Cliff Richard's 15 greatest songs ever, ranked

26 September 2022, 14:45

Cliff Richard: full interview!

By Mayer Nissim

We round up the very best of Sir Cliff's 150 odd singles in his stunning 70-year pop career.

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Nestled just behind The Beatles and Elvis Presley, Sir Cliff Richard is the third-biggest selling artist in UK history, with over 21 million singles sold.

He's been going for over 70 years now, and Sir Cliff was the only artist to have at least one Top 40 singles in each of the first six decades of the charts.

So it's far from easy to whittle down all those hits to just 15 songs, but that's what we've done.

From his earliest 1950s released through his '60s heyday and some more recent hits, here's our personal spin on the very best of Cliff Richard.

  1. Congratulations

    Cliff Richard - Congratulations (Eurovision Song Contest, 1968)

    Sir Cliff has an often unfair reputation for being a bit cheesy. 'Congratulations' is one of those songs that is pure fromage, but we love it all the same.

    Written by Bill Martin and Phil Coulter, it was originally titled 'I Think I Love You' by Martin before Coulter made the all-important change.

    The song was the runner up in the Eurovision Song Contest in 1968, missing out to the Spanish entry. Rumours still persist today that the fix was in to help out the Franco dictatorship.

    The song went all the way to number one in the UK and Spanish charts, for what it's worth.

  2. Mistletoe and Wine

    Cliff Richard - Mistletoe And Wine (Official Video)

    Sir Cliff has become synonymous with Christmas over the years (he's even got a new Christmas album coming). He's had seasonal chart toppers in multiple decades, ranging from the faithful 'Saviour's Day' to the quirky-as-can-be 'Millennium Prayer' which mashed up The Lord's Prayer and Auld Lang Syne.

    His ultimate Christmas song is maybe his 1988 smash 'Mistletoe and Wine' which topped the charts and was the biggest selling single of the year.

    Although Cliff made it famous, 'Mistletoe and Wine' first featured in the stage musical Scraps in 1976, with that production based on the Hans Christian Andersen's The Little Match Girl.

  3. Carrie

    Cliff Richard - Carrie (Official Video)

    By the end of the 1970s the UK had gone through rock 'n' roll, The Beatles, psychedelia, disco, prog, punk and the rest, and through it all there was Cliff Richard.

    This dark, mysterious track from 1979's Rock 'n' Roll Juvenile was one of many hits from that album, going as high as number four in the charts.

  4. Bachelor Boy  

    Cliff Richard / The Shadows - Bachelor Boy (Together 1984)

    Written by Richard with his Shadows bandmate Bruce Welch, 'Bachelor Boy' was the song that launched a thousand headlines thanks to Sir Cliff's own well-stated reluctance to get married.

    It was actually the B-side to 'The Next Time', but emerged as the bigger hit of the two over the years after its release in 1962.

  5. Don't Talk to Him

    Cliff Richard - Don't Talk To Him (It's Cliff Richard, 31.08.1974)

    Music by Shadows guitarist Bruce Welch. Words were an early effort from Cliff Richard, who agreed to "have a go" despite his nerves.

    It worked, going all the way to number two and keeping Cliff and the Shadows excellent '60s run going.

  6. Miss You Nights

    Cliff Richard - Miss You Nights (Official Video)

    Written and first recorded by Dave Townsend, his version remained unreleased when Island Records shelved Dave's planned album.

    The song found its way to Cliff via Bruce Welch, and it helped launch his comeback, peaking at number 15 in the UK singles charts in 1976. A double-A-side re-release with 'All I Have To Do Is Dream' did one better in 1994, reaching number 14.

  7. Please Don’t Tease

    Cliff Richard & The Shadows - Please Don't Tease (The Cliff Richard Show, 30.07.1960)

    Written by Bruce Welch with his former The Five Chesternuts banmate Pete Chester, 'Please Don't Tease' became Cliff and the Shadows third number one single on its release in 1960.

    It ended up selling over 1.5 million copies around the world.

  8. Travellin’ Light

    Cliff Richard & The Shadows - Travellin' Light (Cliff!, 23.02.1961)

    'Travellin' Light' was the first release by Cliff Richards and The Shadows after they changed their name from Cliff Richard and The Drifters (to stop any confusion with the already-successful US group of the same name).

