '90s when Garth Brooks temporarily "became" the fictitious Australian rock star Chris Gaines.

The plan was for Brooks to star in a movie called "The Lamb" as Chris Gaines, an aging rock star who was looking back at his storied musical career. Ahead of the movie, Brooks released an album called "Garth Brooks in...The Life of Chris Gaines," which was to serve as the soundtrack for the movie and also get people used to the idea of Brooks as Gaines. So committed was Brooks to inhabiting the fake Gaines that Garth Brooks hosted "Saturday Night Live" in November 1999 with musical guest Chris Gaines, never breaking character during those performances nor acknowledging that the two men were actually the same person. 

The Chris Gaines track "Right Now" saw modest radio play and the album itself would go double platinum in the U.S., but it underperformed for a Garth Brooks release and fans were largely unimpressed. As a result, "The Lamb" never ended up being made. Brooks' movie career was basically over before it began, beyond the occasional cameo.

Knowing all we now know about Britney Spears' personal life as well as the unfair pressures put upon her career by people who never had the best intentions for her, it is really hard to talk too negatively about her or that career. Still, facts are facts, and the fact is that her acting career never got off the ground — though it's probably for the best that she didn't have yet another thing to stress about and for other people to make money from on her "behalf." 

Not counting the little-seen 2001 film "Longshot" — which was little more than a barely-disguised promotional tool for NSYNC, O-Town, and other pop acts of the time — Spears' big acting debut was her top-billed role in the 2002 road trip film "Crossroads." Reviews were mostly negative, though some said that Spears did a commendable job considering her inexperience and the subpar script she had to work with. It made its money back, but for the most part, it is typically mentioned in the same conversation as other failed pop star vanity projects like "Glitter" and "Spice World." That same year, Spears also appeared as herself (though a version that was secretly a Fembot) in a fun cameo in "Austin Powers in Goldmember," and that was the lane she stayed in for future acting roles: herself or some exaggerated version of it.