Jonathan Stuart Bailey was born on 25 April 1988, in Wallingford, Oxfordshire,[1] the son of an audiologist mother and a father who was the managing director of Rowse Honey.

[3][8] After securing a talent agent at 15 years old and booking acting roles, he eventually declined his university acceptance offer and opted not to go to drama school,[9][10] later saying that this kept him grounded in the performing arts: "I've never gone in as the overdog, and that's liberating and I don't want that to ever change.

"[11][12] Through his dance club in Henley-on-Thames, Bailey auditioned for and landed the alternating roles of Tiny Tim and Young Scrooge in the 1995 Royal Shakespeare Company (RSC) production of A Christmas Carol at the Barbican Theatre in London at seven years old.

[19] In 2006, on the last day of his A levels, he started rehearsing for a revival of the play Beautiful Thing in London, taking over the lead role from Andrew Garfield.

Hytner also directed Bailey in one of the vignettes for National Theatre Live: 50 Years On Stage where he played Valentine Coverly from Tom Stoppard's Arcadia.

[38] Bailey originated the role of Tim Price in Duncan Sheik's musical American Psycho directed by Rupert Goold at the Almeida Theatre.

[44] In 2016, Bailey starred as Sam, a sex-obsessed estate agent in Phoebe Waller-Bridge's first television project Crashing that W magazine described as a "twisted version of Friends".

The Stage's Mark Shenton called the production "poignant" turning "each song into a masterclass of storytelling" with Bailey "a real vocal surprise with his haunting renditions of 'If I Didn't Believe in You' and 'Nobody Needs to Know'.

"[46] Edward Seckerson of The Arts Desk wrote, in his five-star review, that Bailey was "sensationally good" and delivered tour-de-force musical performances of "Moving Too Fast" and "The Schmuel Song".

[56] Per The Times, Bailey "received an ovation every night after completing the infamous 'Getting Married Today' a rat-tat-tat, mile-a-minute technical feat, lyrically, about marriage jitters.

"[7] His "lightning-fast, show-stopping rendition of the song became a must-see West End event" according to Variety, and won him the 2019 Laurence Olivier Award for Best Actor in a Supporting Role in a Musical.

[62][63][64] The Daily Beast elaborating on Bailey's "exquisite lead performance", wrote that "he has an exceptional ability to carry his angst, pain, and guilt with him without bogging down things into a somber drag.

"[65] Bailey headlined the acclaimed[66] 2022 West End revival of Mike Bartlett's play Cock at the Ambassadors Theatre, reuniting him with his Company director Elliot.

[70] In the lead role, Bailey's "terrific performance"[71] was "utterly captivating",[72] with Variety noting that his "whiplash comic timing lifts his character from self-obsessed to scintillating, a quality he uses both artfully and artlessly.

[79] He was deemed a standout by critics with The Guardian writing that he "uncorks an outrageous scene-stealer as the hetero-camp Fiyero",[80][81] and ABC News noting that his performance was a "display of song, dance and acting virtuosity".

"[92] Describing Bailey's off-screen persona, The Cut's Kerensa Cadenas noted that talking to him is "a lesson in charm – he's personable, super-handsome, and utterly hilarious.

"[93] Pride declared that he is proof gay actors can convincingly play straight roles,[100] with Out writing that Bailey's visibility is inspiring LGBTQ+ performers to come out.

[103][104][5] In 2018, he hiked the Everest Base Camp in Nepal; the following year, he participated in the National Three Peaks Challenge to raise money for the Scottish branch of the Motor Neurone Disease Association.

[108][109] Although cautious of discussing his sexuality, which he sees as a personal matter that "becomes a commodity and a currency",[6] he is committed to visibility and representation saying: "If I can fill spaces that I didn't have growing up then I feel like that's a really brilliant thing.

[6] In 2024, Bailey launched the charity The Shameless Fund that "aims to help members of the queer community across the world live freely and authentically" by raising money through celebrity and brand partnerships.