Cliff Richard ‘plied Cilla Black and Paul O’Grady with booze’ on ‘uneasy’ vineyard trip

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The Millenium Prayer crooner celebrated his 80th birthday two months ago but shows no signs of retiring, a word he claimed was “not in my vocabulary”. He was interviewed on Alan Titchmarsh’s ITV show Love Your Weekend today after the release of his new book The Dreamer and album. The wilder side of Sir Cliff, who was knighted by the Queen in 1995, was revealed by two of his close celebrity friends. 

Sir Cliff met Black on Top of the Pops during the Sixties, when she had released “two wonderful number ones” – Anyone Who Had a Heart and You’re My World. 

They bumped into one another multiple times over the years at various functions and later she “became a great friend” to him, when they both lived in Barbados. 

Black bought an apartment there, months before her husband Bobby Willis died of lung and liver cancer at a London hospital in 1999, and soon after the two bonded.

Sir Cliff claimed to have become her “chauffeur” because they were regularly invited to the same parties and he grew to “love Cilla’s company”.

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He “was in awe” of her music and was impressed that she was able to make the jump to TV, where she became one of the nation’s most beloved figures.

Black’s shows included Blind Date and Surprise Surprise, where her synonymous catch phrase a “lorra lorra laughs” became well known.

When Sir Cliff quizzed her about her matchmaking abilities, she confessed to having spied on the hopeful daters as they rehearsed their answers for the show.

She died from a stroke at the age of 72, which her autopsy report concluded had followed a fall at her Spanish holiday home, in Estepona, in 2015.

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Sir Cliff described her as “funny and smart” and someone who could “always put everybody at their ease”.

Comedian Paul O’Grady accompanied the singers on some of their outings and recalled once being invited to Sir Cliff’s vineyard.

During a 2015 interview on BBC’s Radio 2, the Lily Savage actor described their antics. 

O’Grady said: “When I went over to see Cilla in Barbados, yeah we had dinner. And he’s a very generous host, Cliff. 

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“Did you know he’s got a vineyard? So he just plies you with booze.”

O’Grady was known to have enjoyed the wilder side of life with Black in the past and that they partied in spots less-than-befitting of celebrities.

He said: “Cliff, I used to go into quite dicey nightclubs with her in New York. I’d say, ‘Cilla give us the Tom’ meaning the jewellery.

“Then all the jewellery would come off and I’d have like a million pounds worth of jewellery in my pocket.”

O’Grady admitted that he felt uncomfortable while under-the-influence with Sir Cliff and hinted that it was due to the singer’s Christian beliefs.

He said: “Do you know what it is… it doesn’t feel right being drunk in front of Cliff Richard, it’s like swearing in church.”

O’Grady honoured Sir Cliff and Black’s friendship in a tribute after her death on a BBC Radio 2 show. 

He played their duet of Imagine, as well as Elvis Presley’s song Trouble, which “she absolutely used to love” and “summed up” their friendship.

At Black’s funeral, Sir Cliff opened the service with Faithful One, which he believed was one of her favourite tracks, in honour of their friendship.

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