Dorothy Squires, the powerful Welsh singer known for her dramatic life and equally dramatic performances, left an indelible mark on the UK music scene. Her story is one of staggering heights and devastating lows, mirroring the intensity found in her unforgettable rendition of Dorothy Squires My Way. Once the highest-paid female singer in Britain, her journey from a Welsh village to the grand stages of London, and her subsequent struggles, paint a picture as compelling and tumultuous as her signature song.
From Welsh Roots to UK Stardom
Born Edna May Squires in Pontyberem, Carmarthenshire, Wales, in 1915 (contrary to popular myth, not in a carnival caravan), her early life involved working in a tin plate factory. It was there her vocal talents began to emerge. Driven by ambition, Squires moved to London to pursue a stage career. In the 1930s, she teamed up with songwriter and bandleader Billy Reid, a partnership that brought significant success. They dominated radio waves, record sales, and club circuits for several years.
Following World War II, Squires became a household name thanks to her regular appearances on the popular BBC radio show Variety Bandbox. This exposure propelled her to become the highest-paid female singer in the UK during that era. She scored numerous hits in her homeland, several of which found even greater success when covered by American artists. These included “A Tree in the Meadow” (a hit for Margaret Whiting), “The Gypsy” (popularized by The Ink Spots), and “I’m Walking Behind You” (recorded by Eddie Fisher). Witnessing her songs become major hits for others across the Atlantic added another layer to her already complex career trajectory.
Hollywood, Roger Moore, and a Shifting Career
Dorothy Squires’ personal life took a dramatic turn in the early 1950s when she met and fell deeply in love with a young actor named Roger Moore, who was 12 years her junior. Squires used her established position to help launch his career, taking him to Hollywood and introducing him to influential figures like Gary Cooper, Grace Kelly, Doris Day, and Rock Hudson.
In a narrative reminiscent of A Star is Born, but in reverse, Moore’s acting career began to ascend just as Squires’ singing career started to wane. Their relationship grew increasingly contentious, leading to a split in 1961. However, showcasing a tenacity that would later manifest in numerous legal battles, Squires refused to grant Moore a divorce for years. He was unable to remarry until 1969 – reportedly, the divorce was finalized on the same day Squires was arrested for drunk driving. While documentation is limited, some accounts suggest that struggles with substance abuse may have significantly contributed to the singer’s difficulties during this period.
The Powerful Comeback: Dorothy Squires’ “My Way”
Despite personal and professional setbacks, Dorothy Squires orchestrated a remarkable comeback in the late 1960s. She managed to place three singles back into the UK Top 40 charts. Among these was her rendition of “My Way.” Her version was anything but subtle; it was a force of nature, a performance delivered with such ferocious intensity and scale that it made other powerful interpretations seem restrained by comparison. This period also saw her return triumphantly to the stage with a series of successful concerts at the prestigious London Palladium, two of which (from 1970 and 1971) were recorded and released.
Welsh singer Dorothy Squires performing in a distinctive pink dress during her late 1960s / early 1970s comeback era
Her performance of “My Way” became emblematic of this era – defiant, powerful, and utterly unique. It captured the essence of a performer who, despite facing numerous adversities, insisted on doing things her way, resonating deeply with audiences who admired her resilience.
A Life Consumed by Lawsuits
The comeback’s momentum, however, was eventually overshadowed by Squires’ increasing involvement in litigation. Starting in 1971, she embarked on what would become a staggering series of lawsuits – estimated to be around 30 in total – that would dominate the remainder of her life. These legal battles depleted her finances and forced her into a nomadic existence. Tragedy struck in 1973 when her mansion burned down; she reportedly escaped with only her dog and treasured love letters from Roger Moore.
Her propensity for suing became so pronounced that by the late 1980s, the courts declared Dorothy Squires a “vexatious litigant,” a legal designation used to curb individuals who persistently initiate meritless lawsuits. By this time, she was impoverished but remained defiant. Financial ruin culminated in bankruptcy in 1988, leading to the loss of her home.
Later Years and Legacy
In her final years, Dorothy Squires lived in the Rhondda Valley, South Wales, residing in a house provided by a devoted fan. She passed away from lung cancer in 1998. Despite the turbulence and controversies, Squires is remembered by many for her undeniable talent and formidable spirit.
Perspectives from those who knew her paint a picture of a complex woman. Fan Chris Rogers noted she was beloved by diverse audiences, possessed a “wonderful” personality despite her struggles, and stood at a petite 4’10”. He described her as a “lady with grit,” an assessment supported by her enduring influence on younger artists, including reportedly Adele. Her powerful voice, dramatic life, and the sheer force of personality captured in performances like Dorothy Squires My Way ensure her place in entertainment history as a truly unforgettable figure.
