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In 1989, Berry moved to New York City to pursue her acting ambitions. During her early time there, she ran out of money and briefly lived in a homeless shelter and a YMCA. Her situation improved by the end of that year, and she was cast in the role of model Emily Franklin in the short-lived ABC television series Living Dolls, which was shot in New York and was a spin-off of the hit series Who's the Boss?. During the taping of Living Dolls, she lapsed into a coma and was diagnosed with type 1 diabetes. After the cancellation of Living Dolls, she moved to Los Angeles.

Berry's film debut was in a small role for Spike Lee's Jungle Fever (1991), in which she played Vivian, a drug addict. That same year, Berry had her first co-starring role in Strictly Business. In 1992, Berry portrayed a career woman who falls for the lead character played by Eddie Murphy in the romantic comedy Boomerang. The following year, she caught the public's attention as a headstrong biracial slave in the TV adaptation of Queen: The Story of an American Family, based on the book by Alex Haley. Berry was in the live-action Flintstones movie playing the part of "Sharon Stone," a sultry secretary who attempts to seduce Fred Flintstone.

Berry tackled a more serious role, playing a former drug addict struggling to regain custody of her son in Losing Isaiah (1995), starring opposite Jessica Lange. She portrayed Sandra Beecher in Race the Sun (1996), which was based on a true story, shot in Australia, and co-starred alongside Kurt Russell in Executive Decision. Beginning in 1996, she was a Revlon spokeswoman for seven years and renewed her contract in 2004.

She starred alongside Natalie Deselle Reid in the 1997 comedy film B*A*P*S. In 1998, Berry received praise for her role in Bulworth as an intelligent woman raised by activists who gives a politician (Warren Beatty) a new lease on life. The same year, she played the singer Zola Taylor, one of the three wives of pop singer Frankie Lymon, in the biopic Why Do Fools Fall in Love.

In the 1999 HBO biopic Introducing Dorothy Dandridge, she portrayed the first African American woman to be nominated for the Academy Award for Best Actress, and it was to Berry a heart-felt project that she introduced, co-produced and fought intensely for it to come through. Berry's performance was recognized with several awards, including a Primetime Emmy Award and Golden Globe Award.

Berry portrayed the mutant superhero Storm in the film adaptation of the comic book series X-Men (2000) and its sequels, X2 (2003), X-Men: The Last Stand (2006) and X-Men: Days of Future Past (2014). In 2001, Berry appeared in the film Swordfish, which featured her first topless scene. At first, she was opposed to a sunbathing scene in the film in which she would appear topless, but Berry eventually agreed. Some people attributed her change of heart to a substantial increase in the amount Warner Bros. offered her; she was reportedly paid an additional $500,000 for the short scene. Berry denied these stories, telling one interviewer that they amused her and "made for great publicity for the movie." After turning down numerous roles that required nudity, she said she decided to make Swordfish because her then-husband, Eric Benét, supported her and encouraged her to take risks.

Berry appeared as Leticia Musgrove, the troubled wife of an executed murderer (Sean Combs), in the 2001 feature film Monster's Ball. Her performance was awarded the National Board of Review and the Screen Actors Guild Award for Best Actress; in an interesting coincidence she became the first African American woman to win the Academy Award for Best Actress (earlier in her career, she portrayed Dorothy Dandridge, the first African American to be nominated for Best Actress, and who was born at the same hospital as Berry, in Cleveland, Ohio). The NAACP issued the statement: "Congratulations to Halle Berry and Denzel Washington for giving us hope and making us proud. If this is a sign that Hollywood is finally ready to give opportunity and judge performance based on skill and not on skin color then it is a good thing." This role generated controversy. Her graphic nude love scene with a racist character played by co-star Billy Bob Thornton was the subject of much media chatter and discussion among African Americans. Many in the African-American community were critical of Berry for taking the part. Berry responded: "I don't really see a reason to ever go that far again. That was a unique movie. That scene was special and pivotal and needed to be there, and it would be a really special script that would require something like that again."

Berry asked for a higher fee for Revlon advertisements after winning the Oscar. Ron Perelman, the cosmetics firm's chief, congratulated her, saying how happy he was that she modeled for his company. She replied, "Of course, you'll have to pay me more." Perelman stalked off in a rage. In accepting her award, she gave an acceptance speech honoring previous black actresses who had never had the opportunity. She said, "This moment is so much bigger than me. This is for every nameless, faceless woman of color who now has a chance tonight because this door has been opened."

