Sir Cliff Richard, who recently marked his 86th birthday, continues to actively engage with his music career through new projects and collaborations that bridge generations. The veteran British singer has released his 48th studio album, Only Number Ones, which features a cover of Harry Styles’s 2017 hit "Sign of the Times." Though he initially was unaware that Styles was the original artist, Richard expressed enthusiasm about the track and its inclusion on his album.

Richard, whose birth name is Harry Rodger Webb, has amassed 14 UK number one singles over his career, contrasting with Styles’s four chart-toppers since the former One Direction member began his solo career. Speaking about the possibility of working directly with Styles, Richard said he would consider a duet but would first need to understand the musical arrangement, noting that Styles’s vocal key might be higher than his own.

The artist has long been a fixture in the UK music scene, ranking as the third best-selling singles artist in UK chart history behind only Elvis Presley and The Beatles. Richard’s career launched in 1958 with his debut single "Move It," while Styles rose to fame on the X Factor at age 16.

In addition to covering Styles, Richard revealed plans to release a new Christmas song featuring a reggae adaptation of the psalm "The Lord Is My Shepherd." Collaborating with songwriter Chris Eaton—who previously wrote the 1990 holiday hit "Saviour’s Day" for Richard—the singer is experimenting with reggae for the first time, reflecting a willingness to explore new musical styles even after decades in the industry.

Richard also referenced his 1999 Christmas number one "Millennium Prayer," which set the Lord’s Prayer to the tune of "Auld Lang Syne." He expressed admiration for Bing Crosby’s enduring success with "White Christmas," acknowledging that the classic record remains unmatched in sales.

His enduring popularity spans generations, bolstered recently by the inclusion of his 1976 hit "Devil Woman" on the soundtrack of the video game Grand Theft Auto VI. Richard noted that the song tied into a character in the game and delighted younger listeners, including his own nephews, who were surprised to discover his music in a modern context.

Despite his advancing age, Richard shows no sign of slowing down. He recently celebrated his birthday with fans at a London event and remarked on embracing his longevity in the music industry. He attributed his sustained career to staying connected with both his past and present audiences, affirming his intention to keep producing music for years to come.