Best And Worst Celebrity Career Moves
When part of your job is marketing yourself, you have to be wary about which moves you make to reach a larger audience. Is there a certain look you want to portray? Maybe you only take projects that start with the letter “A”. Who knows. Either way, you have to be savvy when deciding which direction you want your career to go. For most of us, that depends on the office we want to be in. For those in the entertainment industry, someone’s next project could always be a make-it-or-break-it type of situation. Take a gander at some of the best (and worst) decisions stars have made! Some of these helped them make a great career. Others…well…at least people are still talking about them!
BEST: Margot Robbie, The Wolf of Wall Street
If The Wolf of Wall Street taught us anything it’s that you don’t ever go into business with Leonardo DiCaprio. You probably should avoid penny stocks too, but let’s focus on the big things. Despite what you see in the film, the stars attached to this project all seemed to make some great choices.
Due to the massive success of the movie, the cast all seemed to get some big bumps in their careers. Take Margot Robbie for example. This powerhouse entertainer went from starring in soap operas to gracing the silver screen! Not only that, but she completely stole the show in most of her scenes, too!
WORST: George Lazenby, Leaving James Bond
Once you reach a certain level of fame, it’s pretty common to start receiving a lot of movie deals. Stars who work hard are able to be more discerning later in their careers. That comes with success, folks. When you’re deciding which major picture to be in next, sometimes you have to listen to the people around you.
That doesn’t always mean they’re going to give the best advice. George Lazenby was at the top of his game when received the offer of a lifetime. He was given the chance to star as James Bond in seven movies! Why’d it never happen? He listened to his agent who said James Bond was only a fad!
BEST: Benedict Cumberbatch, Sherlock
He’s dreamy. He’s successful. He’s the most celebrated detective in the history of time. Benedict Cumberbatch can seem to do no wrong. Whatever mantle this guy takes up instantly becomes a classic. While he has a lot of great titles to his name, one in particular jettisoned him to new heights in the world of stardom.
After securing the chance to be the next Sherlock Holmes, Cumberbatch’s phone began to blow up! His ability to revive the brand and deliver it to a new audience opened a lot of doors for him in the industry. Since Sherlock, the actor has gone on to star in even bigger projects and shows no signs of slowing down!
WORST: David Caruso, Leaving NYPD Blue
Humans are interesting creatures. Even when things are going really well for us, we’ll ruin it all by shaking things up. Even when the best option is to stay put and keep doing what you’re doing, some people just can’t help but mess it all up by trying something new that may not pan out. That’s basically what happened to David Caruso.
He had a pretty sweet gig on NYPD Blue. All he had to do was keep being himself and he would make bank for the rest of his career. Of course, since people are always looking for new adventures, he tried his hand at a couple of flicks. Unfortunately, they didn’t fare nearly as well as his stint on Blue!
BEST: Florence Pugh, Little Women
Sometimes all it takes is that one special film to catapult someone into a completely new realm of success. Florence Pugh, when she’s not dominating the red carpet, is a chameleon of an actor who doesn’t get nearly enough credit. After breaking through the ceiling of the indie movie industry, she’s been on a path to superstardom that few get to tread.
After being the biggest star in Little Women and Midsommar, Pugh has traveled the multiverse. She’s starred in the Marvel franchise and has grossed top-billing in a variety of others! She’s probably due to take over the world at any moment given how much drive and success she’s had.
WORST: Katie Holmes, Leaving The Dark Knight
Who doesn’t want to move to Gotham? Okay, maybe not the actual city, but being on the set of a Batman film must be pretty cool. The opportunity to star in a successful Batman film can change people’s lives. Even big stars can experience a huge bump in their career if they play their cards right. Cristopher Nolan redefined Gotham for the new generation and all eyes were on the cast.
Katie Holmes played the brilliant and lovely Rachel Dawes in the first film. Despite doing a great job, she felt one appearance was enough! When the second installment came out, Maggie Gyllenhaal got to fill in. Why? Holmes said she had had enough and wanted to do other films!
BEST: Zendaya, Shake It Up
You can’t so much as walk down the street in Hollywood these days without seeing some sort of billboard or poster featuring Zendaya. Not only is she one of the best characters on the hit series Euphoria, but she’s breaking molds across the industry and making it extremely hard for anyone to overlook her ability to shine. Most people probably wouldn’t have given her a second thought if it weren’t thanks to Disney!
After working in music for a while, Zendaya starred in the hit Disney show Shake It Up. That platform helped springboard Zendaya to greater heights and even more exclusive and high-budget projects! It’s hard to keep your career from blowing up when you’re one of the most recognizable faces in the industry.