As Bond girl Giacinta 'Jinx' Johnson in the 2002 blockbuster Die Another Day, Berry recreated a scene from Dr. No, emerging from the surf to be greeted by James Bond as Ursula Andress had 40 years earlier. Lindy Hemming, costume designer on Die Another Day, had insisted that Berry wear a bikini and knife as a homage. Berry has said of the scene: "It's splashy", "exciting", "sexy", "provocative" and "it will keep me still out there after winning an Oscar." According to an ITV news poll, Jinx was voted the fourth toughest girl on screen of all time. Berry was hurt during filming when debris from a smoke grenade flew into her eye. It was removed in a 30-minute operation. After Berry won the Academy Award, rewrites were commissioned to give her more screentime for X2.

She starred in the psychological thriller Gothika opposite Robert Downey, Jr. in November 2003, during which she broke her arm in a scene with Downey, who twisted her arm too hard. Production was halted for eight weeks. It was a moderate hit at the United States box office, taking in $60 million; it earned another $80 million abroad. Berry appeared in the nu metal band Limp Bizkit's music video for "Behind Blue Eyes" for the motion picture soundtrack for the film. The same year, she was named No. 1 in FHM's 100 Sexiest Women in the World poll.

Berry starred as the title role in the film Catwoman, for which she received US$12.5 million. and is widely regarded by critics as one of the worst films ever made. She was awarded the Worst Actress Razzie Award for her performance; she appeared at the ceremony to accept the award in person (while holding her Oscar from Monster's Ball) with a sense of humor, considering it an experience of the "rock bottom" in order to be "at the top." Holding the Academy Award in one hand and the Razzie in the other she said, "I never in my life thought that I would be up here, winning a Razzie! It's not like I ever aspired to be here, but thank you. When I was a kid, my mother told me that if you could not be a good loser, then there's no way you could be a good winner."

Her next film appearance was in the Oprah Winfrey-produced ABC television movie Their Eyes Were Watching God (2005), an adaptation of Zora Neale Hurston's novel, with Berry portraying a free-spirited woman whose unconventional sexual mores upset her 1920s contemporaries in a small community. She received her second Primetime Emmy Award nomination for her role. Also in 2005, she served as an executive producer in Lackawanna Blues, and landed her voice for the character of Cappy, one of the many mechanical beings in the animated feature Robots.

In the thriller Perfect Stranger (2007), Berry starred with Bruce Willis, playing a reporter who goes undercover to uncover the killer of her childhood friend. The film grossed a modest US$73 million worldwide, and received lukewarm reviews from critics, who felt that despite the presence of Berry and Willis, it is "too convoluted to work, and features a twist ending that's irritating and superfluous." Her next 2007 film release was the drama Things We Lost in the Fire, co-starring Benicio del Toro, where she took on the role of a recent widow befriending the troubled friend of her late husband. The film was the first time in which she worked with a female director, Danish Susanne Bier, giving her a new feeling of "thinking the same way," which she appreciated. While the film made US$8.6 million in its global theatrical run, it garnered positive reviews from writers; The Austin Chronicle found the film to be "an impeccably constructed and perfectly paced drama of domestic and internal volatility" and felt that "Berry is brilliant here, as good as she's ever been."

In April 2007, Berry was awarded a star on the Hollywood Walk of Fame in front of the Kodak Theatre at 6801 Hollywood Boulevard for her contributions to the film industry, and by the end of the decade, she established herself as one of the highest-paid actresses in Hollywood, earning an estimated $10 million per film.

In the independent drama Frankie and Alice (2010), Berry played the leading role of a young multiracial American woman with dissociative identity disorder struggling against her alter personality to retain her true self. The film received a limited theatrical release, to a mixed critical response. The Hollywood Reporter nevertheless described the film as "a well-wrought psychological drama that delves into the dark side of one woman's psyche" and found Berry to be "spellbinding" in it. She earned the African-American Film Critics Association Award for Best Actress and a Golden Globe Award nomination for Best Actress – Motion Picture Drama. She next made part of a large ensemble cast in Garry Marshall's romantic comedy New Year's Eve (2011), with Michelle Pfeiffer, Jessica Biel, Robert De Niro, Josh Duhamel, Zac Efron, Sarah Jessica Parker, and Sofía Vergara, among many others. In the film, she took on the supporting role of a nurse befriending a man in the final stages (De Niro). While the film was panned by critics, it made US$142 million worldwide.

