16 Musical Artists Who Tried (And Failed) To Be Actors

There’s a lot of crossover in the world of entertainment. Many performers are triple, even quadruple threats, boasting talents that allow them to succeed as musicians, actors, dancers, and more. Who would have thought that Wheelchair Jimmy would become Grammy-winning artist Drake, or that today’s teens would know Will Smith as a sci-fi actor and not the genius behind PG rap hits like “Miami”?

But not everyone can bridge that gap, no matter how hard they try. These artists tried to make it on the big (and small) screens, but they weren’t successful, whether due to bad choices or just a simple lack of talent. Here’s a look at their disastrous attempts to become actors. They should have stuck to making music.

16. Usher

With his smooth voice, good looks, and serious charm, Usher is the real deal. When he rose to prominence in the late ‘90s, it was commonplace to try and get young up-and-comers into acting and music at the same time, and that’s just what he did, appearing in teen TV shows like Moesha and Sabrina the Teenage Witch and teen flicks like She’s All That and Light It Up.

Giving credit where it’s due, Usher persevered for quite some time. He even tried his hand at Broadway, appearing in Chicago. His last film, Hands of Stone, was well-received, but didn’t get much hype.

15. Jessica Simpson

Early ‘00s pop star Jessica Simpson was just becoming popular for her music when she married 98 Degrees singer Nick Lachey. The two were seemingly angling to launch acting careers with their MTV reality show, Newlyweds: Nick and Jessica. To be fair to Simpson, some people do remember her best for her “is this tuna or is this chicken?” moment on the show.

As with their marriage, her time in acting was brief, a bit of a trainwreck, and ended in the mid-‘00s. Her roles as Daisy Duke in The Dukes of Hazzard and as Kelso’s girlfriend on a few episodes of That ‘70s Show were memorable, though not really in a good way. For the last decade, Simpson has mostly been focused on her family and fashion and has only appeared on TV as herself.

14. Taylor Swift

From country singer, to pop star, to… actress? Not exactly. Taylor Swift is Grammy-winning recording artist with an impressive following. And like so many before her, she has tried her hand at acting, but unlike most, she doesn’t really seem to take it seriously.

Swift has exactly three credits in which she did not simply appear as herself: The ensemble rom-com Valentine’s Day, a vocal performance in the 2012 animated movie based on the kid’s book The Lorax, and as Rosemary in The Giver. All were small, yet fairly memorable roles in otherwise mediocre films. Maybe she’ll try again someday?

13. Lil Wayne

You definitely can’t say Lil Wayne doesn’t have talent. How many rappers, or artists of any kind really, get signed at age nine? After spending his teenage years in group Hot Boys, Lil Wayne founded his own label imprint, Young Money Entertainment, and the rest is history.

His foray into acting was, however, much shorter. Lil Wayne has few very credits, and his last film role was 2010’s Hurricane Season. But we doubt he’s sweating it — at only 35, he’s already one of the best-selling artists of all time.

12. Pink

So what, she’s not a movie star? But let’s be real: She is a rock star, in so many ways. Pink is a musical icon, and she’s proven herself to be a chart-topping performer time and time again.

But Alecia Moore (her birth name, and how she is credited for her few acting roles) probably won’t ever win an Oscar. Her last credit as Moore was in 2013’s forgettable film Thanks For Sharing. Don’t worry, Moore: We’ll keep watching you as Pink for as long as you let us.

11. Miley Cyrus

Miley Cyrus might seem like a strange choice for this list. After all, many of us know her name because of a TV show: Hannah Montana, of course. But Cyrus has since spoken out about how traumatic her experience on the show was, so it’s not really a shock that she pivoted away from acting, for the most part.

She starred in a few poorly reviewed films post-Disney Channel, including The Last Song, where she met her partner, Liam Hemsworth. Her most serious attempt to revitalize her acting career was the Woody Allen-helmed Amazon series Crisis in Six Scenes, which was a major flop. Who knows, though — she could always bounce back. We’ve seen her revamp her image more than once, so anything is possible.

10. Kanye West

We all know that Kanye West has a lot of confidence in his talent. We also have seen him on Keeping Up with the Kardashians for years now, given the family he married into. But those two things do not necessarily add up to success in acting.

There’s no doubt that the man is entrepreneurial, and he attempted to spin that into a film career. West wrote, directed, and starred in two short films, Runaway in 2010 and Cruel Summer in 2012. Both shorts were fairly well-received.

He also appeared in an uncredited cameo in Anchorman 2: The Legend Continues, and voices a parody version of himself on The Cleveland Show. But it appears as though he’s learned his lesson, and returned to music where he belongs.

9. Mariah Carey

We know singer Mariah Carey for her epic range, diva attitude, and memorable pop hits. But many of us also remember a time when she tried — and seriously failed — to become an actress.

