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1997–2015: Early life
Maymay Entrata was born in Camiguin on May 6, 1997. She and her older brother Vincent were left in the care of their grandparents in Cagayan De Oro as their father left them behind when she was just a year old, and her mother, Lorna, decided to work in Japan to provide for the whole family. Entrata also has a younger half brother named Rio from her mother's family in Japan.

Entrata was a college junior studying technology communication management at the Mindanao University of Science and Technology but she placed it on hold when she joined Pinoy Big Brother. During an interview in 2019, she mentioned that in school, she was more into social studies, arts and music, and extra-curricular activities like dancing and other events. She stated that Mathematics and English are not her best subjects; that is why when she entered the collegiate level, she chose to major in the latter to improve on the language.

Starting at the age of 14, Entrata began auditioning for various reality television shows to fulfill her ambition of becoming an actress. She first attempted auditioning for Pinoy Big Brother: Teen Clash 2010 when she was in high school but was unfortunately rebuffed. Five years later, she tried joining the same show's sixth season: Pinoy Big Brother: 737 but also failed. Entrata also tried her luck at talent competition television series like The Voice, and Pilipinas Got Talent but she also did not make it.

2016–2017: Pinoy Big Brother and career beginnings
After being rejected several times, Entrata almost did not audition for Pinoy Big Brother: Lucky 7 however, when her grandfather Joe got ill, she saw it as a reason to try again. She underwent several audition process before finally succeeding on joining the show. During the show’s duration, Entrata’s grandfather died due to cardiac arrest and she had to temporarily exit the house to visit his wake in Camiguin. While inside the PBB house, Entrata wrote and recorded the song "Baliw" ("Crazy") which was released by Star Music in different music streaming media. Entrata was later announced as a semifinalist on the show and has to temporarily exit due to the program's format. Meanwhile, Entrata, together with the other semifinalists, Edward Barber, and Kisses Delavin, took part in an online reality series called Follow the Lucky 3 Teens, which follows their journey after momentarily exiting the house. Entrata went on to win the competition on March 5, 2017, at the Alonte Sports Arena, earning 42.71% of the votes against runners-up Delavin, Yong Muhajil, and Barber.

After winning Pinoy Big Brother, Entrata began her acting career with a lead role in her lifestory episode of the ABS-CBN drama anthology series Maalaala Mo Kaya. A month after her TV debut, she signed a recording contract with Star Music. In May 2017. Entrata made her film debut in the romantic comedy film Loving in Tandem, in which she played the lead role of a happy-go-lucky girl named Shine, a young woman trying to make ends meet for her family. The film was co-starred by her fellow Pinoy Big Brother contestants Barber, Delavin, and Marco Gallo. Oggs Cruz of Rappler considered the film to be "surprisingly charming" and credited Entrata for her "dignified performance, one that is grounded not in discrepancy but on very relatable appeal". Her performance earned her a nomination for New Movie Actress of the Year at the PMPC Star Awards for Movies.

Following her lead role in Maalaala Mo Kaya, Entrata took on a supporting role at the horror-fantasy drama television series La Luna Sangre—the third installment of Lobo and a sequel to Imortal, starring Kathryn Bernardo and Daniel Padilla. In June 21, 2017, she launched her eponymous debut album at the SM North EDSA SkyDome, selling 2,000 physical copies at the venue alone, and over 7,500 copies on the day of its release. It was later certified gold on June 26, 2017, and platinum, on September 17, 2017, by the Philippine Association of the Record Industry (PARI).

2018–present: Expanding her career
To further expand her musical career, Entrata headlined her The Dream concert on February 23, 2018 at the Kia Theater (now New Frontier), where she was accompanied by Barber, Enchong Dee, and the 4th Impact. The concert's success led her to embarked on The Dream Tour to promote her music.

After her tour, Entrata appeared at the horror comedy Da One That Ghost Away, starring Kim Chiu and Ryan Bang. Oggs Cruz considered the film as a "complete and utter mess" and described her character as "blatantly useless".