It was purely by chance that Sinden entered the world of performing arts. There were others in his family who had tried their luck in amateur theater. Once, his cousin, Frank, had an unusual request for Sinden. He requested Sinden to replace him in an amateur production at the ‘Brighton Little Theatre.’ Frank was summoned by the ‘Royal Air Force’ (RAF) for World War II, and Sinden, who had been turned down by the naval services because of asthma, was essentially the only person of choice for Frank’s replacement.
Charles F. Smith, the director of ‘Theatre Royal’ noticed Sinden at the performance and asked him to join the company ‘Mobile Entertainments Southern Area’ (MESA), which was a local chapter of the wartime entertainment service ‘Ensa.’ In 1941, Sinden joined Smith’s group. He made his first appearance as ‘Dudley’ in ‘George and Margaret,’ in 1942. He spent the next 4 years performing modern comedies and entertaining the forces along the South Coast of England.
By then, Sinden had forgotten all about architecture. He enrolled himself at ‘Webber Douglas School of Dramatic Art’ for two terms in 1945. He joined a Leicester repertory for 6 months, before joining the ‘Shakespeare Memorial Theatre’ at Stratford-upon-Avon in 1946, where he played ‘Dumaine’ in ‘Love's Labour's Lost,’ ‘Lorenzo’ in ‘The Merchant of Venice,’ and ‘Paris’ in Peter Brook's ‘Romeo and Juliet.’
After making his ‘West End’ debut in October 1947, with ‘Richard II,’ Sinden joined the ‘Old Vic,’ performing for both its London and Bristol branches, in 1948. After a year in Bristol, Sinden returned to ‘West End’ with John Gielgud’s ‘The Heiress,’ appearing along with Ralph Richardson and Peggy Ashcroft, at ‘Theatre Royal,’ Haymarket.
In 1952, director Charles Frend spotted him in a production of ‘Red Letter Day’ and decided to cast this theater actor in 1953’s most successful film, the British war movie ‘The Cruel Sea’ by ‘Ealing Studio.’ Sinden could not have asked for a better introduction to the world of cinema, billing alongside popular British star Jack Hawkins in his first feature film.
Before ‘The Cruel See,’ he had just played a minor role in the drama film ‘Portrait from Life,’ in 1948.
Following the success of ‘The Cruel Sea,’ Sinden was signed by UK’s largest and most integrated entertainment conglomerate, ‘Rank Organisation,’ for 7 years. He starred in 23 films under the contract, which included ‘Mogambo’ (1953), ‘Doctor in the House’ (1954), ‘Above Us the Waves’ (1955), ‘The Black Tent’ (1956), ‘Eyewitness’ (1956), ‘Doctor at Large’ (1957), ‘The Siege of Sidney Street’ (1960), and ‘Twice Round the Daffodils’ (1962).
Like most actors, Sinden, too, had his “Frankenstein” of a character, a “monster” created by him that he could not dodge later: the flamboyant medical student ‘Tony Benskin’ from ‘Doctor in the House’ (1954). Sinden got typecast in comic roles or other similar characters for the next 8 years.
Sinden returned to theater productions during the early 1960s, after his cinema career came to a gradual halt. Though rejected by Peter Hall initially, Sinden claimed new heights at the newly formed ‘Royal Shakespeare Company,’ delivering some of his most revered performances both at Stratford and ‘West End’ theaters.
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One of his most notable roles was that of the ‘Duke of York,’ opposite Peggy Ashcroft’s ‘Queen Margaret,’ in John Barton’s 1963 production of ‘The Wars of the Roses,’ an epic amalgamation of Shakepeare’s historical plays, which ran at Stratford and the ‘Aldwych’ for 2 years.
‘Mr Price’ in Henry Living’s ‘Eh?’ (1964), ‘Lord Foppington’ in John Vanbrugh's ‘The Relapse’ (1967), and ‘Malvolio’ in ‘Twelfth Night’ (1969) were all highly appreciated portrayals by Sinden in that decade. His larger-than-life burlesque of ‘Malvolio,’ opposite Judi Dench’s ‘Viola,’ had never been seen before. He had two really successful runs at ‘West End,’ in Terence Frisby’s ‘There’s a Girl in My Soup’ (1966) and Ray Cooney’s ‘Not Now, Darling’ (1967).
In 1974, Sinden performed as ‘Sir Harcourt Courtly,’ alongside Dench and her husband ‘Michael Williams,’ in Ronald Eyre’s production of Dion Boucicault's ‘London Assurance’ at the ‘Albery Theatre.’ A year later, when the production moved to New York, Sinden became the first-ever recipient of the newly established ‘Broadway Drama Desk Special Award.’
Sinden’s TV career took off around the same time, in the 1970s, with a starring role as ‘David Pulman’ in ‘The Organization’. According to him, the satisfaction he drew from the stage was not enough to fill the pockets. From 1975 to 1979, Sinden played an English butler, ‘Robert,’ opposite Elaine Stritch’s sharp-tongued American author ‘Dorothy,’ in ‘Two’s Company’ for ‘London Weekend Television.’ The show received multiple ‘BAFTA’ nominations throughout its tenure, including one 'Best Light Entertainment Performance’ nomination each for Stritch and Sinden, in 1979.
While gaining wider popularity with his TV work, Sinden continued to mesmerize his theater audiences with performances in both commercial and subsidized forms. He played ‘Benedick’ in Barton’s highly acclaimed production of ‘Much Ado about Nothing,’ alongside Dench. Sinden won the ‘Evening Standard Award’ for the ‘Best Actor’ for his performance in ‘King Lear’ in 1977.
In 1979, Sinden presented a documentary series named ‘Discovering English Churches’ on ‘BBC2,’ exploring the architecture and the unique history of British churches. From 1981 until 1991, Sinden played the snooty antique dealer ‘Simon Peel’ in ‘Never the Twain’ on ‘Thames Television.’
His love for theater made him work in the 2013 documentary series ‘Great West End Theatres,’ a great narration of the history associated with each of the 40 London theatres, accompanied by amusing anecdotes. The series was directed and produced by Sinden’s younger son.
He had lent his voice to ‘Sir Charles Baskerville’ in a ‘Radio 4’ adaptation of ‘The Hound of the Baskervilles.’
Sinden wrote two autobiographies in his lifetime: ‘A Touch of the Memoirs’ (1982) and ‘Laughter in the Second Act’ (1985). His other literary works include ‘The English Country Church’ (1988) and ‘The Last Word’ (1994).