She made her debut in the 1999 rom-com The Bachelor which you’ve likely never heard of. Then came her first starring role, in Glitter, her very own musical vehicle that flopped terrifically. She’s tried a few more times, with small parts in a few Lee Daniels projects, but generally speaking, she only appears on the big screen in cameo roles these days, playing herself.

8. Madonna

The “Material Girl” is an interesting case. From the beginning of her career, she was clearly angling to make it both as an actress and a singer. And she’s had many starring roles, from Desperately Seeking Susan to A League of Their Own.

But it quickly became clear that her talents lay exclusively in musical performances. Madonna was nominated for a number of Golden Raspberry Awards for Worst Actress, and the primary film she received acclaim for was Evita — likely because it’s a musical. She even tried her hand at directing, but her career has slowed down in recent years, so we think she’s taken the hint.

7. 50 Cent

His big break came from a track on a soundtrack (“Wanksta” on 8 Mile), so it’s not surprising that Curtis Jackson would try and make his way into the film world. After his debut album Get Rich or Die Tryin’ received much acclaim and he landed his own label, he took that title and spun it into a biopic of the same name. And it bombed.

But he didn’t give up. 50 Cent continued to appear as Jackson in numerous crime and straight-to-video action flicks over the next few years. He also has a main role on the Starz crime series Power. He has dabbled a little in comedy, but he mostly sticks to drama. So we guess he hasn’t exactly failed, but his acting career certainly isn’t what he’s known for.

6. Prince

Prince is another artist whose importance in the music industry cannot be overhyped. Prior to his death in 2016, the phenomenal performer dazzled us for decades, releasing nearly 40 studio albums and winning eight Grammy Awards. But sadly, acting wasn’t for him.

His first rock drama Purple Rain was well-received, but after directing and starring in the comedy Under the Cherry Moon, which won several Golden Raspberry Awards, he never recovered. Prince went on appear as himself a few more times, but ultimately, he was finished with the film world post-1990.

5. Keith Richards

To be fair, it doesn’t seem like Keith Richards has ever actually tried to get into acting. The Rolling Stones frontman is a profoundly skilled musician, and has no doubt made a lasting impact on the world of music.

Prior to the 21st century, Richards’s sole acting credit was as a soldier in the 1969 German film Man on Horseback. Today, some may be more familiar with him as Captain Teague from the Pirates of the Caribbean franchise, which is really more a cameo role. Aside from that, he’ll ultimately remain known as a musician.

4. Vanilla Ice

Humility is an important quality. Artists who know how to make fun of themselves often do best when transitioning to film. But honestly, did anyone think a one-hit-wonder like Vanilla Ice would actually make it as an actor?

His first attempt was Cool as Ice, a rom-com that failed spectacularly. From there, he went on to make a couple of cameos, most recently in The Ridiculous 6 as Mark Twain. At present, you can find him trying to revive his career on tours of ‘90s musicians and on shows like Dancing with the Stars. Ouch.

3. Britney Spears

In the beginning there, it seemed like Britney Spears could do no wrong. She was the sugary-sweet Southern singer with a voice to match and slightly promiscuous dance moves. And though her rough period happened later, her attempt at becoming a triple threat was sort of a dark time itself. Who doesn’t remember her personal version of Glitter, Crossroads?

The funny thing is, Spears spent a lot of time on the small screen before we even knew her name — she spent several years on The Mickey Mouse Club as a child. So maybe it wasn’t all that surprising when she tried again with guest roles on sitcoms Will & Grace and How I Met Your Mother. Fortunately, it didn’t take her (or casting directors) long to realize she only belongs on the stage.

2. Eminem

Rapper Eminem had a meteoric rise to fame in the late ‘90s and early ‘00s. With the support Dr. Dre and his no-holds-barred style, he was (and is) a force to be reckoned with. And, like so many before him, as he became bigger, he stretched his talents into the acting world.

No one can forget 8 Mile, the semi-autobiographical film he starred in in 2002. “Lose Yourself” won an Academy Award, after all. And the movie was actually a success, receiving fairly positive critical reviews. But, unlike most, Marshall Mathers knew to quit while he was ahead. Aside from occasional cameos (typically as himself), Eminem has stayed out of Hollywood. He told his story, and that’s all he had to say.

1. Kelly Clarkson

The American Idol winner and The Voice coach has maintained her initial fame over the years since she first appeared on our TV screens. Every time we’ve seen her since, it’s primarily been in a judge/musical role. But lest we forget the disaster that was From Justin to Kelly.

To capitalize on their AI fame, an absolutely terrible musical rom-com was made, starring Kelly Clarkson and the season’s runner-up, Justin Guarini. There’s not much else to say, other than that it was a major flop. It’s one of those so-bad-it’s-good flicks. Fortunately, Clarkson didn’t really try again — aside from her role on American Dreams as ‘60s pop singer Brenda Lee, she hasn’t tried to act as another person since.

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