WORST: Katherine Heigl, Knocked Up
When it comes to being in the movies, part of your job has nothing to do with filming at all! Sometimes you just have to do a few interviews and say nice things about people. If you can’t manage that, you may just shoot your career in the foot! Katherine Heigl, an incredible actor, hasn’t been seen as much as some of her other co-stars in recent years.
While she’s certainly around and thriving, some think her career took a hit after Knocked Up. Heigl said some shady things about the director in an interview after filming. This was taken as a sign that she’s probably a bit trickier to work with than originally thought.
BEST: Leonardo DiCaprio, Titanic
It’s nearly impossible to discuss the best and worst career trajectories without mentioning Leonardo DiCaprio. This guy’s adventures in Hollywood could be their own Oscar-winning movie. Despite having a few big names under his belt by the time Titanic came out, it wasn’t until this movie that people started to pay him any serious attention. This kid’s delivery and ultimate sacrifice should have been an automatic win at the Oscars that year.
Instead, an underdog story was born that took years of hard work to complete. Thankfully, DiCaprio eventually gets his award. To earn it, he delivered great performance after great performance! None of it would have mattered if it weren’t for Jack Dawson.
WORST: Terrence Howard, Turning Down Iron Man II
You don’t just haggle at the local swap meets. Once you’ve reached a level of stardom, you can even negotiate your own movie contracts! Just like with any other job, making sure you’re getting treated fairly and paid well is super important. Of course, most people tend to forget that negotiations might cause you to lose the role.
If you’re too tough to land a deal with, an employer (or studio) will just pass you over for someone else. Terrence Howard learned this the hard way when he lost his negotiations to star in Iron Man II! He made the same mistake for the third film as well as the second Avengers movie!
BEST: Pete Davidson, Trainwreck
The world of comedy is fraught with competition, backstabbing, and drama. It’s a wonder anyone finds success in it, let alone makes it out alive or with their sanity intact. Pete Davidson not only survived the comedy world but came out on top in a short amount of time! While you can work hard for years, sometimes all you need to make it big is one shot at a big project.
Davidson’s quick wit and unique delivery landed him a small role in the film Trainwreck! This comedy set in the magazine industry allowed a larger audience a glimpse at what Pete would eventually be doing. His small performance was enough to get him an audition for SNL!
WORST: Dougray Scott, Mission Impossible II
Show of hands, who here knows who Dougray Scott is? This isn’t some guy that happens to have two first names spliced together. He’s a serious actor with some great accomplishments on his resume! More people would probably recognize him if he hadn’t passed up on starring as Wolverine. Scott was approached to take on the mantle of everyone’s favorite fast-healing mutant.
Due to the filming schedule of another movie he was in (Mission Impossible II), Scott passed up on the offer. We get it, things happen. Not everyone could see that this was the role of a lifetime. However, since he passed, the role went to a somewhat known actor and singer by the name of Hugh Jackman!
BEST: Bill Hader, Improv
Not every actor and comedy legend comes about their success in the same way. You don’t always have to be pounding the pavement in audition after audition to make it big. Sometimes all it takes is a little guts, the right connections, and an understanding of improv. Before he became a household comedy name, Bill Hader was just another improv artist trying to make it big. During a show, a couple of friends of his castmate thought Hader had some pretty funny chops.
Those friends turned out to be Nick Offerman and Megan Mullaly! The two veteran actors saw something in Hader and thought he would be a good addition to SNL. After a couple of calls, Hader was auditioning for Lorne Michaels himself. Then came the movies, the fame, the riches, and everything else.
WORST: Matthew Broderick, Godzilla
Even when you’re not doing the biggest and best movies, sometimes a star is content with just being a star. Matthew Broderick is an accomplished actor who started out with his breakout role in Ferris Bueller’s Day Off. Broderick was HUGE in the late 90s and early 00s. His career had so much upward trajectory nearly anything he did was a smash hit.
Then Godzilla and Inspector Gadget happened. One bad film isn’t enough to hurt a superstar’s career that badly. Two though? That began a pattern where Broderick saw himself getting fewer and fewer smash hits. Someone needs to talk to their agent…or get a new one.
BEST: Robert Pattinson, Good Time
Even when you’re involved in some of the biggest projects on the planet, it’s not enough to get your name out there to people. Sometimes, you need to think a bit more indie to climb the ranks. Millions of people know Robert Pattinson from Harry Potter and Twilight. While those are great things to have on a resume, it’s his work in Good Time that pushed him into the spotlight.
Pattinson’s role as the quick-thinking and empathetic bank robber completely changed how people saw him! Sure, he was a great actor in the other movies. But this role was something extraordinary!
