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She wanted a career with impact and envisioned a career in writing or journalism, but Hall's first semester of graduate school changed drastically when her father died of a stroke. "It was sudden. And I think when sudden events that are painful happen in your life, you know, they redirect your course," Hall reflected. "When you’re young, you don’t grasp the gravity of life. But when you lose someone that you spend most of your life with, and you’re young, you do. And so I think that started me thinking about what I really wanted to do in life. And I know my father would have wanted me to finish school. So I did that." She began a career in the entertainment industry, starting off with a guest appearance on Sadat X's 1996 album Wild Cowboys on the track, "The Interview".

She received critical acclaim for starring as Lisa Conroy in the comedy film Support the Girls (2018), becoming the first African American to win the New York Film Critics Circle Award for Best Actress, and received nominations for the Gotham Award and Independent Spirit Award for Best Actress.

In 2018, Hall was part of the ensemble cast in The Hate U Give. She also had the lead in Support the Girls, a film directed by Andrew Bujalski. For the latter, she received critical praise, and was nominated for several awards, winning the New York Film Critics Circle Award for Best Actress. She is the first African-American to win the award. In 2019, Hall hosted the 2019 BET Awards.

In 2017, Hall co-starred in the comedy film Girls Trip, which became a critical and commercial success.

In 2016, Hall was in Barbershop: The Next Cut. She played the role of Angie, one of the hair stylists, alongside Ice Cube, Common, and Eve.

In the 2015 film People Place Things, Hall had a major role as the love interest of a newly divorced man.

Hall appeared in the 2014 film About Last Night, costarring Kevin Hart. She and Hart were seen as the film's highlight as they had a "great dynamic together" and the two were credited with having the funniest lines in the film. All of the cast was seen as having a "perfect mix of charisma and likability". Jessica Herndon of the Associated Press stated "Hart and Hall are the best part of this film. They play the couple you know all too well: fiery, able to press one another's buttons and always caught in the makeup to breakup game." Negative reviews of the film also praised the pairing of Hall with Kevin Hart. Mick LaSalle of The San Francisco Chronicle expressed that Hart was "well paired for Hall, who matches him for comedy." At the time of the film's release, both Hall and Hart expressed interest in working on other projects together. About Last Night was her third ensemble film and Hall reflected that she learned from actors she worked with in ensembles.

Hall reprised her role as Candace Hall in Think Like a Man Too. She revealed what members of the cast partied the most in the film shortly before the movie's release. "Everyone kind of had their fun, I'm not gonna lie. We went out, we gambled. Kevin [Hart] parties. There were parties, and we all went. It was good fun". In July 2014, it was announced Hall would star in a Lifetime film, entitled With This Ring, with Eve and Jill Scott.

In 2014, she signed as an ambassador for Elizabeth Taylor's White Diamonds. Hall has also voiced her admiration for Taylor. "I love Elizabeth Taylor. The reason I always was such a fan, I read her The New York Times bestseller. She was one of the people who I felt equally possessed the same amount of talent as she did beauty. Her work that she did throughout her entire career–I watched her on General Hospital and what I always loved about her was that she was elegant. Whenever I do red carpet looks one of the things that I like is to always make sure that there’s a sense of elegance and class. And I felt like she always exuded that."

In 2012, she portrayed Candace Hall in Steve Harvey's movie Think Like a Man, a romantic comedy based on his book Act Like a Lady, Think Like a Man. Hall reprised her role as Candace Sparks in The Best Man Holiday in 2013. She believed the characters had evolved from the first film. Hall felt The Best Man Holiday was different from any sequel she had ever done before since it was not "immediate" and it had been fourteen years since the release of the original. Hall felt the first film had "the joy of the wedding" and in the sequel "they come together for the holidays, but it's deeper than that. This one's definitely different, but we still laughed. There was so much laughter behind the scenes." Hall joked about how all of the male members of the cast were married while all of the women were not, stating that Morris Chestnut was happily married while walking around "with his shirt off!"

In 2010, when she was 40, Hall unsuccessfully tried to become a nun after a bad break-up, having previously wanted to become a nun at the age of 14. She was refused for being too old, as the cut-off age is 39.

She appeared in the film Law Abiding Citizen in 2009. She had a role in the 2010 Danneel Harris and Arielle Kebbel film Mardi Gras. From its fall 2010 debut until a series overhaul in January 2011, Regina Hall portrayed Deputy District Attorney Evelyn Price on Law & Order: LA. In addition to being an actress and advocate, Regina Hall announced in November 2010 that she is now writing for ABILITY Magazine.

Around 2004, Hall's mother was diagnosed with scleroderma, a rare autoimmune disease. When not working in Hollywood, Hall can be found volunteering for the care of senior citizens at a Sherman Oaks, California, convalescent home twice a week as well as raising public awareness for the disease. "When my mom was diagnosed, I didn’t know much about the condition. But Dana Delany, who is an actress and now a friend of mine, put me in touch with Bob Saget. Bob had made a television movie about scleroderma years ago because his sister had died from it. That was back when they didn’t even know what it was. Anyway, Bob had a group called the Scleroderma Research Foundation, so I donated to that and my mother even went to the doctor Bob had suggested, who happened to be over at Johns Hopkins."

Hall gained more recognition with her role in the comedy-horror-spoof Scary Movie (and the sequels Scary Movie 2, Scary Movie 3, and Scary Movie 4) portraying the sex-crazed Brenda Meeks, and the TV movie Disappearing Acts. The Scary Movie films would become some of her best known roles. In 2001, Hall landed the role of Coretta Lipp on the prime-time drama Ally McBeal, which was originally a recurring role over several episodes but was made a main character in the 5th season of the show. A year later, she starred in the action-drama Paid in Full, a film directed by Charles Stone III. Since then, she has appeared in leading roles in films such as Malibu's Most Wanted, King's Ransom and The Honeymooners.

In 1997, Hall appeared in her first television commercial at the age of 26. Her television career began with a role on the soap opera Loving, and guest appearances on the Fox police drama New York Undercover. She played Kandy in the 1999 film The Best Man. She left a lasting impression on viewers with her portrayal of the character Candace "Candy" Sparks. Hall reflected: "It was my very first movie. I met Sanaa Lathan on it, and we did Love and Basketball together, which was my second film. And then, at that point, I was visiting L.A. to stay and it led to a third film and a fourth film. And it was really a big deal because I'd never been on a set before." It signaled a pivotal point for Hall's career. As a key member of the all-star cast, she welcomed rising-star status in "black-Hollywood".

Regina Lee Hall (born 1971) is an American actress, and comedian. She has appeared in numerous television series, most prominently in a regular role on the comedy series Ally McBeal (2001–2002) and Black Monday (2019–present). Hall became known for starring as Brenda in the Scary Movie film series (2000–2005), and her other significant film roles include The Best Man (1999) and its sequel The Best Man Holiday (2013), Malibu's Most Wanted (2003), Think Like a Man (2012) and its sequel Think Like a Man Too (2014), About Last Night (2014), Vacation (2015), Girls Trip (2017), and The Hate U Give (2018).

Hall was born on December 12, 1970, in Washington, D.C., the daughter of a contractor and electrician father, Odie Hall, and a teacher mother, Ruby. After graduating from Immaculata College High School, Hall enrolled at Fordham University in the Bronx, where she graduated with a bachelor's degree in English in 1992. She later enrolled at New York University, where she earned a master's degree in journalism in 1997. Reflecting on college, Hall said: "I loved being a student. I could've gone to school until I was 75 years old as long as somebody would've paid my rent. I would've been a professional student."