A teaser for Sir Cliff Richard‘s 2027 calendar has dropped with a look at the singer’s silly side as he posed in an array of wacky looks from exotic locations.
The pop veteran, 85, has been releasing his annual poses since the seventies and regularly outsells the likes of the former One Direction star and Taylor Swift.
This calendar marks the 49th edition of Sir Cliff’s annual offering, which includes a shot of him sporting a tuxedo T-shirt holding a ‘his lordship’ mug.
Sir Cliff leaned into the psychedelics of the 60s and 70s, sporting a funky rainbow T-shirt and round yellow-tinted sunglasses, posing in front of a series of vibrant bottles.
The latest edition of the calendar also includes a tribute to Sir Cliff’s late friend Cilla Black, who passed away aged 72 in 2015.
A teaser for Sir Cliff Richard’s 2027 calendar has dropped with a look at the singer’s silly side as he posed in an array of wacky looks from exotic locations
Sir Cliff leaned into the psychedelics of the 60s and 70s, sporting a funky rainbow T-shirt and round yellow-tinted sunglasses, posing in front of a series of vibrant bottles
The latest edition of the calendar also includes a tribute to Sir Cliff’s late friend Cilla Black, who passed away age 72 in 2025
Sir Cliff, who was wearing a tie dye jacket and shorts, stood at the back of the boat with the name ‘Cilla’ and two glasses of champagne.
Sir Cliff and Cilla had a very close, long-lasting friendship, from when they first became friends in the 1960s, when both were among Britain’s biggest pop stars.
Their friendship lasted for around 50 years and continued well beyond their chart success into their television careers.
They spent time together in Barbados, where both owned homes, and were also seen dining together in places like Marbella, which are likely where Sir Cliff’s snaps for this year’s calendar were taken.
Speaking about the calendar, Sir Cliff said: ‘My favourite pastimes are travelling and spending quality time with friends and the pictures in the 2027 calendar are a small snapshot of some wonderful times in May and June this year in various locations.
‘I am delighted to be sharing these with you in my 2027 calendar, of which, I am so proud. It might be a bit early but a happy 2027 to you all.’
Sir Cliff’s total calendar sales since 1979 are reportedly around the £2million mark – beating the likes of David Beckham.
His 2022 release was the best-selling of any music star’s calendar, according to Calendar Club, which had Elvis Presley in second, followed by Styles.
Sir Cliff was reading a book titled It’s Great To Be Young which he authored
Sir Cliff’s 2026 calendar is now available here
Sir Cliff and Cilla had a very close, long-lasting friendship, from when they first became friends in the 1960s, when both were among Britain’s biggest pop stars
In one image, Sir Cliff proves he knows exactly how to give his fans exactly what they want, by offering up two images of himself sat on a chair in front of the sea.
Danilo Promotions, which tracks sales of all calendars, put Sir Cliff’s 2024 in fourth, with Taylor Swift top. Harry Styles didn’t make the top five.
In 2023, the singer left fans disappointed when he announced that he would be breaking with tradition by not stripping for his calendars going forward.
Fans had become accustomed to him posing topless, as he did in a swimming pool in 2022.
‘I suspect I have done my final topless photo for my annual calendar… it’s time to gracefully exit the Chippendales market,’ he said.


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