    It didn't change a winning formula though, becoming Sir Cliff's second number one single, seeing out the decade in style.

  9. Summer Holiday

    Cliff Richard / The Shadows - Summer Holiday (Together 1984)

    Taken from the 1963 film (and album) of the same name, 'Summer Holiday' was one of the many, many Cliff Richard number one singles of the decade.

    Directed by Peter Yates, Cliff Richard led an all-star cast of British talent in the film, including the likes of (deep breath) Lauri Peters, David Kossoff, Ron Moody and The Shadows and features Melvyn Hayes, Teddy Green, Jeremy Bulloch, Una Stubbs, Pamela Hart, Jacqueline Daryl, Madge Ryan, Lionel Murton, Christine Lawson, Wendy Barry and Nicholas Phipps.

  10. Living Doll

    Cliff Richard & The Shadows - Living Doll (The Royal Variety Performance, 22.05.1960)

    'Living Doll' was the first number one single from Cliff Richard and the Shadows – still known then as Cliff Richard and the Drifters – and has an incredible backstory.

    The song was written by Lionel Bart (he who created the musical Oliver!) for the movie Serious Charge.

    It was written as a rock 'n' roll song and that's how Cliff played it in the film, but he point blank refused to record it that way as the contractually-mandated single, thinking it sounded fake compared to the real rock 'n' roll coming from the US.

    So he and the drifting Shadows recorded it as a lower-tempo, country-ish number, and scored their first charttopper in the process. It went to number one again in 1986 when Cliff reunited with Hank Marvin and re-recorded the song with cast of anarchic sitcom The Young Ones.

  11. Wired for Sound

    Cliff Richard Wired For Sound

    Cliff Richard saw in the 1980s with the album I'm No Hero, but his first album that really feels like the decade was its 1981 follow-up Wired for Sound.

    Written by Alan Tarney and BA Robertson, its lead single and title track was an absolutely massive smash, going to number four and selling over a quarter of a million copies.

    Its iconic video saw Cliff in roller-skates, listening to a Walkman at Milton Keynes Shopping Centre. None more '80s.

  12. The Young Ones

    Cliff Richard - The Young Ones (75th Birthday Concert, Royal Albert Hall, 14 Oct 2015)

    Talking about The Young Ones, 'The Young Ones' was the title track from the 1961 movie that starred Cliff as aspiring singer Nicky who wants to save his West End youth club from a dastardly property developer.

    The single went straight in at number one on its release with pre-orders of over half a million, and eventually sold over 2.5 million copies around the world.

    It was of course the theme song to the 1980s sitcom of the same name, in a very different style.

  13. Devil Woman

    Cliff Richard - Devil Woman (Official Video)

    Written by Terry Britten and Christine Authors, Sir Cliff took Devil Woman to number nine in the UK in 1976.

    More impressively, he scored his first US top 20 hit with the song, eventually reaching number 6 and going Gold in the process.

  14. Move It

    Cliff Richard & The Shadows - Move It (The Cliff Richard Show, 19.03.1960)

    Where it all began for Cliff Richard and The Drifters.

    Written by the band's guitarist Ian Samwell, it was originally supposed to be the B-side to 'Schoolboy Crush' but was too good for that fate.

    Instead, it became the A-side of Cliff's debut single, and turned him into an overnight star, reaching number 2 on the UK singles chart.

    More than that, it was arguably the first real rock 'n' roll song that came outside its US home and kickstarted the British rock revolution.

    On the original recording, Cliff sings the same verse twice, as Samwell hadn't finished writing a second one.

    He finally got that remedied in 1995, and Sir Cliff and Hank Marvin re-recorded the song with that extra verse for that year's Hank Plays Cliff, and that's how Richard plays it in concert now.

  15. We Don’t Talk Anymore

    Cliff Richard - We Don't Talk Anymore (Official Video)

    Another Cliff Richard charttopper, 'We Don't Talk Anymore' enjoyed four weeks at number one in 1979, cementing his legacy as an era-straddling star.

    It was his tenth number one single, and his first since all the way back in 1968 with 'Congratulations'.

    Its US success made him the the first act to reach the Hot 100's top 40 in the 1950s, 1960s, 1970s and 1980s.