Jumayyil's collaboration with Dark Rain Entertainment continued with a series of romantic comedies, including Mee Loaybakee (2017) and Vakin Loabin (2018).

[1] Following the successful completion of his GCE Ordinary Level exams, Jumayyil's interest in pursuing a career in the film industry was nurtured by his father, Nimal.

[1] In 2014, Jumayyil made his film debut in Ahmed Nimal's Aniyaa, where he appeared alongside Niuma Mohamed, Ismail Rasheed and Fathimath Fareela.

[2][3] The film failed to generate much hype during its screening and received mixed-to-positive reviews from critics, achieving moderate success at the box office.

[4][5] The subsequent year, Jumayyil appeared in Ali Shifau-directed romantic film Emme Fahu Vindha Jehendhen opposite Mariyam Majudha, where he portrayed the role of Ryan.

[9] His performance garnered positive reviews, with Ahmed Nadheem from Avas noting significant improvement in Jumayyil's acting compared to his previous work.

[12] Later in the same year, Jumayyil appeared in Fathimath Nahula's horror film 4426, where he portrayed the character Suja, a member of a group of friends trapped in a haunted house.

[17] Featuring Ismail Zahir, Nuzuhath Shuaib, Fathimath Azifa, Ahmed Asim, Ali Azim and Neena Saleem in prominent roles, the film received mixed reviews from critics.

[26] In a pre-premiere review by Raajje.mv, Ismail Naail Nasheed praised the character development and reduced melodrama in the film, highlighting Jumayyil's versatility in portraying a range of emotions.

[26] Jumayyil's first release in 2019 was the Ahmed Sinan-directed crime thriller Goh Raalhu (2019) which delves into themes of criminality and misdemeanors as a young man strives to prove the sincerity of his love.

[27][28] It received widespread positive reviews from critics, with Aminath Luba of Sun describing it as a "five-star worthy blockbuster film" and wrote: "Jumayyil yet again proved that he is here to stay and entertain the audience with his authentic performance, no matter what the genre is".

[32][33] Later in the year, the first Maldivian anthology film was released, featuring Jumayyil as a drug dealer in the segment directed by Ravee Farooq, titled Gaathil.

[39] The last theatrical release of the year, Dark Rain Entertainment's November featured Jumayyil as a photographer who reinvents himself while searching for his lost love from a fling.

[40] Although initially scheduled for release in 2019, the film faced multiple delays during the post-production stage, partly due to the COVID-19 pandemic and also considering rape accusations against Jumayyil.