WORST: Halle Berry, Catwoman
This is a controversial one since some of us at the office LOVED Halle Berry’s Catwoman. It was a fun and independent story that reinvented Catwoman’s origin story outside of Gotham. But not everyone loved it. In fact, it was so poorly received that it altered Halle Berry’s entire career trajectory. Needless to say, this wasn’t the best career choice.
Prior to becoming a cat-eared vigilante, Berry’s name was everywhere and always tied to the most interesting films. After she played along and accepted a Razzie for the film, it appears that she’s been a bit more selective with the movies she stars in. That’s always a good decision!
BEST: Jodie Comer, Killing Eve
It’s always dynamite seeing a television star cross over to feature films and crush it. Jodie Comer was no stranger to performing. She was a mainstay in some incredible television shows. One of her best, and arguably the one that catapulted her career forward, was Killing Eve. This four-season spy thriller showed everyone her range and acting abilities.
Once Killing Eve took off, it wasn’t long before Comer was starring alongside Ryan Reynolds in Free Guy! Thanks to the show, she’s not only dominated television, but her career in movies seems to be secure as well. Maybe she’ll go for an EGOT!
WORST: Gerard Butler, P.S. I Love You
Typecasting is never a good thing. A good actor should be able to showcase range and versatility and secure many different types of roles. Even when they can’t, letting them do what they do best is usually good for everyone involved. Unfortunately, to figure out where your limits are, you gotta make a few mistakes. Gerard Butler was easily in the top 300 list of great action stars.
After his abs and thighs made him a hit in 300, he set his sights on other genres. The excitement from his record-smashing role didn’t carry over to P.S. I Love You. It was great to see Butler excel in the role, but fans couldn’t see past his action image enough to give it a chance. Diversifying wasn’t the best choice in this case.
BEST: Meryl Streep, Mamma Mia!
Almost everything Meryl Streep touches turns into cinema gold, becomes history, and is instantly iconic. There’s something about her ability to completely transform into any role that mesmerizes people. Despite always looking the same, she plays different people effortlessly. Throughout her fifty-year career, she’s won over 200 awards! At seventy-three, and still going strong, there’s no end to Streep’s reign in Hollywood.
Any of her films could be labeled a career milestone. However, seeing her execute complex choreography, sing, and still steal the scene with jokes in Mama Mia! was next-level. It’s hard to think how she could top that, but every film proves it’s possible without taking away the perfection that was her previous role.
WORST: Chloe Sevigny, Brown Bunny
Some of the most interesting and controversial movies aren’t intended for a mass audience. Art films often use extreme or complicated imagery to tell a deeper story. Given their sometimes graphic nature, not many are well-received by the general public. At the 2003 Canne Film Festival, Chloe Sevigny learned this when her raw and unedited fellatio performance was shown at the end of Brown Bunny.
While everyone was in character, and the scene was part of the script, people weren’t happy. It didn’t matter to them that this was consensual and part of something bigger. The sight of seeing the star perform such an act as part of a major feature film was enough to turn her biggest fans into her harshest critics.
BEST: Cheryl Crow, “All I Wanna Do”
Movie and television stars aren’t the only ones who make career-defining choices. Singers have been exploding onto the scene and changing the cultural landscape for even longer! Take Cheryl Crow for example. As soon as “All I Wanna Do” hit the airwaves, millions of people were hooked. Crow started out singing along with tracks of other stars, and she became one of them almost overnight!
Since the release of “All I Wanna Do”, her career has been shining brightly across streaming platforms and radios without stopping. Her entire discography marks a shining moment in her career. Crow’s influence on music didn’t just inspire other pop and country stars, it also provided a soundtrack to generations of fans for years to come.
WORST: Jennifer Beals, Post Flashdance Career
Just because you make an unforgettable and cult-classic film doesn’t mean you’ll stay a star forever. Flashdance has a rabid and ever-growing community of fans. Jennifer Beals took that script and spun it into gold. After it came out you’d think she would be starring in countless other films! Instead, she decided to pursue a different career altogether. Beals enrolled at Yale and graduated with a degree in literature.
It may seem odd, but it makes sense. She was already enrolled while filming Flashdance. If anything, the film distracted her from finishing her studies on time! For her acting career it wasn’t great, but for her academic one? You could do a lot worse than Yale.
BEST: Emma Watson, The Perks of Being a Wallflower and Others
Even if you’re remembered for a certain movie (or eight), using that fame to springboard a larger career can be a smart move. Emma Watson proved this and showed everyone how it was done after filming Harry Potter. The actor and activist went on to star in some fantastic films outside of the magical realm. She also became an advocate and ambassador for women at the United Nations!