In 2012, Berry starred as an expert diver tutor alongside then-husband Olivier Martinez in the little-seen thriller Dark Tide, and led an ensemble cast opposite Tom Hanks and Jim Broadbent in The Wachowskis's epic science fiction film Cloud Atlas (2012), with each of the actors playing six different characters across a period of five centuries. Budgeted at US$128.8 million, Cloud Atlas made US$130.4 million worldwide, and garnered polarized reactions from both critics and audiences.

Berry appeared in a segment of the independent anthology comedy Movie 43 (2013), which the Chicago Sun-Times called "the Citizen Kane of awful." Berry found greater success with her next performance, as a 9-1-1 operator receiving a call from a girl kidnapped by a serial killer, in the crime thriller The Call (2013). Berry was drawn to "the idea of being a part of a movie that was so empowering for women. We don't often get to play roles like this, where ordinary people become heroic and do something extraordinary." Manohla Dargis of The New York Times found the film to be "an effectively creepy thriller," while reviewer Dwight Brown felt that "the script gives Berry a blue-collar character she can make accessible, vulnerable and gutsy[...]." The Call was a sleeper hit, grossing US$68.6 million around the globe.

In 2014, Berry signed on to star and serve as a co-executive producer in CBS drama series Extant, where she took on the role of Molly Woods, an astronaut who struggles to reconnect with her husband and android son after spending 13 months in space. The show ran for two seasons until 2015, receiving largely positive reviews from critics. USA Today remarked: "She [Halle Berry] brings a dignity and gravity to Molly, a projected intelligence that allows you to buy her as an astronaut and to see what has happened to her as frightening rather than ridiculous. Berry's all in, and you float along." Also in 2014, Berry launched a new production company, 606 Films, with producing partner Elaine Goldsmith-Thomas. It is named after the Anti-Paparazzi Bill, SB 606, that the actress pushed for and which was signed into law by California Governor Jerry Brown in the fall of 2013. The new company emerged as part of a deal for Berry to work in Extant.

In the stand-up comedy concert film Kevin Hart: What Now? (2016), Berry appeared as herself, opposite Kevin Hart, attending a poker game event that goes horribly wrong. She provided uncredited vocals to the song, "Calling All My Lovelies" by Bruno Mars from his third studio album, 24K Magic (2016). Kidnap, an abduction thriller Berry filmed in 2014, was released in 2017. In the film, she starred as a diner waitress tailing a vehicle when her son is kidnapped by its occupants. Kidnap grossed US$34 million and garnered mixed reviews from writers, who felt that it "strays into poorly scripted exploitation too often to take advantage of its pulpy premise — or the still-impressive talents of [Berry]." She next played an agent employed by a secret American spy organisation in the action comedy sequel Kingsman: The Golden Circle (2017), as part of an ensemble cast, consisting of Colin Firth, Taron Egerton, Mark Strong, Julianne Moore, and Elton John. While critical response towards the film was mixed, it made US$414 million worldwide.

Alongside Daniel Craig, Berry starred as a working-class mother during the 1992 Los Angeles riots in Deniz Gamze Ergüven's drama Kings (2017). The film found a limited theatrical release following its initial screening at the Toronto International Film Festival, and as part of an overall lukewarm reception, Variety noted: "It should be said that Berry has given some of the best and worst performances of the past quarter-century, but this is perhaps the only one that swings to both extremes in the same movie." Berry competed against James Corden in the first rap battle on the first episode of TBS's Drop the Mic, originally aired on October 24, 2017.

She played Sofia, an assassin, in the film John Wick: Chapter 3 – Parabellum, which was released on May 17, 2019, by Lionsgate. She is, as of February 2019, executive producer of the BET television series Boomerang, based on the film in which she starred. The series premiered February 12, 2019.

Berry made her directorial debut with the feature Bruised in which she plays a disgraced MMA fighter named Jackie Justice, who reconnects with her estranged son. The film premiered at the Toronto International Film Festival in September 2020 and was released on Netflix in November 2021. Berry received a positive review from Deadline for her performance.

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