Hollywood is full of talented people who never quite made it to the top. The difference between a star and a superstar is rarely raw ability. It is almost always a single bold decision made at exactly the right time with exactly the right instinct.
Some bet on themselves when the industry told them not to. Others walked away from comfort to chase something harder and more honest. Every person on this list made a move that the rest of the room did not see coming. Here is what they did and why it worked.
Rihanna stopped releasing music and became a billionaire
Rihanna had not released a studio album since Anti in 2016 when she made the move that changed her life entirely. Rather than rush a follow-up, she launched Fenty Beauty in September 2017 as a 50-50 joint venture with LVMH’s Kendo beauty incubator. The brand launched with 40 foundation shades at a time when most prestige lines offered 12 to 15. It generated an estimated $100 million in its first 40 days and exceeded $570 million in annual revenue by 2018.
Forbes valued Fenty Beauty at $2.8 billion as of 2021, making her 50 percent stake worth approximately $1.4 billion and putting her on the Forbes billionaires list. Her entire 20-year music career, by comparison, generated an estimated $100 to $200 million in total earnings. The decision to build a brand instead of an album proved to be the most financially consequential move any pop star had ever made. Seven years of music silence turned out to be the best career move she ever did not play a single note for.
Zendaya left Disney for the darkest role she could find
Zendaya spent eight years as a Disney Channel star on Shake It Up from 2010 to 2013 and K.C. Undercover from 2015 to 2018. When she left the network, show creator Sam Levinson offered her the lead role of Rue Bennett in HBO’s Euphoria, a raw drama about a teenager battling drug addiction. Industry observers questioned whether a Disney child star could carry a show that graphic and emotionally demanding. She did it anyway.
Euphoria premiered in June 2019 and Zendaya won the Primetime Emmy Award for Outstanding Lead Actress in a Drama Series in 2020 at age 24, becoming the youngest person ever to win the category according to Guinness World Records. She won it again at the 74th Emmy Awards in 2022, becoming the youngest two-time acting winner in Emmy history and the first Black woman to win the Lead Actress in a Drama category twice. Leaving Disney for the hardest possible material was exactly the move her career needed most.
Kendrick Lamar chose craft over constant output
In an era when streaming rewards volume above all else, Kendrick Lamar released just one studio album between 2017 and 2022, a period when most of his peers were releasing music every few months to stay relevant. He signed with pgLang in 2020, a company he co-founded with Dave Free, and refused to chase trends or flood the market. In 2018 he became the first musician outside of classical and jazz genres to receive the Pulitzer Prize for Music for his album DAMN., confirming that his strategy of depth over frequency was working at the highest possible level.
When he released the diss track Not Like Us on May 4, 2024, it debuted at number one on the Billboard Hot 100 and went on to win five Grammy Awards in February 2025 including Record of the Year, the most wins of any artist that night. It became the first diss track to reach one billion streams on Spotify. He then headlined the Super Bowl LIX halftime show on February 9, 2025, as the first solo rapper ever to headline the event. Every year of silence had been building toward the loudest moment of his career.
Margot Robbie stopped waiting and built her own studio
Margot Robbie co-founded LuckyChap Entertainment in 2014 alongside Tom Ackerley, Josey McNamara, and Sophia Kerr after growing frustrated watching female-led stories fail to get greenlit in the traditional studio system. Their first film, I, Tonya in 2017, cost $11 million to make and grossed over $53 million worldwide while earning Allison Janney an Academy Award for Best Supporting Actress. LuckyChap had proven itself before anyone in Hollywood took it fully seriously.
Then Barbie arrived in July 2023. Robbie produced and starred in the film, which grossed $1.45 billion worldwide, making it Warner Bros.’ highest-grossing film in the studio’s 100-year history and the highest-grossing film of 2023 globally. Robbie earned $50 million in salary and box office bonuses. Warner Bros. immediately signed LuckyChap to a first-look deal. She did not wait for someone to hand her the right project. She built the company that made it herself and then ran straight into the biggest hit of the year.
Miley Cyrus stopped explaining herself and won two Grammys
Miley Cyrus spent years being defined by other people’s narratives. She was a Disney child star, then a controversy magnet, then a rock experiment, then a breakup story. In 2023 she released Flowers on January 13, which she wrote herself as the opening track of her eighth studio album Endless Summer Vacation. The song debuted at number one on the Billboard Hot 100 and spent eight non-consecutive weeks at the top of the chart. She did not pitch it as a comeback. She just released it and let it speak.
At the 66th Grammy Awards on February 4, 2024, Flowers won Record of the Year and Best Pop Solo Performance. They were her first two Grammy wins after 20 years in the music industry and only two prior nominations for her own work. She told W magazine she had spent years asking the industry where her recognition was. The answer turned out to be at the end of the decade she spent refusing to let anyone else write her story for her. Flowers proved that the best career move is sometimes simply trusting what you already know how to do.