Watson hasn’t shied away from her acting past when performing her humanitarian duties. In fact, she’s used her platform and entertainment fame to help reach out to millions of people. When she’s not making the world a better place she’s still keeping her name fresh in Hollywood. She’s trying to better the world while still finding time to become a literal Disney Princess!
WORST: Nicolas Cage, The Matrix, Dumb & Dumber, And Others
Who doesn’t know who Nicolas Cage is? He’s stolen the Declaration of Independence, became a motorcycle-riding chain-wielding demon, and starred as an animated Spider-Man. Despite his full and fantastic career, Cage could have been a lot bigger. Over the years, multiple big-name projects came across his desk. Whether it was his agent or himself, most of them were passed up on. We’re talking HUGE movies, like The Lord of the Rings franchise, Dumb & Dumber, and The Matrix!
Even just one of those could have helped pad his career from a slew of bad roles and investments. After several less-than-stellar movies, Nicolas Cage has mostly stepped away from bigger studio films. That’s a shame because his cult following is pretty impressive and he has an unmistakable style of acting that audiences seem to love.
BEST: Adam Driver, Girls
One role can change everything. How many people can say they went from being a recurring secondary character on a comedy show to ruling the entire galaxy? The only person we can think of is Adam Driver. Driver had been acting in Hollywood for a while prior to being on Girls, but his performance as Adam Sackler attracted some pretty powerful fans.
The way he allowed himself to let go, while still maintaining control of Sackler’s frantic life caught the eye of J. J. Abrams. After that, it was space operas, perfume ads, and hosting SNL. The Force is most definitely strong with this one.
WORST: Renee Zellweger, Plastic Surgery
When you have it all and have done it all, what are you supposed to do with your money? Once you reach the top of the game, how do you spend your time not maintaining your place at the top? Some stars take to farming. Others learn woodworking. Some others prefer to focus on working on themselves. Finally having the means to achieve a look that makes you feel content with yourself can be exhilarating.
While you don’t need money to find inner peace, it helps some actors get there. After hitting it big, Renée Zellweger appeared to be showing up at more doctor’s appointments than movie premieres. Her talent has never diminished, but her face has changed so much she’s practically a new person!
BEST: Jennifer Lawrence, Winter’s Bone
Pick a Jennifer Lawrence movie and we can probably find a hundred articles claiming it’s the crown jewel of her career. Jennifer Lawrence is just one of those people who can fill any role and deliver a version of a character that can’t be found anywhere else. Whether you know her from The Hunger Games, Silver Linings Playbook, or Red Sparrow, it’s hard to see something that isn’t starring the highest-paid actress in Hollywood.
One of her underrated blockbuster hits is Winter’s Bone. It’s weird there wasn’t more buzz, because this is clearly one of her best roles. At just twenty years old, Lawrence received a Best Actress nomination at the Oscars for her performance in this coming-of-age drama! When we were twenty we were just trying to survive term papers…
WORST: Mickey Rourke, Boxing
Full-contact sports have been a part of humanity for hundreds of years. In the Colosseum, the Octagon, and the boxing ring, people love putting other people into a shape and forcing them to fight. Some actors have even tried their hand at professional boxing just to see what all the hubbub is about. While doing research for a role is good, you still need to know the risks.
Boxing stars get paid a lot because they put their physical and mental risk! After a few tours in the ring, Rourke learned this could be a potentially career-ending price. After getting his face fixed over and over again, he was beginning to become unrecognizable in the movies he starred in!
BEST: Michelle Williams, Dawson’s Creek
Living near any body of water raises property values by a certain amount. People just love being near H2O. There’s something about it that can change a person’s life in an unexpected way. In the 90s, anyone who was anyone wanted to live on or near a creek. Dawson’s Creek was definitely the preferred one, but we’d take what we could get.
Even the stars of Dawson’s Creek benefitted in weird ways! Michelle Williams somehow became the breakout star of the entire show. After appearing in the series she got major opportunities to climb the acting ladder. By the time 2011 rolled around, she was starring as Marilyn Monroe and other big names!
WORST: Chevy Chase, Leaving Saturday Night Live
Saturday Night Live has always been a Holy Grail for many comics and improv artists. If you can secure a spot on the cast list then you made it in the industry. Some of the biggest names in comedy have never had the honor to grace the stage, let alone join its ranks. One of the show’s biggest names was only on air for a couple of seasons.
Legendary comedian and actor Chevy Chase had everything going for him in the late 70s. After getting a spot on the show’s permanent cast list, Chase’s ego got the best of him. He eventually left for greener pastures and large movie deals. After some clunkers and bad decisions, the only ones laughing, in the end, were those who stayed at SNL.