In 2023, he portrayed the lead role of Manoj Kumar Sharma in the biographical film 12th Fail (2023), which emerged as a sleeper hit and earned him the Filmfare Critics Award for Best Actor.

[16] Belonging to a middle-class Christian family, originally from Shimla, Himachal Pradesh, Massey was born and raised by his parents in Mumbai, Maharashtra.

[17] Massey's educational background consists of attending St. Anthony's High School in Versova with further studies being completed from R. D. National College of Arts & Science in Bandra, Mumbai.

[22] In his first lead role, Massey portrayed Murli Laal, who is married to a dwarf Bharti in Baba Aiso Varr Dhoondo, from 2010 to 2011.

[25] Massey made his Hindi film debut in Vikramaditya Motwane's Lootera (2013), alongside Ranveer Singh and Sonakshi Sinha.

[35] In 2019, Massey appeared as a murder accused in Criminal Justice directed by Tigmanshu Dhulia and Vishal Furia,[36] Sanjukta Sharma of Scroll.in opined, "He slips into Aditya's skin without any effort showing, and makes his transformative journey compelling.

"[39] In his first film of 2020, Massey played the male lead opposite Deepika Padukone in Meghna Gulzar's Chhapaak, based on the life of acid attack survivor Laxmi Agarwal.

[40] The film was a commercial failure, but Sukanya Verma stated: "Vikrant embodies a dour faced, wry-natured activist in Fabindia kurtas quite effectively.

"[41] Massey then reunited with Shweta Tripathi in a science fiction Cargo, which also premiered at the 2019 MAMI Film Festival under the spotlight section[42][43][44] Later, he played the lead in two Netflix films: Dolly Kitty Aur Woh Chamakte Sitare opposite Bhumi Pednekar and Ginny Weds Sunny opposite Yami Gautam.

[47] After appearing in Switchh, Massey portrayed Rishabh, an electrical engineer opposite Taapsee Pannu in Haseen Dillruba, which emerged as the most-watched Hindi film on Netflix.

[54] Bollywood Hungama stated that Massey gives a "confident" performance and "suits the part", but added that in some places, he "tries" to be too funny and "fails".

[55] In 2023, Massey first played Kapil, manager of the king alongside Sara Ali Khan and Chitrangada Singh in Gaslight, which received mixed to negative reviews.

[60] Monika Rawal Kukreja of Hindustan Times termed the film his "career-best" and noted, "Massey takes the cake for delivering a brilliant performance.

[75] Some reports mention that Massey and actress Sheetal Thakur began dating in 2015, but became closer while working on the series Broken But Beautiful (2018).

[8] Asianet News termed him "one of the finest actors" of his generation and added, "Throughout his prolific career, he has consistently chosen unconventional roles that have left a lasting impression on audiences.

"[85] Film Companion noted, "Vikrant has been consistently prolific and made a mark with every performance, regardless of the scope, nature or length of a role.

"[86] Priyanka Roy from The Telegraph said, "Vikrant, who's had success across mediums, is that rare breed who doesn't shun the relatively smaller parts even when he's now transitioned to lead roles.

"[89] Hitanshi Kamdar of Grazia added, "Massey has essayed a litany of easy-going and complex characters over the course of his unmistakably impressive career trajectory.

[91] His A Death in the Gunj director Konkona Sen Sharma called him a "receptive actor" and said, "Vikrant got a sense of the character from the script and made it his own.

[96] In addition to his acting career, Massey is a celebrity endorser for brands and products such as Lenskart, Cornetto, Cadbury, ICICI Bank, Nescafé, Longines and Samsung Galaxy.