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Dorothy Squires’ “My Way”—From the Toast of London to “Vexatious Litigant”

Dorothy Squires’ “My Way”—From the Toast of London to “Vexatious Litigant”


Welsh songbird Dorothy Squires was once a big star in the U.K. whose sad story reads more like a romance novel by compatriot Jackie Collins. When I learned  that she was born into her parent’s carnival caravan in Pontyberem, Wales in 1915, I immediately flashed on the opening line of “Gypsies, Tramps, and Thieves”— “She was born in the wagon of a traveling show.”  Sadly Dorothy’s life story is as desperate and unnecessarily dramatic as the late-period performance of “My Way” that adorns this post like big pink hood ornament.

Dorothy Squires pink dress
This photograph, most certainly not taken at the London Palladium, is a bit more early-70s alcoholic aunt than toast of London.

Squires’ early history was textbook MGM exposition: after working at a tin plate factory where she began singing, Dorothy moved to London to pursue her dream of going on the stage.  There she connected with songwriter and bandleader Billy Reid in the 1930s and together they enjoyed several years of big success on radio, records, and in clubs.  In fact, thanks to her involvement with a popular BBC radio show called Variety Bandbox in the post-war years, Dorothy Squires was actually the highest paid singer in the U.K.  During this period she had big hits in her home country, several of which became number one hits for other artists in the U.S.: Margaret Whiting’s “A Tree in the Meadow”; The Ink Spots’ “The Gypsy”; and Eddie Fisher’s “I’m Walking Behind You.”  This fact alone could understandably make someone want to drink.

Dorothy’s problems seem to have begun in earnest when she fell in love with James Bond #2 himself, Roger Moore, in the early 1950s.   According to the Wiki bio, Squires took the young actor (12 years her junior) “to Hollywood and introduced him to all the right people, and they partied with Gary Cooper, Grace Kelly, Doris Day and Rock Hudson.”  Before you can say “A Star is Born in reverse,” his career took off and hers started to slide.  The contentious couple split in 1961 but in an early example of the pugnacious tendencies which would further accelerate her downward spiral, Squires refused to grant a divorce and Moore was unable to remarry until 1969, the very day Dot was arrested for drunk driving.  There is some reason to believe that substance abuse may have played a greater role in the singer’s troubles than available accounts might indicate.

Dorothy was able to pull it together for a little comeback in the late-1960s, when she placed three songs in the UK Top-40, including her a tsunami-like version of “My Way” that makes Shirley Bassey’s seem passive and ambivalent, and enjoyed a series of successful concerts at the London Palladium, one of which was recorded.  In 1971 she undertook the first of 30 lawsuits that would consume the rest of her life, squandor her money, and force the singer to move from place to place.  In 1973 her mansion burned down and Dot escaped with only her dog and her love letters from Roger Moore (not a good sign).  Her litigiousness was so excessive that by the late-1980s Dorothy, now poor but still pissed, was labeled a “vexatious litigant” by the courts in an effort to control her compulsive tendencies to sue.  She lost her home in 1988 due to bankruptcy.  A fan in South Wales let her shack up with her until her death in 1998 from lung cancer.  Oy vey.

Here is La Dot circa 1970—perhaps the last moment where she enjoyed any measurable success—with the aforementioned thundering rendition of “My Way,” a performance so large in scope and massive in scale that I’m surprised she hadn’t successfully extorted the song’s author Paul Anka for publishing money by the last bellowing note.  If there has ever been a bigger, more demented, drag-like performance of a popular song performed on national TV by a biological woman, I am sincerely at a loss. Please make sure you are securely fastened into your seat and enjoy the unfortunate Dorothy Squires’ memorable, massive “My Way!”

March 2012 Addendum:  A reader named Chris Rogers from England who both knew and loved Dorothy, wanted me to know that I got it wrong about her.  I want to include his perspective.  According to Chris:

  • Dorothy was beloved by both gay and straight people
  • Despite her demons, Dorothy was a wonderful person
  • Dorothy was tiny—just 4’10” (I think he’s referring to my comment “what’s large and feathered”)
  • Dorothy was a “lady with grit,” and alot of younger artists, Adele for one, cite her as an influence.
  • Dorothy recorded two Palladium concerts, 1970 and 1971
  • She was not born in a caravan [for this I blame Wikipedia completely]

You may also enjoy:

Barbara Cartland’s Album of Love Songs Sung Especially For You and the Cartland/Justin Timberlake Connection


  1. woody
    March 12, 2013 at 1:33 am

    This is beyond! Where did you dig her up? Was it you that was also into Lena Z?

    • David Munk
      March 12, 2013 at 3:03 pm

      Um yes. That was me. C’mon Woody – you read Stargayzing!

  2. Douglas
    March 13, 2013 at 7:32 pm

    Holy crap – that was ferocious! Somehow the audio/video synch glitches made it even better. Loved her voice though. Her costume however looked like she dug up eveything she owned in that color and put it all on at once. Thanks for a fun clip

    • David Munk
      March 18, 2013 at 2:19 am

      Oh Douglas, I knew you’d understand!

  3. Bunny Thomas /Thomas Bunn
    March 22, 2020 at 12:49 pm

    It’s a pity quite a few facts are not recorded here despite the dramatic nature of the article much of which , depending on your contacts with Dorothy over the years – firstly the first major Palladium concert was Dec 1970 it was a smash and vile things said about her by Linda Lee Poter Sge joked about on walking on to the packed venue.
    She was sensational and warmed up more so well into this performance complete with 32 piece orchestra.
    Prior to the first Paladium in late 60’ she did the Llanelli concert near to her old home town . Much what is said one may and can agree with . However my relationship with her as a young 18 year old was never shattered by negativity
    In the Book
    “”Sorry Darling It’s Way Past Time “ I document some of my encounters and the sadder times when I took my mate the late great Larry Grayson to Ackworth where she was holed up Post near eviction from Bray .
    I encountered at times warmth and generosity YES she was never easy . Her personality hiding much paranoia which she exploded with at times. ( she would never have complied with medication ) if she had she would not have been who she was !
    Her funeral at Port Talbot was something else
    and a thank you to Esme Coles If Trebanog
    The last couple of years of her life . Yes she was complex shall we say . Reclusive that last decade ….
    What a life what a woman 👩

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