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painter and scene-painter, set sail from Liverpool, England, in the Adventure with his wife Elizabeth, née Finch, and their six children: Eliza, Edward , Ann, Robert, Mary and Henry. After reaching Sydney on 2 May 1833, the family lived for a short time in Macquarie Place where the eldest son, Edward, advertised as a silhouette portraitist. By the end of the month they had moved to 3 Hunter Street. There Mrs Winstanley advertised as a bonnet-maker and Edward as a 'profile-taker’. Winstanley himself first advertised in the press as a 'Sign and Ornamental Painter’ on 10 July. Later in the month the Sydney Monitor reported that he had 'turned out some very superior paintings as sign boards’.
Although continuing to describe himself as a sign-painter until at least 1837, in June 1834 Winstanley replaced H. Allen as scene-painter at the Theatre Royal. His scenes for the London burletta Tom and Jerry , which opened on 4 June, were described in the Sydney Monitor as 'very well executed and easily recognized by those lately in London’ with the exception of 'Fleet Street, which nobody new [sic]’. He continued as scene-painter until the season closed on 31 October, being joined by Edward during the last month to form 'Winstanley & Son: Scene Painters’.
For the benefit performance of the theatre mechanist B.A. Phillips on 22 October, Winstanley advertised 'a Splendid New Scene, showing the effect of a Snow Storm, copied from the celebrated scene by Stanfield, of the Theatre Royal Drury Lane…of Napoleon crossing the Alps’. Due to a squabble between Phillips and two of the cast, however, the production had to be withdrawn at the last minute and it is not known whether Winstanley’s alpine scene was ever exhibited or, indeed, completed. The other advertised production, The Demon; or, the Magic Rose , was apparently performed as planned with Winstanley’s new scenery: Fairy Bower, by Daylight , Celestial Regions, Silver Lake, by Moonlight , A Landscape, by Twilight and Splendid Steel Castle of the Nymph of the Rose .
Winstanley took his own benefit performance on 31 October, the last night of the season. In publicising this event the Sydney Times hoped for 'a crowded and fashionable audience, whose attendance will convince Mr Winstanley of the high repute in which he is held as scene-painter to the establishment’. Winstanley’s elder daughters took part in the mixed programme arranged for the occasion, Eliza taking the title role in Clari; or, the Maid of Milan and Ann performing various songs and recitatives. Ann had been appearing regularly at the Theatre Royal since her debut in a special juvenile performance in May, but Winstanley’s benefit marked for Eliza 'her first appearance on any Stage’. Earlier in the month 'Mr Winstanley’ had appeared in the cast of Rob Roy MacGregor , although it is unclear from the newspaper reports whether it was father or son who enjoyed this brief thespian experience.
Winstanley painted the scenery for the little theatre incorporated in the temporary ballroom erected at Sir John Jamison’s home, Regentville, near Penrith, for a fancy-dress ball held there on 12 March 1835. There were two scenes: one a stock 'mountain-scenery and waterfall’, the other a novel representation of 'native lad and lass dancing in cornfields, surrounded by various Australianemblems’.
When new lessees re-opened the Theatre Royal on 4 May 1835 the proscenium was described as newly designed and painted by Mr Winstanley. The scene-painters were announced as a combination of Mr Winstanley & Son and Mr Allen & Son. Their new scene Edinburgh Castle, by Moonlight for The Heart of Midlothian , painted 'from a view lately published in the Penny Magazine’, was reported as being so popular on its first appearance on 11 May that the play was repeated three nights later. Winstanley and Allen continued as joint scene-painters at least until December 1835 when the lease of the theatre was transferred to Joseph Simmons. By 1836 Edward Shribbs was the scene-painter.
Shribbs and Winstanley were both employed by Joseph Wyatt as scene-painters for his new Royal Victoria Theatre, which opened in Pitt Street on 26 March 1838. The press advertisements credited them both with the scenery for the opening production of Othello , although the handbill of the day nominated Winstanley merely as Shribbs’s assistant. The Sydney Gazette particularly admired 'a beautifully finished representation of a Venetian wharf and piazza’ but it is impossible to identify which artist was responsible for it. The Commercial Journal , which paid particular attention in its columns to the opening season of the Royal Victoria Theatre until its representative was barred from entering the theatre on 21 April, complained about the performance of 19 April: 'The want of scenery was never more felt than on Thursday night in “Married Life”, not a scene was correct, and the inside of a cottage to represent London lodgings was “too bad”’. The theatre’s Venetian drop-scene, which the Sydney Herald called 'heavy and unmeaning’, proved so unpopular that when a new season opened at the Royal Victoria in October the Sydney Gazette announced that a new drop-scene by Fitchett & Strong would 'replace the stupid-looking affair which served that purpose during the late season’. It seems that the partnership of Shribbs and Winstanley was not considered a success and it lasted only for the Royal Victoria’s first season, i.e. from March to September 1838.
It is not clear from the records whether Winstanley left the Royal Victoria Theatre at this juncture or whether he merely assumed a less conspicuous role in the scenic department. If indeed he left the theatre it is not known how he earned his living for the next three and a half years. Presumably he would have returned to his career as a sign-painter, and Maclehose’s Directory did list him as a painter (not 'artist’ or scene-painter) of Kent Street South in 1839. According to Oppenheim, Emanuel Solomon (who built the Queen’s Theatre in Adelaide) wrote to his brother Vaiben in Sydney suggesting that 'if Mr Winstanley and his daughters would come down you might guarantee him 9 pounds per week’. The Winstanleys did not take up this offer; instead the position of scene-painter to the Queen’s Theatre, Adelaide – which opened on 11 January 1841 – was taken by Edward Opie .
Winstanley died at his residence in Elizabeth Street, Sydney, on 7 February 1842. Both Eliza and Ann were engaged at the Olympic Theatre at the time. In keeping with the tradition of 'the show must go on’ they performed on the night of their father’s death, whereupon the Sydney Gazette professed itself 'astonished how these ladies could find nerve enough to continue the performances after receiving so distressing a blow’. Winstanley was buried two days later at the Devonshire Street Cemetery; his age at his death was given as fifty-four. His widow kept a tobacconist’s shop in Pitt Street in 1844 and in King Street in 1847. She died at Fitzroy, Melbourne, in 1867. At least four children survived him: Edward, who had a short but successful career as an artist; Eliza and Ann who, as Mrs O’Flaherty and Mrs Ximenes respectively, had successful careers on the stage; and Robert, who became a dentist. At least two children, Caroline and William junior, were born in Sydney but died as infants: the former in 1835 and the latter in 1839.
Nothing is known of Winstanley’s antecedents, although he was possibly a connection of the Lancashire Winstanleys who included Hamlet, a painter-engraver, William, proprietor of Winstanley’s Water Theatre and designer of the Eddystone lighthouse, and Thomas, art auctioneer of Liverpool and London. He may also have been related to the convict James Winstanley who obtained his ticket of leave in the Bathurst district (New South Wales) on 30 June 1828 and who was himself working at the Royal Victoria Theatre, presumably as a stagehand, in September 1844 when a fire was started among some props stored in the theatre’s loft.