Ryan Reynolds turned self-deprecation into a business model
Ryan Reynolds bought a stake in Aviation American Gin in 2018 and became its creative director rather than just its spokesperson. He rebuilt the brand’s entire marketing strategy around his natural voice, mocking traditional advertising while starring in it. Diageo acquired Aviation Gin for $610 million in August 2020. Reynolds also acquired a 25 percent stake in Mint Mobile in 2019 and applied the same approach, letting genuine personality replace polished corporate messaging. T-Mobile acquired Mint Mobile for $1.35 billion in 2023.
He and Rob McElhenney purchased Welsh soccer club Wrexham AFC for $2.5 million in November 2020. The FX and Hulu docuseries Welcome to Wrexham turned the purchase into a global sports storytelling phenomenon and helped the club win multiple promotions through the Football League pyramid. Reynolds never positioned himself as an expert in any of the industries he entered. He positioned himself as a fan. That turned out to be far more commercially powerful than pretending to be anything else.
Cillian Murphy said yes to the same director for 20 years
Cillian Murphy worked with director Christopher Nolan across Batman Begins in 2005, The Prestige in 2006, Inception in 2010, and Dunkirk in 2017, always in supporting or ensemble roles. He never pushed for the lead. He never publicly lobbied for more screen time. He simply delivered every time Nolan called and trusted that the relationship would eventually produce something bigger than either of them could manufacture on demand. He built loyalty in a business that usually rewards impatience.
When Nolan finally placed him at the center of Oppenheimer in 2023, Murphy played J. Robert Oppenheimer in a film that grossed nearly $1 billion worldwide, received 13 Academy Award nominations, and won seven Oscars including Best Picture. Murphy won the Academy Award for Best Actor at the 96th Oscars on March 10, 2024, his first-ever nomination and first win. He became the first Irish-born actor to win that category. Twenty years of patient, precise work paid off in a single role that the entire world watched.
Beyoncé made a country album and won every award it had
Beyoncé had already redefined R&B, pop, and dance music across seven studio albums and a stadium tour when she released Cowboy Carter in March 2024. The album was a full country and Americana record, a genre that had historically kept Black artists on its margins. She submitted it to the Country Music Association before it was even finished and later pulled it after it was not acknowledged. She released it anyway and debuted at number one on the Billboard 200.
Cowboy Carter won the Grammy Award for Album of the Year at the 67th Grammy Awards in February 2025, a prize that had eluded her for her entire career despite six previous Album of the Year nominations. It also won Best Country Album and Best Country Solo Performance. The Cowboy Carter Tour that followed became the highest-grossing country music tour in history at over $407 million. She did not ask country music for permission. She entered the genre on her own terms and rewrote its history on the way through.
Sabrina Carpenter wrote a joke that became the song of the year
Sabrina Carpenter spent a decade on Disney Channel and in the pop industry’s mid-tier before her 2022 album Emails I Can’t Send began turning industry heads. Rather than chase the serious prestige sound that awards voters typically reward, she leaned fully into wit, wordplay, and romantic comedy pop on her 2024 album Short n’ Sweet. Espresso, the lead single she wrote with Steph Jones, Amy Allen, and producer Julian Bunetta, went viral on TikTok in April 2024 and peaked at number three on the Billboard Hot 100 in the United States.
Short n’ Sweet debuted at number one on the Billboard 200 on September 6, 2024. At the 67th Grammy Awards in February 2025, Carpenter won Best Pop Vocal Album for Short n’ Sweet and Best Pop Solo Performance for Espresso, her first two Grammy wins. She also performed at the ceremony and was named an Apple Music Artist of the Year for 2024. The move that changed everything for her was refusing to make music that sounded more important than the music she actually loved making. Staying specific paid off far more than chasing prestige ever would have.
Reese Witherspoon got tired of waiting and built a $900 million company
By 2011 Reese Witherspoon had spent two decades inside Hollywood and had grown frustrated with the scripts landing on her desk. She told Harvard Business School’s Founder Mindset podcast that a project built around a man with two women simply vying for his affection pushed her over the edge entirely. She called her agent and refused the audition. Then she decided that if the stories she wanted to tell were not being made, she would make them herself. She co-founded Hello Sunshine in 2016 with Strand Equity’s Seth Rodsky and AT&T’s Otter Media with a single mission: put women at the center of every story.
Hello Sunshine produced Big Little Lies for HBO, Little Fires Everywhere for Hulu, and The Morning Show for Apple TV Plus in rapid succession, all starring Witherspoon and all generating critical and commercial success. In August 2021 she sold a majority stake to a Blackstone-backed media venture led by former Disney executives Kevin Mayer and Tom Staggs in a deal that valued Hello Sunshine at $900 million. Witherspoon retained significant equity and a board seat. She told Fortune in 2026 that she hoped other people would see the sale and think they could build the next Hello Sunshine. An actress who had been handed the wrong parts for 20 years simply stopped waiting and built the company that made the right ones herself.
Featured Image: Photo by Jørund Føreland Pedersen on Wikimedia Commons
