Sheader's first season, produced in 2008, consisted of productions of Romeo and Juliet, Twelfth Night, Lerner and Loewe's Gigi - starring Millicent Martin as Mamita and Topol as Honore - and an especially adapted production of A Midsummer Night's Dream for family audiences.
In 2010, the theatre presented new productions of The Crucible, The Comedy of Errors and Macbeth, which was adapted for younger audiences. The season musical was Into the Woods by Stephen Sondheim. The production starred Hannah Waddingham as the Witch, Jenna Russell as the Baker's Wife, and Helen Dallimore as Cinderella. It was the first time that Into the Woods had been performed outside and won the Olivier Award for "Best Musical Revival."
2011
The 2011 season included productions of Lord of the Flies, The Beggar's Opera, Shakespeare's Pericles and the musical Crazy for You, which received the highest number of five star reviews of any musical opening in 2011 and became the first Open Air Theatre production to transfer directly into the West End, where it played at the Novello Theatre.
2012
For the 2012 season, two productions were run across the entire season in repertoire: the Tony Award-winning Ragtime the Musical and Shakespeare’s ''A Midsummer Night’s Dream'.'
2013
The 2013 season included productions of To Kill a Mockingbird, Pride and Prejudice, The Winter's Tale and The Sound of Music.
2014
The 2014 season included productions of All My Sons, Hobson's Choice, Twelfth Night and Porgy and Bess. To Kill A Mockingbird returned to the Open Air Theatre ahead of a major UK tour.
2015
The 2015 season began with Peter Pan, directed by Sheader and Liam Steel. The Seagull and Seven Brides for Seven Brothers followed, directed respectively by Matthew Dunster and Rachel Kavanaugh. Lord of the Flies returned to the Open Air Theatre for one week, before embarking upon a major UK tour.
2016
In November 2015 the 2016 season was announced. Running Wild by Michael Morpurgo opened the season as a co-production with Chichester Festival Theatre. The play was directed by Sheader and Dale Rooks. It received a good critical response; deemed "a winner" by the Daily Telegraph. Henry V brought William Shakespeare back to the Park, and was followed by Tim Rice and Andrew Lloyd Webber's Jesus Christ Superstar, which played to sold-out audiences, also directed by Sheader. Jesus Christ Superstar won a Laurence Olivier Award for Best Musical Revival in 2017. The sell-out production of Pride and Prejudice returned at the end of the season ahead of a major UK tour.
2017
In November 2016 it was announced that On The Town would open the 2017 season, followed by Dickens Uncovered, a new adaptation of A Tale of Two Cities by Charles Dickens which would be directed by Sheader, and Oliver Twist adapted for younger audiences, Oliver Twist created for everyone aged six and over. Jesus Christ Superstar returned to conclude the season. In January 2017 it was announced that the theatre had won London Theatre of the Year at The Stage Awards.
2018
The 2018 season welcomed the return of Peter Pan, a revival of their 2015 Olivier Award-nominated production. For a limited run, in a co-production with the English National Opera, Artistic Director Timothy Sheader rediscovered Benjamin Britten's The Turn of the Screw, receiving acclaimed reviews. Max Webster directed William Shakespeare'sAs You Like It. For families, Dinosaur World Live, a new interactive show played daytime performances. The season concluded with the mean green monster musical Little Shop of Horrors, which played to critical acclaim.
2019
The 2019 season opened with Thornton Wilder’s Pulitzer Prize-winning play Our Town, directed by Ellen McDougall, Artistic Director of the Gate Theatre. Continuing their collaboration with English National Opera, they present Engelbert Humperdinck’s opera Hansel and Gretel - members of the ENO Orchestra and was conducted by Ben Glassberg, with direction by Open Air Theatre’s Artistic Director, Timothy Sheader. Dominic Hill, Artistic Director of the Citizens Theatre, Glasgow, then directed a new production of A Midsummer Night’s Dream. To conclude the season, Jamie Lloyd directed Tim Rice and Andrew Lloyd Webber’s Evita. The theatre's multi award-winning production of Jesus Christ Superstar also transferred to the Barbican Centre for just 60 performances from 4 July - 24 August 2019, prior to a 50th anniversary tour of the US.
2020
The theatre will be closed for the entirety of the 2020 season due to the COVID-19 pandemic.
2021
The 2021 season will open with a new musical 101 Dalmatians, with a book by Zinnie Harris and music and lyrics written by Douglas Hodge, based on the book by Dodie Smith. This will be followed by William Shakespeare's Romeo and Juliet directed by Kimberley Sykes and concludes with Rodgers and Hammerstein's Carousel directed by Timothy Sheader. During August 2021, the theatre will also host Dragons and Mythical Beasts. These productions were postponed from 2020 due to the COVID-19 pandemic.
Other theatre work
In 2013 Sheader directed a new production of Barnum at Chichester Festival Theatre. The previous year he directed The Magistrate at the Royal National Theatre which starred John Lithgow. At the beginning of 2015 he directed My Fair Lady at the Aarhus Teater in Denmark. Other productions that Sheader has directed include Imagine This ; Hobson's Choice, The Clandestine Marriage, Love in a Maze ; Rodgers and Hammerstein's Cinderella, The Three Musketeers ; The Star Throwers, Unless ; Misconceptions ; Streetcar to Tennessee ; Achilles ; Wild, Wild Women ; Arms and the Man Piaf, Sweet Charity. 2018 also saw Sheader's Jesus Christ Superstar play at Chicago's Lyric Opera. In 2019, Sheader directed The Monstrous Child at the Royal Opera House.
