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Sir Cliff Richard (real name Harry Webb, 1940-) is a singer and entertainer who has managed the feat of a British number one hit single in every decade from the 1950s to 1990s. One of the most enduring icons of British showbusiness, Cliff began his career billed as England's answer to Elvis Presley, and indeed was a cutting edge figure in the Rock and Roll era who made some genuinely good memorable music in that idiom. He fronted a band called the Shadows, who after he went solo, re-invented themselves with some success as an instrumental guitar group. Outshone in the 1960s by The Beatles and other beat groups, his career never went belly-up, and he reinvented himself with some success as a TV presenter and celebrity. Music never went away, and he remains popular as a middle-of-the-road singer, although possibly as un-known outside Britain as Johnny Halliday is outside France.

Cliff has in fact had moderate success in the USA, but unfortunately not enough to establish him as a household name there. In his career he has had eight US Top 40 singles, including the million-selling "Devil Woman", and "We Don't Talk Anymore", the latter becoming the first to reach the Hot 100's top 40 in the 1980s by a singer who had been in the Billboard top 40 in the 1950s, 1960s, and 1970s.

In Europe, Sir Cliff Richard has represented the UK at the Eurovision Song Contest twice. In 1968, he finished second with "Congratulations" — missing out to Spain's Massiel and her song "La La La La". (There is a suspicion that the politicking for which Eurovision is notorious ensured he missed out on the top slot here: Spanish dictator General Franco, in the middle of a row over Gibaltrar, is said to have personally intervened to ensure Spain's vote did not go to the UK). In 1973, Cliff came third with "Power To All Our Friends".

Outside music, Cliff is probably best known for his intense evangelical Christian faith, and the fact that for a rock singer, he leads a squeaky-clean life involving self-imposed celibacy. This, and the palpable absence of a Lady Richard, has led some to question his sexuality, although this is unfair: celibacy is rare, but is a genuine vocation and lifestyle choice which does not imply gayness. (By definition, in fact, to be celibate precludes any form of active sexual expresssion, hetero or homo.)

As a tax exile from Britain, it has been remarked that as a Christian he knows how to give unto God what is God's, but perhaps requires assistance with giving unto Caesar that which is Caesar's.

His commitment to Christianity is both ridiculed and grudgingly admired — he really does appear to live as he preaches (except perhaps in the matter of shelling out tax) — and he has a legion of devoted fans, who, as with Barry Manilow (a singer in the same ilk) tend to be middle-aged and female.

Cliff Richard provides examples of the following tropes:
  • Christian Rock: He's done a few Christian recordings (often covers of gospel songs) one of was a duet with Van Morrison.
  • Christmas Songs: Sir Cliff has recorded his share of both secular and religious Christmas music, and in fact he's the last artist to occupy the Christmas number one slot with a song that actually has Christian themes.
  • Cunning Linguist: Being born in India, he has some knowledge of Indian languages, which he showed off when he appeared on The Kumars.
  • Lady of Black Magic: The title character of "Devil Woman".
  • The Show Must Go On: Famously he was once in the spectator stands at Wimbledon when rain started bucketing down, calling off the match; he promptly entertained the crowd with an improntu concert. Expect this to be referenced whenever he appears on a show.
  • Something Completely Different: Has reinvented himself several times over the years, such as his 2010 brass instruments-themed album Bold as Brass.
  • Trans-Atlantic Equivalent: He wasn't necessarily the first British answer to Elvis Presley (that was probably Tommy Steele a few years before him) but he was definitely the most successful.