She is also notorious as a vexatious litigant, filing numerous frivolous lawsuits that led to her bankruptcy.
Born as Edna May Squires in her parents' carnival caravan in Pontyberem (about 12 miles from Llanelli), Carmarthenshire, Wales, to a steelworker, Archibald James Squires and his wife, Emily, she wanted a piano as a child. Her mother bought her a ukulele. While working in a tin plate factory, she began to perform professionally as a singer at the age of 16 in the working men's club of Pontyberem.
Squires decided to pursue her dream in London, so while working as a nurse she would audition unsuccessfully for various jobs, during which she met agent Joe Kay, who got her night time work in various clubs. While working in the East End, Squires worked at a club which gave her the name Dorothy, which she liked and used on stage after that time. Squires did most of her work with the orchestra of Billy Reid, who was her partner for many years. After she joined his orchestra in 1936, he began to write songs for her to perform.
In the immediate post-war, she worked on the BBC radio show Variety Bandbox, which subsequently made her the highest paid female singer in the UK. Squires and Reid bought a 16-bedroom house in Bexhill on Sea, and working with Reid recorded the original version of Reid's composition, "A Tree in the Meadow", best known in the United States for the recording by Margaret Whiting, which reached No.1 on the US pop chart.
Her version of another Reid-penned song, "I'm Walking Behind You" was covered by Eddie Fisher which became a No.1 hit single in the US, and her recording of "The Gypsy" also became a No.1 hit there after being waxed by The Ink Spots – their biggest hit. It was also a major hit for Dinah Shore.
Whilst working with Billy Reid, Dorothy Squires lived at 16 Chaucer Road, Herne Hill Brixton.
Squires met Roger Moore (12 years her junior) at one of her lavish parties at her mansion in Wansunt Road, Old Bexley, Kent (which has now been replaced by houses). He later became her second husband when they married in New Jersey on 6 July 1953. She said many times over the years "it started with a squabble, then he carried me off to bed." She took him to Hollywood and introduced him to various people in the film industry, and they partied with Gary Cooper, Grace Kelly, Doris Day and Rock Hudson. As his career took off, hers started to slide. Their marriage lasted until 1961, when Moore left her and moved in with Luisa Mattioli. Moore was unable to marry legally until Squires agreed to a divorce in 1969 – the day on which Squires was convicted of drunk driving.
Returning to living in the UK, Squires had a career revival in the late 1960s at the age of 55 with a set of three singles making the UK Singles Chart, including a cover of "My Way". New albums and concerts followed included a sell out set of concerts at the London Palladium. Squires herself had hired the Palladium for a series of shows, and they exceeded expectations and sold out of tickets within hours. A double album of the event was issued.
In 1971 she undertook the first of 30 court cases over the next 15 years. In 1971 she successfully sued the News of the World over the story "When Love Turned Sour", and was awarded £4,000. In 1972 she took out a libel action against the actor Kenneth More for mistakenly referring to Mattioli as Roger Moore's "wife" when he was still legally married to Squires. Michael Havers acted for Kenneth More, who won the case. In 1973 she was charged with high kicking a taxi driver who tried to throw her out of his cab. She was also one of several artists charged with allegedly trying to bribe a BBC radio producer as part of a scheme to make him play her records; the case was dropped.
In 1974 her Bexley mansion burned down, from which she escaped with her dog and all her love letters from Roger Moore. She then moved into a house in Bray next to the River Thames, which flooded three weeks later.
By 1982 she had been banned from the High Court, and had spent much of her fortune on legal fees. Her litigiousness was so excessive that, on 5 March 1987, the High Court declared her to be a "vexatious litigant", preventing her from commencing any further legal actions without the permission of the Court. In 1988 following bankruptcy proceedings she lost her home in Bray, to which she returned the following night to recover her love letters from Moore. Her last concert was in 1990, to pay her Community Charge (poll tax).
Squires was provided with a home in Trebanog, Rhondda, South Wales by a fan, Esme Coles. Squires retired there a recluse, and died in 1998 of lung cancer, aged 83, in Llwynypia Hospital, Rhondda. Her remains are interred in a family plot in Streatham Park Cemetery, south London."I'm Walking Behind You" (1953) – UK Number 12
"Say It With Flowers" (1961) – UK Number 23 (with Russ Conway)
"For Once in My Life" (1969) – UK Number 24
"Till" (1970) – UK Number 25
"My Way" (1970) – UK Number 25
On 20 May 2013, a commemorative blue plaque was unveiled outside Aston House on New Road in Llanelli, where Squires and her family took up residence in her fifteenth year. Financed by Roger Moore, the plaque had been created 18 months previously. The unveiling was performed by Ruth Madoc, who was portraying the older Dorothy Squires in the play, Say It With Flowers, by Meic Povey and Johnny Tudor. Following its premiere engagement at the Sherman Cymru Theatre, Cardiff, in 2013, the play toured across Wales. A previous staged tribute to her, Dorothy Squires: Mrs Roger Moore, written by Richard Stirling and starring Al Pillay in the title role, had premiered at the White Bear Theatre in London on 6 June 2012, with a subsequent engagement at the Edinburgh Festival Fringe in August that year. Welsh singer-songwriter Christopher Rees wrote a tribute song to Dorothy Squires, 'Alright Squires', which appeared on his 2013 album 'Stand Fast'.Stars in Your Eyes (1956)