Beginnings as a child actor (1995–2010) where Bailey made his professional acting debut at the age of seven for the
Royal Shakespeare Company 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. He sang "
Where Is Love?" from
Oliver! for his audition. The following year, he made his television debut in the
Victorian period drama
Bramwell. Bailey also played Little Baptiste in the RSC's 1996 production of
Les Enfants du Paradis. By eight years old, he was performing as
Gavroche in a
West End production of
Les Misérables. He has also done
pantomime in a production of
Peter Pan at
The Hexagon playing Michael Darling. In 2001, Bailey played
Prince Arthur for the
RSC's
King John. He made his feature film debut in 2004 in
Five Children and It, a film adaptation of
E. Nesbit's
fantasy novel of the same name. 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. That role was followed by guest roles in long-running
British television staples like
Doctors and
The Bill. His first leading role on television was in the 2009
BBC sitcom
Off the Hook about a group of first-year university students.
Television breakthrough and success on stage (2011–2019) In 2011, Bailey played the titular
Leonardo da Vinci in the 2011
CBBC action-adventure series
Leonardo, which follows a young Leonardo and his friends in 15th century
Florence. and received four
KidScreen Awards. The same year, he starred in the comedy
Campus, a semi-
improvised sitcom in which he played Flatpack, a student athlete with Olympic potential. Bailey was nominated for Outstanding Newcomer at the
Evening Standard Theatre Awards for his performance in
David Hare's play
South Downs at
Minerva Theatre in 2011, and its later transfer to
Harold Pinter Theatre the following year.
The Telegraph described him as a future star and one of "the brightest up-and-coming actors currently starring on the West End stage." He also led the
Disney Channel musical-comedy
Groove High playing the
popstar Tom that ran from 2012 to 2013 for 26 episodes and was a mixture of live action and animation where Bailey sang and also did the voiceover of his character's animated form. In 2013, Bailey rose to popularity for playing the local journalist Olly Stevens in the first two series of the hit crime-drama
Broadchurch on
ITV. On stage, he was cast by then
Royal National Theatre's artistic director
Nicholas Hytner as Cassio in his production of
William Shakespeare's
Othello at the
Olivier Theatre in 2013. Bailey considers this his "big break" with Hytner also becoming his mentor. The production was shown to cinemas via
National Theatre Live. His "likable, open-faced", and "smoothly ambitious" Cassio was "splendid", per
The Washington Post. 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. Bailey originated the role of Tim Price in
Duncan Sheik's musical
American Psycho directed by
Rupert Goold at the
Almeida Theatre. He then guest starred in the
Doctor Who episode "
Time Heist" in 2014. The episode was described by
The Independent as "a fast-paced caper" with Bailey stealing the show with his compelling performance as augmented human Psi. He also had a supporting role in the period film
Testament of Youth (2014). Bailey returned to comedy in BBC's satirical show
W1A as Jack, a role he would play for three series. 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 same year, he headlined the London production of the musical
The Last Five Years as Jamie with music, lyrics, and direction by
Jason Robert Brown at
St. James Theatre.
The Stages
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'."
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". Bailey appeared alongside
Ian McKellen in the acclaimed production of
King Lear at
Chichester Festival Theatre in 2017. He received rave reviews Bailey also made a guest appearance in series two episode two of
Michaela Coel's sitcom
Chewing Gum in 2017 where he played Ash, a romantic interest to Coel's character Tracey. With 2017's release of the video game expansion
Final Fantasy XIV: Stormblood, Bailey would begin voicing the character G'raha Tia, a role that he has continued since in further
Final Fantasy XIV expansions
Shadowbringers (2019),
Endwalker (2021) and
Dawntrail (2024). Bailey has cited enjoyment of the role and praised the writing as almost
Shakespearian. From February to April 2018, Bailey starred in
Donmar Warehouse-
Sheffield Theatres co-production of
Peter Gill's
The York Realist. The
Evening Standard,
The Arts Desk, and
Sunday Express gave the production five stars, with
The Independent calling it "a pitch-perfect, impeccably acted production" in its own five-star review. Bailey joined the
2018 West End production of
Stephen Sondheim's
Company directed by
Marianne Elliott. He originated the gender-swapped role of Jamie which was initially written as a female character named Amy. 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."
International recognition and work on film (2020–present) Since 2020, Bailey has starred in the
Shondaland-produced
Netflix series
Bridgerton, an adaptation of
Julia Quinn's
Regency romance novels, as
Anthony, 9th Viscount Bridgerton. His portrayal was critically acclaimed, and gained him wide recognition. The
second series, which centered around his character, became the
most watched English-language television series on Netflix at the time.
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." Bailey headlined the acclaimed 2022 West End revival of
Mike Bartlett's play
Cock at the
Ambassadors Theatre, reuniting him with his
Company director Elliot.
The Observer called it an "immaculate production", with
The Arts Desk writing that it was "brutal, bruising, and brilliant". In the lead role, Bailey's "terrific performance" was "utterly captivating", with
Variety noting that his "whiplash comic timing lifts his character from self-obsessed to scintillating, a quality he uses both artfully and artlessly." In 2023, Bailey starred opposite
Matt Bomer in the
Showtime adaptation of
Fellow Travelers. His performance was described by
The Washington Post as "sensational" and won him a
Critics' Choice Award for Best Supporting Actor in a Miniseries and earned him a nomination for a
Primetime Emmy Award for Outstanding Supporting Actor in a Limited or Anthology Series or Movie. The following year, he had a guest appearance in the third series of the teen drama
Heartstopper. Bailey played
Fiyero in the musical fantasy films
Wicked (2024), based on the
musical of the same name. He was deemed a standout by critics with
The Guardian writing that he "uncorks an outrageous scene-stealer as the
hetero-
camp Fiyero", and
ABC News noting that his performance was a "display of song, dance and acting virtuosity". He contributed to the
film's soundtrack with the song "
Dancing Through Life", which debuted at number 90 on
Billboard Hot 100, peaking at number eighty-six. His performance earned him a nomination for a
Actor Award for Outstanding Performance by a Male Actor in a Supporting Role, alongside another nomination for the film's cast for
Outstanding Performance by a Cast in a Motion Picture. Bailey played the titular role of
Richard II at the
Bridge Theatre in
Nicholas Hytner's production of
Shakespeare's
play of the
same name until May 2025. His performance received positive reviews from critics and he was nominated for
Best Actor at the
Evening Standard Theatre Awards. The same year, Bailey starred in the science fiction film
Jurassic World Rebirth directed by
Gareth Edwards and reprised his role as Fiyero in the musical fantasy film
Wicked: For Good. The box office successes of the two films made him the highest grossing actor of 2025. In the summer of 2027, Bailey will star opposite his
Wicked co-star
Ariana Grande in
Marianne Elliott's
Barbican Theatre production of
Sunday in the Park with George. == Public image ==