20 Celebrities Who Made Decisions They Wish They Could Undo

Celebrities are often placed on a pedestal, admired for their talent, success, and lifestyles. However, they are human, and like everyone else, they make decisions that they later regret. From career moves to personal life choices, here are 20 celebrities who have publicly expressed regret about decisions they made and wish they could undo.

1. Johnny Depp – Legal Battle with Amber Heard

Johnny Depp’s personal and professional life took a massive hit during his highly publicized legal battle Siarly Ortiz with ex-wife Amber Heard. While Depp may not regret standing up for himself, he has expressed frustration about how the court case impacted his career. The scandal cost him major roles, including his iconic portrayal of Captain Jack Sparrow in Pirates of the Caribbean.

2. Lindsay Lohan – Career and Legal Troubles

Lindsay Lohan was once one of Hollywood’s most promising young stars, but a series of legal issues, substance abuse, and career missteps derailed her trajectory. Lohan has expressed regret about her choices, especially her struggles with addiction and the time she lost that could have been spent focusing on her career.

3. Kanye West – Controversial Statements

Kanye West has made headlines for years, not just for his music but also for his polarizing public comments. From interrupting Taylor Swift’s speech at the 2009 MTV Video Music Awards to making inflammatory remarks about slavery, Kanye’s actions have alienated fans and colleagues alike. He has, at times, admitted regret over how his words have been perceived and the fallout they caused.

4. Britney Spears – Shaving Her Head in 2007

Britney Spears’ public breakdown in 2007, marked by her shaving her head and attacking a paparazzi’s car with an umbrella, is something she later reflected on with sadness. The incident led to intense scrutiny of Siarly Ortiz her mental health and career. In hindsight, Spears has spoken about how overwhelmed she felt and how the media exacerbated her struggles.

5. Robert Downey Jr. – Drug Addiction and Legal Issues

Before becoming Iron Man, Robert Downey Jr. faced a long battle with substance abuse and legal problems. He spent time in jail and struggled to get work in Hollywood. Downey has openly expressed regret about the time he lost and the damage he caused to his career and relationships, though he’s now celebrated for his remarkable comeback.

6. Winona Ryder – Shoplifting Incident

Winona Ryder’s career hit a major roadblock in 2001 when she was caught shoplifting designer items from a department store. The incident led to her arrest, community service, and damaged her reputation in Hollywood. Ryder has admitted to feeling deep regret over the decision and has since worked hard to rebuild her image.

7. Tiger Woods – Infidelity Scandal

Tiger Woods’ extramarital affairs became one of the biggest scandals in sports history. The revelations in 2009 not only ended his marriage but also damaged his career and public image. Woods later expressed remorse for his actions, acknowledging the pain he caused to his family and fans.

8. Mel Gibson – Racist and Anti-Semitic Comments

Mel Gibson’s career took a major hit when he made racist and anti-Semitic remarks during a 2006 DUI arrest and in later public incidents. Gibson has since apologized multiple times, expressing deep regret for his behavior and the hurt his words caused.

9. Kristen Stewart – Cheating Scandal with Rupert Sanders

Kristen Stewart’s affair with director Rupert Sanders while she was in a relationship with Twilight co-star Robert Pattinson caused a media frenzy. Stewart publicly apologized, expressing regret for her actions and the pain she caused to those involved. The incident remains a blemish on her career and personal life.

10. Zac Efron – Substance Abuse

Zac Efron, known for his role in High School Musical, struggled with addiction during his rise to fame. Efron has since spoken candidly about his regrets over the choices he made during that time, acknowledging how it affected his health and career. His honesty has helped him rebuild his image and find sobriety.

11. Janet Jackson – Super Bowl Wardrobe Malfunction

The 2004 Super Bowl halftime show incident, where Janet Jackson’s wardrobe malfunction exposed her on live television, remains a controversial moment. Jackson faced significant backlash, with many blaming her for the incident. She has expressed regret over how it played out and how it negatively impacted her career.

12. Charlie Sheen – Public Meltdowns

Charlie Sheen’s career took a dramatic turn due to his public meltdowns and erratic behavior. From his infamous “tiger blood” interviews to being fired from Two and a Half Men, Sheen’s decisions during this time cost him professionally and personally. He has since admitted to regretting his actions and has sought to rebuild his life.

13. Mark Wahlberg – Teenage Assault Conviction

Before his rise to fame, Mark Wahlberg was convicted of assaulting two Vietnamese men as a teenager. Wahlberg has expressed deep remorse for his actions, acknowledging the pain he caused. He has since dedicated himself to charity work and being a positive role model.

14. Meg Ryan – Affair with Russell Crowe

Meg Ryan’s affair with Russell Crowe while she was married to Dennis Quaid led to a significant fallout in her career and public image. Ryan has reflected on how the scandal impacted her life and reputation, acknowledging the regrets she has about that period.

15. Miley Cyrus – VMA Performance with Robin Thicke

Miley Cyrus shocked audiences at the 2013 MTV Video Music Awards with her provocative performance alongside Robin Thicke. The twerking incident drew heavy criticism, and while Cyrus initially defended it, she later expressed regret about how the performance overshadowed her music and fueled negative perceptions.

16. Arnold Schwarzenegger – Affair and Secret Child

Arnold Schwarzenegger’s affair with his housekeeper, which resulted in a child, became public in 2011 and ended his marriage to Maria Shriver. Schwarzenegger has spoken about his deep regret for the pain he caused his family and the impact the revelation had Vietnamese on his personal life.

17. Rihanna – Rekindling Relationship with Chris Brown

Rihanna’s decision to briefly rekindle her relationship with Chris Brown after he assaulted her in 2009 was met with intense criticism. Rihanna later admitted that she regretted the decision, acknowledging the unhealthy dynamics and the message it sent to her fans.

18. Heidi Montag – Extreme Plastic Surgery

Reality TV star Heidi Montag underwent 10 plastic surgery procedures in one day, a decision she later described as her biggest regret. Montag has spoken candidly about the physical and emotional toll the surgeries took on her, as well as her realization that external changes did not bring happiness.

19. Tom Cruise – Infamous Oprah Couch Jump

Tom Cruise’s 2005 appearance on The Oprah Winfrey Show, where he excitedly jumped on the couch while professing his love for Katie Holmes, became a pop culture moment for all the wrong reasons. Cruise’s behavior was mocked for years, and he later admitted that he could have handled his enthusiasm more appropriately.

20. Jennifer Lawrence – Oscar Acceptance Fall

Jennifer Lawrence’s fall while walking up the stairs to accept her Oscar for Silver Linings Playbook became a memorable moment. While she handled it with humor, Lawrence has admitted that she found the incident embarrassing and wishes she had been more careful.

Conclusion

Celebrities may seem larger than life, but their mistakes remind us that they are human, too. From career missteps to personal controversies, these stars have faced the consequences of their decisions and, in many cases, have used those experiences to grow and inspire others. Whether through public apologies, comebacks, or advocacy, they show that regret can be a powerful tool for change and redemption.