Childhood & Early Life
Bailey was born Bailey Thomas Cabello May on August 6, 2002, in Cebu City, Cebu, Philippines, to British father, Matthew May, and Filipino Cebuana mother, Vanessa Cabello-May. Both his parents were singers on a cruise ship. He has a sister, Maya Luiza, and brother, Jordan. May holds the dual citizenship of Philippines and Britain.
May relocated with his family to Norwich, England, at the age of 4 and visited Philippines for holidays. In Norwich, he studied at the Notre Dame High School. He returned to the Philippines at 12 years of age after successfully auditioning online and becoming a housemate of ‘Pinoy Big Brother: 737.’ While growing up, he played soccer at a competitive level.
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He stepped into the world of entertainment by making cover songs of notable singers and posting them on the internet. He made cover versions of tracks like ‘Night Changes’ and ‘Steal My Girl’ by the British-Irish boy band ‘One Direction,’ and ‘Beautiful Girls’ by Jamaican-American reggae fusion singer, Sean Kingston. The cover of ‘Beautiful Girls’ became viral instantly giving him initial recognition.
He entered ‘Pinoy Big Brother: 737’ as one of the housemates in 2015. It was the second special and the twelfth overall season of the Philippine version of the ‘Big Brother’ reality game show franchise called ‘Pinoy Big Brother.’ May is the youngest contestant to participate in the entire ‘Big Brother’ franchise. He finished as third runner-up (4th Teen Big Placer) in the season that aired on ABS-CBN from June 20, 2015 to November 8, 2015.
The exposure and recognition through ‘Pinoy Big Brother’ helped him start his journey in the Philippine showbiz and got him his first acting assignment in the hit Philippine romantic comedy television series, ‘On the Wings of Love.’ His Pinoy Big Brother housemate, Ylona Garcia, was also introduced in the series that aired on ABS-CBN from August 10, 2015 to February 26, 2016.
Meanwhile, he joined hands with Garcia to record a version of Magmahal Muli in July 2015. The song was composed and first sung by ‘Pinoy Big Brother’ season one (2005) contestants, Sam Milby and Say Alonzo. In August 2015, May recorded a version of the track ‘Now We're Together, originally sung by Khalil Ramos. May released both the songs on Spotify on August 9, 2015.
He announced on November 11, 2015, that he would come up with his new album. He worked with Filipino pop singer Jamie Rivera who became the overall producer of his self-titled album. The album was released on November 20, 2015, on Spotify. The album included songs like ‘Build Me Up, Buttercup,’ ‘Gotta Win,’ ‘Now We're Together,’ ‘Can You Be My Girl,’ and ‘Gusto Kita,’ of which the later two were written by Rivera. He won the ‘Most Promising Male Singer/Performer of the Year’ award at the 48th GMMSF Box-Office Entertainment Awards in 2017 for ‘Bailey’.
In 2015, he performed in the ABS-CBN aired longest-running Filipino musical variety show ‘ASAP’ (All-Star Sunday Afternoon Party) and in the Philippine noontime variety show, ‘It's Showtime.’
He recorded the duet song, ‘O Pag-ibig,’ along with Garcia in March 2016. It was composed by Honlani Rabe and Jack Rufo. May and Garcia interpreted the song for the 2016 Himig Handog song competition.
‘O Pag-ibig’ won the maximum number of special awards. These include the MOR Choice Award, the TFC Global Choice Award, the One Music Philippines Favorite Interpreter Choice Award, and the MYX Best Music Video Choice Award.
He featured as a contestant in the Filipino reality music competition show, ‘We Love OPM: The Celebrity Sing-Offs,’ in the celebrity team ‘Voice Next Door’ by Richard Poon. The team also included Kyle Echarri and Juan Karlos Labajo. The show aired on ABS-CBN from May 14, 2016 to July 17, 2016.
The drama anthology series, ‘Maalaala Mo Kaya,’ saw him appearing as Daniel Padilla in the second episode of the Season 25 of the series titled ‘Autograph’ that aired on January 14, 2017.
He became a member of the global pop music group, ‘Now United,’ in 2017. The group, created by Simon Fuller and managed by XIX Entertainment, includes fourteen singing and dancing artists of different nationalities. The discography of the group that officially debuted in 2018 includes singles like ‘All Day,’ ‘What Are We Waiting For,’ and ‘Who Would Think That Love’.
He has won several awards, including the Male Breakthrough Artist of the Year at the 2015 RAWR Awards, the Male Celebrity of the Night award at the 29th PMPC Star Awards for Television and the Push Like Newcomer award at the 2016 Push Awards.
Bailey May is quite close to Garcia and there are rumours of a romantic relationship.
May’s adopted cousin, Thomas Ramirez, is also a singer who spawned hits like ‘Perdoname’ and ‘You belong to me.’
May has garnered considerable popularity on social media. His YouTube channel has amassed more than 15K subscribers. On Twitter, he has over 1.7K followers, while his Instagram account has 1.4 million followers.